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WikiProject Chemistry (Rated Project-class)
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Discussion of the WikiProject Chemistry - Please add your comment and discussion here. Older discussions are archived.


This discussion page is about the Chemistry project itself, for detailed, in-depth discussions about specific topics, you'd be best served at the talk page of the specific subject, e.g., Chemicals, Chemical infoboxes, etc. There is also an image request page which might be of interest to you.


European Commission number[edit]

What shall we do with this edit/information? --Leyo 01:22, 5 January 2014

Nobody? --Leyo 21:23, 9 January 2014

Wikipedia talk:Articles for creation/Salt-water batteries[edit]

Dear chemists: This Afc submission was declined because there is another article in mainspace, Salt battery. Should salt-water batteries have a separate article, and if not, is there content that should be transferred to the mainspace article from this draft? —Anne Delong (talk) 02:47, 15 April 2014 (UTC)

Don't have time to look deeply now, but I think the pre-existing item Anne means is Salt battery, which is a redirect to Molten salt battery. On their face, salt-water vs melted salt are different things. DMacks (talk) 03:18, 15 April 2014 (UTC)
Sorry, yes, I dropped a letter. For salt batter I would have notified the Food and Drink guys! I thought the two topics looked different, but I'm no chemist. I have postponed the deletion of the draft for six months. Is it properly referenced for mainspace, or does it need improvement?
From the content, it seems like they are describing a simple Galvanic cell or Electrochemical cell that uses salt water as its salt bridge. Maybe we can set up a redirect for Salt water battery to Galvanic cell or Electrochemical cell (I'm not sure which is more appropriate) if that's a common search term. 0x0077BE [talk/contrib] 14:55, 15 April 2014 (UTC)
DMacks and 0x0077BE, is there any useful content in the draft that should be moved to one or the other of these articles? —Anne Delong (talk) 01:24, 20 April 2014 (UTC)
I don't think there's anything salvageable, and the specific title seems an unlikely search-phrase. The only novel claim is the "Water Salinity Difference" item in the "Future of Salt-Water Batteries" section, but it's fairly preliminary primary research (interesting and novel, but doesn't yet appear to be noticed by other reliable sources). DMacks (talk) 17:51, 25 April 2014 (UTC)
i'm not sure where to start on how confused it is (talk) 03:05, 25 April 2014 (UTC)
I agree. There is a lot of weird stuff there, as well as some kernel of topic already covered elsewhere. DMacks (talk) 17:57, 25 April 2014 (UTC)
Okay, it has faded away... —Anne Delong (talk) 01:46, 12 May 2014 (UTC)


The article alkylimino-de-oxo-bisubstitution was originated by a respected editor, but this title is IMHO just too awkward. Many of us have lots of experience with imines and Schiff bases, but, I have never ever heard of the mouthful alkylimino-de-oxo-bisubstitution. Almost sounds like a joke. So I am wondering if this material might be better blended into imine. Since there is occasionally resistance to mergers, alternative ideas are welcome. BTW, if anyone knows the difference between "imine" and "Schiff base", please leave a note here! --Smokefoot (talk) 16:20, 19 April 2014 (UTC)

I could support merging to imine (and/or hemiaminal). It might be the technically correct name based on systematic rules for the reversible N/O substitution, but I don't think there's sufficient content specific to this reaction or notability of it itself, rather only in its application to carbonyl/hemiaminal/imine interconversions. The content in the article beyond the mechanism is interesting (the geometry of the aziridine, the color-changing upon thiol cyclization), but seems cherry-picked. OTOH, that latter one could go into the imine article, as there are no S-attack reactions in the "reactions of" section, and maybe also as an Baldwin's rules example. DMacks (talk) 04:20, 29 April 2014 (UTC)
for once I agree with IUPAC , the name originates with them and was then adopted by March and that is how I learned of it. A Joke? Poor Jerry March. Every organic chemistry textbook has this reaction type so notability ensured. Why not an alternative name. Organic Mechanisms: Reactions, Methodology, and Biological Applications / Xiaoping Sun suggests "nucleophilic addition of amines to ketones and aldehydes". A lot of pages exist in wikipedia with a name like that. Further: we have a lot of pages on functional groups and we have a lot of chemical reaction pages that link between them. it makes sense to keep it that way. The aziridine case seems relevant. The scope example is exactly what it is: an example. Details can be demoted to notes. I do not understand the cherry picking comment. V8rik (talk) 19:37, 17 June 2014 (UTC)
We are involved in an experimental science: walk down your hallway and ask your friendly organic chemist to name or describe the condensation of an amine and a carbonyl to give an imine. Seems pretty unlikely that you'll this response "Oh, you mean the alkylimino-de-oxo-bisubstitution!" For that reason, it seemed reasonable to contemplate putting this content into an article that would come up in searches. As a service to readers vs obedience to IUPAC. So my thought is nothing to do with owning an article or anti- or pro merger thoughts, it is solely about helping readers who want info on imine condensations. We run this reaction often, and I have yet to hear this term. But maybe I need to ask around. Not a big deal. --Smokefoot (talk) 23:10, 17 June 2014 (UTC)
  • let me restate my enthusiastic support for a name change. I have already made one suggestion. Anyone else? V8rik (talk) 15:31, 18 June 2014 (UTC)

Other names as redirects[edit]

Is there a way that "other names" in the Chemboxes could automatically be made into redirects to the same topic? --Smokefoot (talk) 16:20, 19 April 2014 (UTC)

I don't understand this. Could you give a specific example or two? DMacks (talk) 16:43, 30 April 2014 (UTC)
Well in the Chembox, there is typically a list of other names for a compound. Like here:
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Maintenance categories
+cat:No image, no structure drawing (image checks)
+cat:Unverified chembox (verification)

It would be very nice if "Becton White" automatically became a redirect to "lithopone" by virtue of being in the "other names" section. Does this make sense? --Smokefoot (talk) 17:10, 30 April 2014 (UTC)

So when someone added "Becton White" to that list, Becton WhiteLithopone would be automatically created? Interesting! If it's listed, then searching should already find it (as text) even without having an actual article (-redirect) at that name. But it would help for other articles that have links to the alt names. Seems a little ripe for abuse IMO (might want to have a delay to allow antivandals to revert any bad entries). And many of the entries in the example here don't seem like worthwhile links (different concentrations, or adjectives added to chemical names). Maybe a bot could collect them and list the non-existing ones for manual triage? DMacks (talk) 17:21, 30 April 2014 (UTC)
It will never be automatically, like fixing double redirects (automatically) is turned of. But the template could check if the page exist. Christian75 (talk) 08:08, 22 May 2014 (UTC)

Royal Society journals - subscription offer for one year[edit]

I'm delighted to say that the Royal Society, the UK’s National Academy for science, is offering 24 Wikipedians free access for one year to its prestigious range of scientific journals. Please note that much of the content of these journals is already freely available online, the details varying slightly between the journals – see the Royal Society Publishing webpages. For the purposes of this offer the Royal Society's journals are divided into 3 groups: Biological sciences, Physical sciences and history of science. For full details and signing-up, please see the applications page. Initial applications will close on 25 May 2014, but later applications will go on the waiting list. Wiki at Royal Society John (talk) 03:02, 29 April 2014 (UTC)

Fischer Indole Synthesis[edit]

I am writing this to inform you about an error regarding the Buchwald Modification to the Fischer indole synthesis. The initial hydrazone cross coupling occurs between benzophenone hydrazone and an aryl bromide, not the correspondig enolizable hydrazone. The installation of the latter hydrazone occurs as a result of hydrolysis of the benzophenone hydrazone followed by the condensation of the enolizable ketone to ultimately cyclize to form the desired indole. In this way, benzophenone acts as a protecting group for the isolation and handling of the cross coupled intermediate.


Chris Gabriel University of California, Santa Barbara — Preceding unsigned comment added by ChrisMGabriel (talkcontribs) 13:38, 4 May 2014 (UTC)

Here we go again with Plasmic Physics[edit]

Once again User:Plasmic Physics is editing chemistry articles. We has a respite of a few months. In my opinion, the edits are not just weird, often wrong, but they are hurtful to our readership. His edit to the radical cyclopentadienyl is found here: [[1]]. On the same day he changed acetic acid article to point out that the reactive group is the carbonyl, not the OH, see [[2]]. Can some administrator please try to negotiate terms with him again?--Smokefoot (talk) 00:32, 6 May 2014 (UTC)

Note that cyclopentadienyl (a term which readers would mainly find when running into organometallic terms, hence mostly denoting the anion) has over the course of time been rewritten from exactly that (the anion) to the free radical. The free radical is about the last thing a reader would look for, they may run into an organic moiety having a cyclopentadiene ring attached to it (already rather unique in comparison to the anion). IMHO, this article should be strictly about the anion, its bonding to metals. Mentions of the free radical or the organic group should be minimal (if notable at all). Note: I have completely undone the rewrite, which is mainly if not completely by Plasmic Physics, which changed the article from the anion to the radical - it is now back at the anion-state).
I believe both should be covered, and leave it to those with interest to determine where. Encyclopedias cater to interest, but also lay out the landscape in intellectual areas, and so the radical species, as it exists in good secondary literature, should appear, however short the section might be. Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
I have reverted the acetic acid edit. The man in the street is familiar with acetic acid and its acidity, which stems from the OH, not from the C=O (one could argue from the COOH, I find it always dangerous to use these terms).
HgH, the other article edited recently, is another difficult one. There is a lot of information added over the course of months, still the references are the same (see here where Plasmic Physics is adding a whole section .. without any references). (following not really due to Plasmic Physics:) One of the three is a Chem. Rev. article by Simon Aldridge, which mentions mercury hydride only minimally. Overall, I found it difficult to attribute the statement to those articles (I think that the attribution to the review is plainly wrong). (now back to Plasmic Physics:) Most of the new information is completely unreferenced, and in the latest edit he changes the 'also written' way to a form which I did not see in the supplied references (he has been edit warring about it in the past, found a compromise which now was removed so it is finally gone). Looking from the reader side, I find it completely wrong.
Agree that acidity should be covered first, but reactivity of the carbonyl is also a central concept (see, e.g., the development of carboxylate reactivity at this esteemed site: [3]. Absolutely concur that an outcome of this (and every) Wikipedia discussion should be to dissuade individuals who add material without citations, and to sanction them if they repeatedly do so, per WP policies on verifiability. This all the more since most chemistry contributors are not graduate trained or professional chemists. Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
Now that writing in a way that is harmful to the reader is recurring. As is the writing of systematic names, systematically writing of formulas, alternative names, etc. As is the lack of references. And the (slow) rewrite of articles to cover a completely different subject is another theme of recurrence (here mentioned in cyclopentadienyl, in a way it is also in mercury(I) hydride, though that was not too established and maybe plainly incorrect in the beginning) and even worse than harmful. I regard the bold rewrite of cyclopentadienyl to be close to destruction of the article, extremely harmful to the reader and to Wikipedia, and if Plasmic Physics does not understand that, I think that a long ban from all chemistry related subjects, broadly construed, is in place. --Dirk Beetstra T C 04:10, 6 May 2014 (UTC)
I do not know the history of this matter, nor have I time to enter into it. I would say that the issues being raised are very important; though the editor appears well meaning. Perhaps he will respond to a final warning to (i) make no substantial edits without clear evidence that reflect the preponderance of professional chemistry opinion as evidenced in the best texts and secondary references, and (ii) that, given his apparent history with this community, he place a note in the talk page discussing significant proposed edits prior to editing (a rarity here, but something I routinely practice). If he does not respond to such, then perhaps, if indeed there is a long disruptive history, he will have to experience a block to understand that consensus is required (and that his antennae for sensing whether his edits will achieve consensus post hoc are seriously mistuned). Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
Plasmic Physics undid my revert of the change in Acetic acid (diff), changing the sentence "The OH group is the main site of reaction, as illustrated by the conversion of acetic acid to acetyl chloride." to "The CO group is the main site of reaction, as illustrated by the conversion of acetic acid to acetyl chloride". His argument: "Incorrect, OH is predominantly involved in acid dissociation." We are not talking about acid dissociation, the only conversion that is illustrated by the change of -COOH to -COCl is the .. change in the OH group into a Cl group. I hence stand with my suggestion of a long term restriction from Chemistry articles, broadly construed. --Dirk Beetstra T C 11:10, 6 May 2014 (UTC)
Disagree. The formation of acid chlorides is perhaps best described as going through a pericyclic transition state, and this reactivity clearly involves the carbonyl as well as the acidic proton (see [4], a site run in conjunction with the fine Clayden text); the same is true of the PCl5 mechanism. Note, formation of acid halides, anhydrides (e.g., with P2O5 or modern methods), etc. are generally done under anhydrous and apolar solvent conditions, suppressing formal deprotonation/oxyanion formation as a prior discrete step to further reactivity—no? Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
  • I support banning Plasmic Physics from editing chemistry. I just dont see any upside to his participation. If he is banned from chem and moves to another project, god help that project! --Smokefoot (talk) 12:36, 6 May 2014 (UTC)
This is a rush to judgment and I do not agree. Blocks and bans are serious steps. Annoyance is simply not enough. Edit conflicts can (and judging by the following discussion) post hoc will in this case actually serve to improve content. Silencing a dissenting voice in the case of the issues appearing here may make things more peaceful, but they will not automatically provide the highest quality content. And that is the aim, no? Bottom line, this community has not shown me either that it is rightly adjudicating the science, or that it has exhausted other less extreme actions aimed at shaping editor behaviour. Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
  • Just to comment on the specific edit to Acetic acid that is being discussed Plasmic Physics is right that in the conversion of acetic acid to thionyl chloride is a substitution of an OH with a chloride with the carbonyl as the reacting centre. I can try and source a reasonable off wiki source but for now I'd cite [[5]] see the Carboxylic acids section which shows the mechanism - I'd actually suggest that this conversion from acid to acid chloride is less than ideal as it isn't a good example: it is less straightforwards than an a basic esterification. And relating to the point Dirk Beetstra is making; carboxylic acids tend to undergo acid-base reactions over substitution reactions unless you start to look at more complicated mechanisms/reagents. So I guess I'm saying both points are correct and it is probably that the content in this section needs re-working to make it clearer (rather than this small edit about where is reacting.) --The chemistds (talk) 12:53, 6 May 2014 (UTC)
Astute comments, see above for linked site in support of this User's claim. Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
  • A few observations: (1) Plasmic has produced a lot of disruption over time, but he's not always wrong; (2) On cyclopentadienyl, he is correct that the name is not correct for the isolated anion but rather for the radical or the anion when it is a ligand. I would suggest a making cyclopentadienyl a dab page linking to an anion page (under cyclopentadienide which is already a redirect, adding redirects from cyclopentadienyl ion and cyclopentadienyl anion and borrowing from the current page as Beetstra prefers it), a complex page (which already exists) and a page at cyclopentadienyl radical using material from the Plasmic version. The substituted cyclopentadienyl radicals are well known as reactive intermediates in this area of chemistry; (3) on acetic acid, it is bad practice to refer to a carboxylate functional group as a carbonyl and a hydroxyl, it strikes me as similar to arguing about whether walking is centred on the ball or the heel of the foot. EdChem (talk) 13:25, 6 May 2014 (UTC)
Astute comments, though the -yl form is acceptable if followed by anion, and indicative of the radical if not. Otherwise, kudos, well spoken. Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
Comment: Yes, cyclopentadienyl is the name for an (esoteric) radical. But look at what Plasmic did to it recently Edits made by Plasmic often have some element of fact to them, the issue is with persistent abuse of WP:UNDUE and persistent (and I really mean persistent) problems with imposing weird nomenclature. His work often relies on narrowly selected literature to support his flawed grasp of chemistry. --Smokefoot (talk) 13:39, 6 May 2014 (UTC)
Esoteric, no. I am neither a radical chemist, nor an OM chemist, but an OChem/medichemist and educator, and say, strongly, both definitions belong in an encyclopedia. That, at this moment of history, in the literatures that this group are most fluent, the anion is most prevalent, does not speak to fundamental importance of the anion, nor does it support exclusion of the important observation that the -yl radical can be formed from the parent hydrocarbon. Indeed, in the history of physical organic chemistry, both are equally and seminally important (insofar as understanding organic structure and bonding, molecular orbital theory in OChem, delocalization and aromaticity, etc. are concerned). One man's esoteric may well be a fundamental concept on which much deep understanding is based. Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
@Smokefoot: I agree that PP has caused lots of problems, and in saying he is correct I was thinking more of a post he made at Dirk's talk page than his changes to the article. Certainly his nomenclature work is irritating (at best) and his grasp of chemistry is highly variable. I thought the last time he started taking large actions that a topic ban would be appropriate, and I am not opposed to it, but I maintain that he has a point here and put forward an option that would both direct readers correctly and be chemically acute. I also just changed where the thallium cyclopentadienide article was linking Cp to cyclopentadiene and my suggestion would provide better targets. EdChem (talk) 13:51, 6 May 2014 (UTC)
Again, if the standard is that there is to be no substantial editing by PP or the rest of us, without addition of relevant, quality 2o or 3o citations, then the nomenclature editing problem goes away. There is absolutely no excuse in this decade of this millennium for nomenclature issues to be contentious; every such entry can and should be supported by (i) an IUPAC citation (online, for heaven's sake), and then a second practical reference. e.g., to a high quality teaching text like Clayden, or to an industrial chem guide, as is relevant. (The latter, because IUPAC tries to shape what practicing OChemists do in their "name-calling", but they are not always successful. That the IUPAC called the recent newsworthy carbinol "(4-Methylcyclohexyl)methanol" is only (just) as important as the fact that the news media and industrial enterprises still know it as "4-Methylcyclohexanemethanol" or "MCHM"—which Wikipedia has, thankfully, gotten correct.) Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)

My next 2p. If people in newspapers, on internet, wherever encounter the term 'cyclopentadienyl' it is always consistently with respect to the Cp-complexes of metals. That is what we are writing Wikipedia for, those readers, not for the chemist. Even if that cyclopentadienyl does not follow the systematic IUPAC naming, it is what we chemists say, it is what chemicals companies call compounds with it, and it is what newspapers would say when referring to cyclopentadienyl-containing compounds. If that reader types into Google 'what is a cyclopentadienyl', they expect Wikipedia to come up with that term for this anion. Not for the free radical, not for the functional group (as in an organic compound). I therefore think that Cyclopentadienyl should be about the anion, and there could be dab-links at the top, pointing to the cyclopentadienyl-radical (the free compound) or the cyclopentadienyl-functional group in organic chemistry (if that has enough body to have an article). It may not be chemically/IUPAC 100% correct, but I firmly believe that that is what the reader expects to find when they look for cyclopentadienyl after they encounter the term somewhere (making it a disambig will only confuse them). (by the way, I think that Thallium cyclopentadienide is a bad example, it redirects to Cyclopentadienylthallium, with the commonly used, though likely in conflict with the systematic IUPAC rules, cyclopentadienyl). And you see, we are back at the point of nomenclature.

I am sorry, no, Ed, here we disagree. We are writing to shape broad understanding of a field, and to correct as well as to inform as we go. Change the article title to "Cp anion", or make room for both concepts (anion and radical). See my earlier comments about the importance of organic radicals to theory, history, and mechanism in OChem. That google searches pull up the one now is a matter of public popularity only, and not a guidance for science writing! Moreover, Google is a purely commercial enterprise, only the poorest of academic search tools, certainly vis-a-vis chemistry searching; its prioritization of reported hits is not under user control. (Santorum neologism. Need I say more?)
If one wants the real lay of the land, one always uses two separate search tools, and then holds the perceptions generated with an open hand (mind). Search the Cp term in its written out form at the ACS portal, and then in the Beilstein. Yes, you will see the anion, but the radical is also there—and all the more if you constrain searches to particular periods. The overwhelming ubiquity as much speaks to the timing of the emergence of the Cp anion in chemistry relative to emergence of the internet, as it does to anything fundamental to chemistry. As well, the best OM chemists (e.g., Bosnich trainees from Chicago) would always speak of the "Cp anion" in formal settings (seminars, papers, etc.), though in lab perhaps truncate the expression. The encyclopedia is such a formal context. Bottom line, the word refers to both organic structures. Either disambiguate "cyclopentadienyl anion" and "cyclopentadienyl (radical)" as IUPAC and all teaching chemists do in formal writing, or make room for both in the one article. Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)

Regarding acetic acid, the example given is confusing, and the mechanism of it is canonical, simplified. Basing on that mechanism the conclusion that the CO is more reactive than the OH is IMHO wrong .. but the core of the problem is not that, I wonder in how far we can correctly say that a -COOH group has a C=O and a C-O-H anyway. And in a way, this is close to the same problem as the nomenclature - this sentence shows thinking of a COOH group as a keto-function and alcohol function. The problem lies deeper. --Dirk Beetstra T C 14:18, 6 May 2014 (UTC)

See my comments above about the cyclic transition state. Agreed, the matter arises because of oversimplification of the reaction mechanism, both at the article and in this discussion. Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
@Beetstra: What I don't understand about your position is that if readers would be seeking "cyclopentadienyl-containing compounds", why not focus on cyclopentadienyl complexes rather than the anion? Maybe we need an article on the complexes with sections on synthesis to discuss the anion and radical? EdChem (talk) 14:34, 6 May 2014 (UTC)
Ed my respect for you grows and grows. Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
I think that the incoming search term from a non-chemist would be 'cyclopentadienyl', not 'cyclopentadienyl complex'. We do not strictly adhere to the IUPAC naming, but to what is commonly used. Cyclopentadienyl is commonly used for the cyclopentadienide anion - practically all our complexes with a cyclopentadienide anion have the term cyclopentadienyl in their (current Wikipedia page-)name. --Dirk Beetstra T C 14:39, 6 May 2014 (UTC)
No further comment on this. Professional opinion clearly stated. Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
In a way, this is what I mean, it is a persistence of Plasmic Physics to align Wikipedia completely with the systematic IUPAC nomenclature and other IUPAC rules. That sometimes conflicts with what is the common use, which is the consensus that we have that we will use ("Generally, article naming should give priority to what the majority of English speakers would most easily recognize, with a reasonable minimum of ambiguity, while at the same time making linking to those articles easy and second nature.", from WP:MOSCHEM/NAME). We don't call the article [[(6R-trans)-6-(1,3-benzodioxol-5-yl)- 2,3,6,7,12,12a-hexahydro-2-methyl-pyrazino[1',2':1,6] pyrido[3,4-b]indole-1,4-dione]] (we don't even have the redirect) - we don't follow the systematic way of IUPAC there, we use the name that the is commonly used, and even the name that is used by most of not all chemists, even if that is in conflict with IUPACs systematic rules. Cyclopentadienyl is the name that mostly denotes the cyclopentadienide anion, unfortunately in conflict with the systematic IUPAC rules. --Dirk Beetstra T C 14:45, 6 May 2014 (UTC)
Apples and oranges, mate, and a straw man argument to boot. To ask disambiguation of anion and radical is not the same as the game-playing you are doing with the IUPAC name for tadalafil. In the one case, the two refer to two different chemical entities, with differing reasons for importance. In the latter, it is a to-may-toes / to-mah-toes issue (or better, a tomatoes / viiniköynnöksen kypsyneitä tomaatteja issue, if you speak FInnish). Let's call the whole thing off, indeed [6]. Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)

I have been following this discussion with some interest. First, I am not happy about how this is being handled. Nobody has seen fit to talk to PP directly on his talk page, even to point him here. Second, I tend to agree with EdChem here, but there could be a variety of solutions. The article could discuss both the anion and the radical, although the discussion of the anion should be first. You should be looking for compromise and ways of educating PP, not just reverting him. --Bduke (Discussion) 22:54, 6 May 2014 (UTC)

I am late in coming to the discussion; if this observation is indeed correct, shame on us. Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
I am sympathetic with the spirit and the letter of your advice. We are here to help not only the readership but each other. But when is enough enough? Review the agonizing process by which User:Axiosaurus and others coaxed borane and related articles from his grip. One needs a tag team to cope with his writing, and he can be a prolific editor. So in terms of your advice of "educating PP", that experiment seems to have been tried, repeatedly. He has been reprimanded for editing chemboxes, nomenclature, categories. Now look at PP's very recent edits of cyclopentadienyl:
"The 2λ3-propane-1,2,3-triyl-1,3-diylidene group (⩾CC(R)C⪕) in 1λ3-cycloalk-2-(di)enes such as cyclopentadienyl can accept or donate a single electron by association:
+ R → R(C
Because of this acceptance or donation of the electron, cyclopentadienyl has radical character. It is a highly reactive monoradical. Its functional group is cyclopenta-2,4-dien-1-yl (-C
He's been an editor for how many years? The lack of PP's progress and the requirement for chaparoning his work are semi-exasperating. Not a crisis, but exasperating.--Smokefoot (talk) 02:05, 7 May 2014 (UTC)
Propose firm boundaries, here: short of a ban or block, what specific constraints would you like, please? Though the edits might be misguided, the chemistry issues are not as simple as were initially represented. What specifically would you like PP not to do? I have suggested some elements of a proposal, that can be cut-paste-edited into your bullied proposal. At this stage, I will fight a block or ban. Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
User:Bduke - Plasmic Physics is not a new editor here. He should know process. Though I agree that he should have been informed about this discussion here (I did mention it to him on my talkpage when he came to discuss .. well rather complain about .. the reverts; did he not get informed? User:Beetstra WP:WIKITROUTs User:Smokefoot (knowing full well that Smokefoot linked Plasmic Physics' username, so he got pinged). It does however not invalidate the discussion, nor make the problem disappear).
Still, shame on us. Was the conscious point of excluding him in notification, to have a private discussion first, to build an inevitable momentum? If so, all the more… Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
Regarding the reverts, I have been reverting with an edit summary. At that point the discussion could commence. When that does not happen but he simply re-reverts then that does not help. And especially with cyclopentadienyl, I again stress, it is the problem that is appears that Plasmic Physics enforces all articles to follow the IUPAC recommendations for systematic naming. That is not how Wikipedia operates, neither is it normal operation that if someone reverts your bold changeover back to the long-standing version that you then engage in reverting. Similar is the changeover to Acetic acid, where his changeover is canonically correct, though chemically senseless (the observer will say 'I thought that acetic acid was an acid, which means in my high-school chemistry that there is a proton (H+) involved .. and now you tell me that the main reactivity is because of the C=O?). And that is actually because there is a deeper problem with that sentence, which does not get recognised.
The "enforces all the articles to follow the IUPAC" matter can easily be addressed in a disciplinary proposal short of a block or ban. And what you are terming senseless is clearly something that I believe, as a career research chemist and educator, involves nuance that you are failing to acknowledge. Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
The common denominator between the cyclopentadienyl and acetic acid situation is that both are 'problems' (they are both in the grey area between two 'correct' situations). Plasmic Physics boldly changed them over from one correct situation to another correct situation, and I recall similar cases from the past (this is not the first time that his prolific work to an article got reverted). The recurring (and exasperating) problem is that Plasmic Physics does not always seem to know the line between 'should I discuss this', 'should I boldly change this', or 'should I leave this as is'. He does great work (albeit a bit too technical, and having some issues from the reader/accessibility side, methylidene is a good piece of information, that is something we can build on), but he should understand that sometimes it is better, especially if it involves long-standing articles on terms which are very common like cyclopentadienyl, to bring his discussions first to a wider audience and wait (and understand that if such a discussion does not come to a close, that that does not automatically needs to mean that there is consensus to change), and if there are changes that are without consensus that get reverted, that then the same discussion-wait-for-consensus-situation should take place. --Dirk Beetstra T C 04:02, 7 May 2014 (UTC)
In re: an emerging proposal, see above for the second of two points, that significant editing be preceded by Talk. Generate a firm, fair disciplinary proposal, based on what you have heard from me, and others that do not completely agree with you. Post that new proposal below. Remember, what is good for the goose, is good for the gander. Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)

The following was posted on my talk page,

There is a long discussion about your edits to chemistry articles at Wikipedia talk:WikiProject Chemistry#Here we go again with Plasmic Physics. I am disappointed to see that you have not engaged there and responded to the criticisms. Please do so, and we might then come to some kind of resolution. Ignoring criticism never helps. --Bduke (Discussion) 06:11, 7 May 2014 (UTC)

To Bduke: I have not engaged, because my input is never regarded. In every case, the outcome have always resulted, irrelevant of it. It usually results in either a stalemate, or a symptomatic involuntary cat-and-mouse resolution, which is evidently non-effective. I say involuntary, because it tends to arise unintended and spontaneously. That said, I do agree for the most part, with Beetstra's interpretation at 04:02, 7 May 2014 (UTC). However, identifying the problem is only one side of the coin. Unless a resolution is devised and implemented, any interpretation is useless. If any one does indeed require my input, then I would appreciate direct questions. Plasmic Physics (talk) 07:29, 7 May 2014 (UTC)

This is not helpful. No wonder, editors here are frustrated. You address none of the issues raised above. Why do you think the quoted paragraph about the radical is appropriate? Why did you change the article from being about the anion to being about the less important radical? Why do you persist in using IUPAC nomenclature strictly when there is a clear consensus in this project to be more flexible to make things more understandable to our readers? I could go on. --Bduke (Discussion) 21:04, 7 May 2014 (UTC)
Stop with the "less important", please. Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
In reply to the first and second questions: I think that the quoted paragraph is appropriate, because of four points:
  • Occam's razor indicates that if "cyclopentadienyl" is even partially systematically named, then it must be a radical.
  • References to unqualified "cyclopentadienyl" supports this interpretation.
  • Misinformation should be extinguished in Wikipedia.
  • The content of the initial version would not be lost, as it was a subset of another page: Cyclopentadienyl complex.
How do you suppose I am using "IUPAC nomenclature strictly" rather than being flexible? Please do go on. Plasmic Physics (talk) 02:21, 8 May 2014 (UTC)
Well, at least you are addressing the points made above. Your first two points however reinforces for me the point made above that you do not really understand chemistry. For any chemist, if the term "cyclopentadienyl" is used, he/she thinks of the anion. I do not understand your forth point. As far as the last point is concerned, I was just referring to the points made above. --Bduke (Discussion) 02:41, 8 May 2014 (UTC)
Please, all, stop with the "For any chemist" generalizations. Words have meaning in context. In an OM context, yes. In other contexts, not necessarily. In a formal setting such as an encyclopedia, not necessarily at all. Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
I did say unqualified Cp. My fourth point refers to how a similar version of the same content is present in the referred article. Seeing as how neither of us then recognizes the substance of the above accusations, perhaps then someone else can divulge. Plasmic Physics (talk) 03:08, 8 May 2014 (UTC)
  • Occam's razor .. in other words, you are arguing that the naming of pages on Wikipedia should follow IUPAC systematic nomenclature to the letter because everything else needs the assumption that there is an unreliable factor out there: what does the reader want? I'd like you to quote which part of the naming rules in any part of the MOS, or in any of our policies we use that as the argument for naming.
  • Practically all cases where Wikipedia is using 'cyclopentadienyl', it is about the anion (Cyclpentadienylthallium, etc.). Now you could argue that those are all to the qualified cyclopentadienyl, it is what Wikipedia by far talks the most about. If we have 50 articles with the word 'cyclopentadienyl' in the title, all talking about the anion, and then the editor who wants to know more about that is led to an article about the radical .. having to figure out through the dab that they has to be somewhere else, at cyclopentadienide, is, to say the least, confusing.
  • NO. The naming MOS made the specific choice that sometimes we do not follow the correct term, and if that is properly explained, that is not misinformation.
  • That last point has some truth to it .. although 'cyclopentadienyl' is not necessarily always talking about the complex, if you would have said 'cyclopentadienide or cyclopentadienide anion' that may have been an idea. But say that we have consensus to go to the systematic nomenclature, and we put 'cyclopentadienyl' at 'cyclopentadienide anion', and we make 'cyclopentadienyl' about the radical / functional group (difficult choice between the two, and they are really very closely related). In that case, we do not (gradually) change over the articles from one to another (confusing the edit history). What we do is we swap the titles through a move.
To me, one of the problems, Plasmic Phycics, is your interpretation and (way of) following of IUPAC systematic nomenclature. Moreover, your reasoning not to discuss is that it does not get to a consensus and hence that there is no need to discuss. And it is not the first time that you have been pointed to how you handle these situations, and that many editors on the chemistry wikiproject think, and seen you current restriction also some editors outside of that, that that behaviour has to change. Do you understand that it is, in the end, the same editing behaviour over and over that is resulting in editors having concerns over your edits? What would you suggest to do so that those concerns will not arise again? --Dirk Beetstra T C 04:14, 8 May 2014 (UTC)
That Wikipedia does anything consistently is the poorest of arguments for validity. Much content here is unsourced, and student-generated. Make claims based on verifiable sources, even here. While poorly fought, the anion v radical issue is a potentially valuable, content-clarifying matter. Resolve the core issue. Stop arguing about (i) the semantics, and (ii) the argument itself. PP, you as well. Bring it home. Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
Regarding your first point: no, I'm not arguing that at all, I'm explaining on why my interpretation is logical.
...Second point: by "unqualified cyclopentadienyl", I am referring to occurrences of the word cyclopentadienyl in isolation - not a segment of another systematic name, or an adjective.
...Third point: that is only true if you can justify with references that it is acceptable to figuratively call an apple an orange.
Often my reason for not discussing is the invocation of a discussion it is used to legitimize ignoring my query, and so prevent me from making any changes whatsoever. Another reason for not discussing, is because I do not think it necessary. Plasmic Physics (talk) 05:49, 8 May 2014 (UTC)
Whatever reason you might have for not discussing a substantial edit a priori, PP, it does not excuse you from the WP policies concerning consensus. Do you believe if you make a series of edits below radar (unseen for a time), such that reverting them is more difficult, that it will provide an alternative course to the WP required consensus? Clearly, this wall of discussion must persuade you that that strategy is a failed approach. No, there is no excuse for repeatedly trying to pull an "end around" the community, getting in edits that you believe, if discussed, would not result in consensus. Do the hard work of wikipedia; call on other chemistry editors such as me, and attend to the core chemistry issues. If this had been done, you would have been set back on your heels at times about use of IUPAC names, per se, but we likely would have (i) the anion and radical both appearing and differentiated (in same or different articles), and would have had (ii) a better, more accurate mechanism for carboxyl reactivity (cyclic TS, instead of errant UG ideas). Bottom line, you better start to see that your approach is neither proper nor productive, or the community will have its way. Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
1) I was not arguing that the interpretation was illogical.
2) Yes, I understand. And how much of the unqualified use of the term cyclopentadienyl do you see over the qualified (as anion) use of the term. Because MOS suggests to use the common use of the term.
3) Per 2, by far most of the information out there is using the term talking about the anion.
I know why you don't discuss, and that is another part of the problem. Your last sentence is even more concerning. --Dirk Beetstra T C 06:00, 8 May 2014 (UTC)
2) It is actually relatively rare to find a mention of unqualified "cyclopentadienyl". There are plenty of "Cp ligand", "Cp anion", "Cp cation", "Cp complex", and systematic names containing Cp, but rare ever just "cyclopentadienyl".
By my last sentence, I'm not saying that I never discuss, because of that reason; I'm saying that I occasionally don't discuss for that reason. Plasmic Physics (talk) 12:10, 9 May 2014 (UTC)
"It is actually relatively rare to find a mention of unqualified "cyclopentadienyl". So then we need to go by the qualified use, which is in most cases the anion or ligand .. and that is what the article was at.
And it is that not discussing when it is necessary what brings you here all the time. --Dirk Beetstra T C 04:15, 11 May 2014 (UTC)
Then the article should be renamed to a correct title. Me not discussing when it is necessary has been established in previous discussions, as has that "necessity" is a matter of perspective. Plasmic Physics (talk) 12:06, 11 May 2014 (UTC)
Perhaps now, finally, we are getting somewhere. Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
No, it should be at what is the most common use, not at what is correct according to the IUPAC nomenclature. --Dirk Beetstra T C 12:16, 11 May 2014 (UTC)
Alas back to square one. Dirk, no, a thousand times no. The term polyphenol—for non-polymeric substances, that, as oligomers of phenols of particular structures, give teas and berry jams their darker colour tones—has been highjacked, both in the web, and in poorer academic venues, in pursuit of the fact that true polyphenols have clear potential medical benefits. Does the Wikipedia article therefore simply take on the web-based mistaken attributions of commercial nutriceutcal suppliers or H-index pursuing scientists? No, this is fundamental mistake: failing to differentiate between lexicography (the tracking of the evolution of word meanings in common use) and scientific nomenclature (the establishment of technical meaning so that use of specific terms with such meanings remain defined and fixed over large tracks of time, so as to add convenience and precision to scientific discourse). If we mean Cp anion, say Cp anion. The hallway talk outside an OM lab is not formal chemical communication. For the last time, please: encyclopedic articles are formal venues of communication, and the two meanings of the term need to be disambiguated. There is fundamental validity to PP's point. Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
I've already showed how it is one of the least common uses. Plasmic Physics (talk) 12:19, 11 May 2014 (UTC)
Almost all, if not all, of the mentions of cyclopentadienyl on Wikipedia are to the qualified anion/ligand .. and that is where the public would encounter the word. The public does not know what that cyclopentadienyl stands for, and they should be directed to the correct article if they search in Google for cyclopentadienyl. Not to the radical, which is utterly confusing for the casual reader (even with a dab pointing to the anionic/ligand use of the term).
In any case, this changeover is contentious, obviously, and should have gone through discussion first, and, if consensus would be that way, not through a changeover but through a move of the articles. --Dirk Beetstra T C 12:25, 11 May 2014 (UTC)
Exactly, rarely if ever does Cyclopentadienyl implicitly refer to the anion, both on Wikipedia and on Google. If you are so adamant, find me three counter examples. Well, now I know that it is contentious. Plasmic Physics (talk) 12:36, 11 May 2014 (UTC)
────────────────────────────────────────────────────────────────────────────────────────────────────Oh for goodness sake: rarely if ever are people talking about the radical or the cationic form of cyclopentadienyl. They are rare. The only way you see the term is in the qualified form (but the non-chemist does not understand that, for them cyclopentadienyl is just a term, they do not know if it is the functional group there, the anion, the radical or the cation, they likely don't even know what it is; for a chemist, 'cyclopentadienyl sodium' is qualified as the anion, but the man in the street does not know that), and when they find that on Wikipedia, they should be on the page which explains them the term that is by far, far the most mentioned form: the anion. The article should then clearly state the things there (there are 'three other forms', some or all have their own article, etc. etc.).
In any case, rewriting such articles, especially when they are long-standing is not the way forward. That messes up the history of an article, or even of a set of articles. --Dirk Beetstra T C 03:40, 12 May 2014 (UTC)
That is why I agree with the prior suggestion of creating a disambiguation page. Plasmic Physics (talk) 04:27, 12 May 2014 (UTC)
No, you first changed the article over, then you agree with the creation of a disambiguation page. But do note that I still think that by far most of the times that the word 'cyclopentadienyl' is used somewhere, it is for the anion, and that hence cyclopentadienyl should be discussing the anion (or be a redirect to the more correct cyclopentadienide), and the article should be pointing to either the 3 other, way, way less common, possibilities of what the term may mean, or to cyclopentadienyl (disambiguation) .. but a discussion will either lead to that consensus, or we stay with the status quo that we have. --Dirk Beetstra T C 05:15, 12 May 2014 (UTC)
I was not stating happened, but what I prefer to occur. And I still think a thoroughly thunk through thought, which is that Cyclopentadienyl should be a redirect to Cyclopentadienyl (disambiguation), with three listed pages: Cyclopentadienyl complex, Cyclopentadienyl cation, Cyclopentadienyl anion, and Cyclopentadienyl radical. Since we're reaching a stale mate, at least a third vote is required. Plasmic Physics (talk) 07:49, 12 May 2014 (UTC)
On the acetic acid article, the edited statement needs a reference either way. The references on the paragraph do not actually talk about which part is more reactive. This is a featured article, so any statements need a reference. And in reality doesn't the hydrogen move between oxygen atoms anyway? Graeme Bartlett (talk) 22:16, 8 May 2014 (UTC)
Concur with referencing. The "which part is more reactive" prose is indicative of either fast composing (I'm guessing) or loose thinking. With ambient nucleophiles, bifunctional compounds (and which important substance we study is not that, or much more), etc., such words become near to meaningless. Yes, in Chem 1, we can say of an alkanal, that the aldehydic carbonyl is more reactive (than the remaining hydrocarbon chain). But, first, this is an encyclopedia (meaning we do not generalize to the point of losing accuracy of statement, rather we elaborate and qualify to remain accurate), and second, such simplifications are simply irrelevant to matters such as acid chloride formation, where both the carbonyl and acidic hydroxyl participate in perceived mechanisms of the reaction (again, see [7]!). Look at the modern protecting group-free chemistry work, for goodness sake; what is reactive depends entirely on the conditions into which the molecule is placed. I am guessing any of us can now find literature on a bifunctional organic that, under the correct conditions self-protects/masks, allowing chemistry to proceed on the least reactive functional group. Never lose sight of the reality, in simplifying explanations. Le PRof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
The alteration indented to indicate which part is attacked first. Yes, acetic acid does protomerically tautomerise, but both tautomers are degenerate, and in either case, the terminal oxygen is still the part which is attacked first, like a molecular game of keep-away. Plasmic Physics (talk) 12:10, 9 May 2014 (UTC)
I doubt that in free acetic acid you can even pinpoint in the initial state where the hydrogen is, and likely hydrogens are bound to both oxygens, and which of the two oxygens is doubly bonded is not extinguishable. --Dirk Beetstra T C 04:15, 11 May 2014 (UTC)
Once again, I point you to the Liverpool site ([8]), which is associate with the fine Clayden text. This discussion regarding "which part is attacked first" is utterly naive. As if the arrowed mechanisms drawn in first semester OChem reflect some hard, incontrovertible physical reality. Moreover, more generally the foregoing and following discussion is generally meaningless, generally nonsensical unless a specific context is stated clearly. Via many experimental methods, and at many experimental time scales, one "sees" no hydrogens at all—they are either moving too fast, or invisible to the technique. Stop arguing this, both sides. Outside of a specific block of article text, it is a waste of time. What is the point: What do both sides here want, and how can we achieve it? Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
That is not what spectroscopic studies reveal - the oxygen atoms are non-degenerate for carboxylic acids, which would be the case if the hydrogen atom was bridged between them. Plasmic Physics (talk) 12:06, 11 May 2014 (UTC)
.[citation needed] --Dirk Beetstra T C 12:16, 11 May 2014 (UTC)
It is a basic fact learnt in the first years of university. I'm sure if I tried I could find a reputable source, but for a lack of trying, our page on Carboxylic acids states it clearly. Plasmic Physics (talk) 12:26, 11 May 2014 (UTC)
Out of your league here PP. That a spectroscopic Pchem study can be found showing localization of a proton in a carboxylate system (what, at ultralow temperature? in crystal? in a 1,3-dione system?) is irrelevant to what is seen and studied in solutio, by practicing organic chemists, and these make up a significant portion of the audience you are writing for, and the fellow editors whose consensus you must reach. Here I am solidly on the side of the other voices. You simply are extrapolating from the wrong type of data to a generalization that is not valid. For goodness sake, hydrogen atoms tunnel; no scientist worth his salt stakes career on where a proton comes from in a mechanism, and few are doing the very careful mechanistic work to even to begin to approach such questions. Generally, mechanisms are a combination of inferences of reaction outcomes over a variety of systems, to which is applied "chemische Gefühl" (chemical intuition, the traditional approach), and now, selection among the inferred options based on solid computations (modern addition). Bottom line, arguing localization in simple, unconstrained organic structures, in solution at ambient temperatures and above (i.e., under conditions relevant to the chemistry of life, to pharmaceutical and other synthetic chemistry efforts, etc., etc.)—or arguing what part of a carboxylate is first to react—this is naivety beyond comprehension. Both sides, please, consider it a lost battle; this is so much embarassing balderdash. Sorry. Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
Please find a specific reliable reference Plasmic. If it is as you say then textbooks should say it. Wikipedia itself is not a reliable source for Wikipedia. Graeme Bartlett (talk) 21:34, 11 May 2014 (UTC)
Blackman et al, Allan (2008). Chemistry (1. publ. ed.). Milton, Queensland: John Wiley & Sons Australia. p. 789. ISBN 9-78047081-0866. . Plasmic Physics (talk) 23:38, 11 May 2014 (UTC)
It’s a long time since I was in chemistry—and I never got past “the first years”—but that agrees with my recollection. I can’t find an explicit statement to that effect in my old textbooks, but the following exercise question & answer would seem to support it: “[Q:] Why is resonance more important in the carboxylate ion than in the carboxyl group itself? [A:] Two equivalent resonance forms exist for the carboxylate ion.” (Allinger, Norman; et al. (1976). Organic Chemistry (2 ed.). New York: Worth Publishers, Inc. pp. 171, 962. ISBN 0-87901-050-9. ) ISTM that if the -COOH hydrogen were equally associated with both oxygens, the acid’s resonance structures, as well as the ion’s, would be equivalent.—Odysseus1479 00:07, 12 May 2014 (UTC)
And just think of the ring strain that a double association would impart. Plasmic Physics (talk) 00:51, 12 May 2014 (UTC)
Well, if the H were conceived as having half a bond with each O, one might expect such bonds to be extra-long (albeit not as long as an intermolecular H-bond), making for a less-strained configuration than that of e.g. cyclobutene.—Odysseus1479 02:22, 12 May 2014 (UTC)
On the other hand, I suppose a doubly associated form should exist as a transition state between tautomers. Plasmic Physics (talk) 04:43, 12 May 2014 (UTC)
Almost there, Plasmic Physics, I see you took the hint that I gave below. --Dirk Beetstra T C 05:15, 12 May 2014 (UTC)
Not so, by definition a transition state represents a non-existent configuration for a molecule that serves purely as a heuristic model of a reaction mechanism. Plasmic Physics (talk) 06:57, 12 May 2014 (UTC)
That is why I said you were almost there - it is not a transition state, and a transition state is a existent configuration (it has fleeting existence), though likely with a extremely short lifetime. --Dirk Beetstra T C 07:43, 13 May 2014 (UTC)
You confuse, the transition state for reactive intermediate. There was a reason that I Wiki-linked it. Plasmic Physics (talk) 11:49, 13 May 2014 (UTC)
You all are confusing, all talking past one another, and all tremendously off point. The question at hand, is whether PP is editing in such a manner as to require a block or ban. I have arrived at a qualified conclusion. The rest of this, apart from a specific context—carboxylic acid esterification under Fischer–Speier conditions, vibrational cryospectroscopy of formic acid, depsipeptide hydrolysis catalyzed by chymotrypsin—has little chance of being resolved here. Can we agree to leave this until we have an actual text that we are editing, and then, someone propose a sentence, in talk, in that particular context, so this discussion can conclude? Otherwise, you are also confusing time with a commodity that is in endless supply. Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
See where I take the term 'fleeting existence'. And that something can not be seen does not mean that it is a non-existent configuration. --Dirk Beetstra T C 05:28, 14 May 2014 (UTC)
By the definition of a transition state, it does mean exactly that. Plasmic Physics (talk) 08:03, 14 May 2014 (UTC)
When I look for that, the Google ebook only has under 400 pages, so cannot be verified. So can you quote a few words about that that says in your reference? Graeme Bartlett (talk) 08:54, 13 May 2014 (UTC)

The carboxyl group of a carboxylic acid gives rise to two characteristic absorptions in the infrared spectrum. One of these occurs in the region from 1700 to 1725 cm-1 and is associated with the stretching vibration of the carbonyl group. This region is essentially the same as that for the absorption of the carbonyl groups of aldehydes and ketones. The other infrared absorption characteristic of a carboxyl group is a peak between 2400 and 3400 cm-1 due to the stretching vibration of the O-H group.

It goes on to say that the difference in the spectrum between a single molecule and a dimer, is that the O-H peak is broadened for the dimer. Plasmic Physics (talk) 11:49, 13 May 2014 (UTC)
Thanks Plasmic. So it confirms what you said here, but not what the change or pre-change of the acetic acid article said about a group being more reactive, but instead that the groups are distinct. Graeme Bartlett (talk) 13:29, 13 May 2014 (UTC)
As I said, this is getting there. What is acetic acid (or any carboxylic acid) doing with their COOH groups in solution (or in the pure form) - hydrogen bond. Carboxylic acids do that even in the gas-phase when distilled. And that is why I was saying that this is all canonical thinking. Is what is represented in the mechanism what is really going on, or are the other molecules strongly involved (in exchange/bonding) while the reaction takes place.
Anyway, it diffuses from the fact, what is written there now is highly contentious, and the rewrite as well - point is that the statement should either be removed, OR properly referenced (all what we are doing at the moment is WP:OR!), or rewritten ánd properly referenced. --Dirk Beetstra T C 05:28, 14 May 2014 (UTC)
This is an example of why I'm insulted when others say that my understanding of chemistry is somehow more flawed that theirs. It may be true, but decency demand it to be justifiable if one dares to make such a public assertion. Plasmic Physics (talk) 00:57, 12 May 2014 (UTC)
I repeat my last point. Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
This is just what I expected. The problem is that this chemistry goes beyond the couple of first levels of high school, and may even surpass the first year of a chemistry degree. People discussing the situation of an isolated acetic acid molecule, Plasmic is even arguing that the ring strain for the 4-membered ring is a factor. Unfortunately, isolated acetic acid molecules are rather rare (even in gas phase), and here we are talking about liquid phase, where the 'hydrogen bonding' is intermolecular, not intramolecular (that of course still does not mean that one of the C-O bonds has more C=O character and the other C-O-H character - it is a matter of timescale).
Anyway, the majority of the reactions of acetic acid are due to its acidity, the formal removal of a proton from the C-O-H fragment. The example that is given in the sentence is a bad one (if one thinks strictly canonical), and in a way I think that whole sentence is bad and should just go. It is silly to discuss the reactivity of a COOH group in terms of the reactivity of the C=O vs. the C-O-H. They are chemically inseparable, indistinguishable in terms of reactivity, and thát is what should have been recognised by an experienced chemist. --Dirk Beetstra T C 03:40, 12 May 2014 (UTC)
As a practiced synthetic organic chemist, I disagree, thoroughly, to the attempts at simplified conclusions absent actual article context. For instance, it is simply too broad and simplistic a generalization to say "majority of the reactions of acetic acid are due to its acidity". Mon Dieu. mdr. HOAc is acidic because (and here I am falling prey to temptation, and moving too rapidly, and mixing thermodynamic and kinetic aspects of the question) the acidic proton is adjacent an electron deficient center (the carbonyl you marginalize!), and because, entropically, that carbonyl provides a second heteroatom onto which change can be delocalized. Again, this is all so much aimless, near pointless discussion. There are times when PP's point is more valid than not. What matters is the precise text (and pedagogic point), in context, and it does not pay to argue broad ideas and vagaries here. Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
You made an isolated molecule the topic. "The majority of the reactions of acetic acid are due to its acidity."[citation needed] We could go ad infinitum and debate whether or not they are degenerate, or we could we could replace the sentence with something that mentions types of structural analogues. Plasmic Physics (talk) 04:27, 12 May 2014 (UTC)
I used acetic acid as an example, the same is true for benzoic acid or whatever carboxylic acid.
That is what you should have been discussing from the beginning (or boldly change it to something more correct, not to something equally incorrect or even less correct - note that saying that the C=O is the reactive group that shows the reactivity with thionyl chloride is confusing: acetone does not undergo a similar reaction (with thionyl chloride, it needs something stronger and forms another type of compound), in ethanol the OH does get replaced with a chloride when reacted with thionyl chloride; and after the change we are discussing here it says that the C=O is more reactive in the COOH group .. ). --Dirk Beetstra T C 05:15, 12 May 2014 (UTC)
It may not be perfectly correct, but at least it the lesser of two evils. Oh, and I did initiate a discussion on the acetic acid talk page. There were no takers. Plasmic Physics (talk) 06:57, 12 May 2014 (UTC)
(edit conflict)I don’t know how you assess “the majority of the reactions” of a given substance—on the number of known reactions? the most mentioned in papers? the most commonly performed? Anyway, for another bit of dimly remembered trivia, radioactive labelling has shown that in the acid-catalysed dehydration of RCOOH with R'OH to form an ester, RCOOR', the water evolved gets its O from the acid, not the alcohol. In such reactions (nucleophilic substitution?) the mechanism begins with the protonation of the carbonyl oxygen and ends with its deprotonation. It would therefore seem hard to generalize about the relative reactivity of the carboxyl group’s components; it appears to depend a great deal on the reactants & other conditions.—Odysseus1479 07:18, 12 May 2014 (UTC)
The lesser of two evils - two wrongs don't make it right, Plasmic Physics. And no takers apparently means that there was no consensus to change either.
Regarding Odysseus1479's question, one could do a search of a scientific database of how many papers used reaction A vs. how many used reaction B. However, for a functional group which one could perceive as a combination of 2 functional groups (like here is done for the C=O and the C-O-H in -COOH) is probably impossible or even silly. --Dirk Beetstra T C 07:43, 13 May 2014 (UTC)
"No takers" means that everyone who had an interest in maintaining the article was apathetic at the time. Any consensus, or lack thereof, can only result from a dialogue. Disagreeing with my opinion that my change was less wrong than the original version is your prerogative, but that does make your opinion factual. Moreover, I gave you a fair chance to discuss the change before it was made; criticising my taking action according to my suggestion is not appropriate if you did not contribute to the decision. Plasmic Physics (talk) 11:49, 13 May 2014 (UTC)
Plasmic Physics, you are expecting that all discussion points are taken up in a reasonable time, and that consensus is reached on all of them. If an edit stands, then that edit has an apparent consensus, if then one editor challenges that, that may mean that consensus has changed, but if no-one responded to it, it does not mean that consensus has changed. If you make a bold-edit, and it gets reverted and discussed, but the discussion either bleeds to death or does not get any further participation, and no consensus is reached, then that does not mean that the bold-edit was right. And that seems to be a recurring theme with you. It even doesn't mean that if article A says '1' and article B says '2', that the non-consensus to change it from '1' to '2' in article A should result in a change from '2' to '1' in B (it may even be a WP:POINT violation to do so). --Dirk Beetstra T C 05:28, 14 May 2014 (UTC)
Yes, I'm expecting that all discussion points are taken up in a reasonable time, because that is what I'm advised by the Wikipedia guidelines. If an editor challenges an edit which was uncontested following a reasonable amount of time, responsibility falls on that editor to open a new discussion before boldly reverting the edit. The edit was not bold, since it was discussed on the talk-page. Plasmic Physics (talk) 08:03, 14 May 2014 (UTC)
I encourage you to read WP:CYCLE. This will help you develop a better understanding of the bold-revert-discuss process. Plasmic Physics (talk) 08:17, 14 May 2014 (UTC)
'[R]easonable time' is very subjective, anyway, a stale discussion or a discussion that does not move to consensus can be pulled forward with a (bold) edit, but that does not mean that that edit has automatically consensus because the discussion died out, it can still be reverted (with reason) and either consensus needs to be reached, or the edit really does not have consensus and should simply not be performed, or something else could be tried.
WP:BRD was exactly what I had in mind: bold edits can come after a discussion died out, or when the discussion did not get to consensus. Anyway, my first reverts for both articles (acid and Cp) were reasoned. And what you say conflates the issue - one was an undiscussed bold edit, the other was a bold edit which was first discussed, but not gotten to the final. Both were reverted because someone disagreed (I reverted, Smokefoot already gave his concerns before) . That means that discussion goes on, and not that the bold edit has to go again, even after the second cycle of discussion has died out. The issue seems however to be that you do a lot of bold edits which do not have consensus. --Dirk Beetstra T C 09:13, 14 May 2014 (UTC)
In that case, I shall direct your attention to "BRD is not a valid excuse for reverting good-faith efforts to improve a page simply because you don't like the changes." Plasmic Physics (talk) 10:18, 14 May 2014 (UTC)
I did not revert because I don't like it, I reverted because I don't think that they improve Wikipedia, and I certainly think that this needs more discussion and, possibly, another solution. --Dirk Beetstra T C 11:15, 14 May 2014 (UTC)
It comes down to the same thing, disapproving of/disagreeing with an attempt to improve a page. Plasmic Physics (talk) 12:31, 14 May 2014 (UTC)

Unless someone has anything else to add, Q.E.D. Plasmic Physics (talk) 03:45, 19 May 2014 (UTC)

Here we go again with Plasmic Physics - part 2[edit]

Plasmic Physics appears to have changed the total focus of Titanium hydride back in October 1st, 2012. Another user is now trying to change it back. The original change was not discussed at Talk:Titanium hydride or in edit summaries. Please take a look at his comment on my talk page, the history of this article and the recent discussion at Talk:Titanium hydride. I am rather busy to get too involved. --Bduke (Discussion) 03:37, 25 May 2014 (UTC)

This foregoing, in its closing, appears to have accomplished nothing it seems, so I will close with a formal proposal:
* (i) that all cosignatories consciously return to the principles of WP with respect to these chemistry discussions, including AGF and other policies requiring mutual respect in actions and discussion;
* (ii) that PP and all cosignatories herecommit unequivocally to add no substantial chemistry text material without good secondary / tertiary scientific sources—not primary sources, and with sources substantially beyond UG first and second year texts (graduate texts, reviews, and monographs preferred);
* (iii) that in selection of chemistry citations, proof-texting be avoided, and instead, a commitment be made to identifying the preponderance of scientific opinion—not via Google, but through reliable scientific search venues such as CAS SciFinder, Pubmed, Thomson Reuters Web of Science, etc.;
* (iv) that by all cosignatories, the difference between nomenclature and lexicography discussed above be acknowledged, and through the use of disambiguation, and careful name choice, both familiar and unfamiliar chemical concepts be given adequate definition and coverage in article images and text (whether in same or different articles);
* (v) that PP agree to make no gross change to article nomenclature without creating a talk page, prior, and laying out the reasons for the overarching change, and that Talk section be allowed to stand for two weeks before a bold, comprehensive nomenclature edit is made;
* (vi) that for any article for which PP can reasonably be aware that the cosignatories of this long discussion have interest or past involvement, that the same "discuss first" rule be again adhered to for any major edit, or series of minor edits that taken together constitute a significant change to the article text (given the clear differences of opinion about approach to practical editing that this page lays bare); in such cases, the same let Talk stand for two weeks criteria be applied;
* (vii) that on becoming aware of the indicated Talk sections, that the cosignatories of the foregoing long discussions agree to approach matters civilly, with both sides committed to the careful thorough conversation as eventually was seen in the foregoing discussion;
* (viii) that when a no point of consensus is soon reached in these Talk venues, all cosignatories here agree to seek additional participants to weigh both sides of the issue, in the specific context (and I will volunteer evening time for this if I am available); all then agree to abide by the consensus that is eventually reached (e.g., and if in the minority, not return again after a pause, to attempt to subvert consensus);
* (ix) that all cosignatories here agree, whether for edits covered above or otherwise, that on experience of first reversion of an edit, to move the matter immediately to Talk, and allow the initial, more longstanding text to remain in place, while discussion takes place over the aim of the once-reverted edits (where points vii and viii again apply); and
* (x) that all take seriously their own intellectual limitations, and respect the need for stable article spaces, and accept that return to earlier business-as-usual approaches to get edits in place may result in a block of work in this Project.
Bottom line: Can we not overly dissect, this, but instead, all agree to abide by it? I have heart remaining for about ten more minutes of this, and then, no more. Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
Well Leprof 7272 you have certainly made a big effort to respond to many of the points raised. Our discussion did stray off the initially raised topic and into a couple of specific changes made by PP. And some of that discussion should take place on the article talk pages. Some of us have a problem with (ii), but I agree if there is a dispute about a fact then we should consult the good non-primary sources. But I support your points i and iii-x. Graeme Bartlett (talk) 21:29, 29 May 2014 (UTC)
Graeme, ty for replying, and perhaps be prepared to reword (ii), as is necessary, to make it more broadly acceptable. Le Prof Leprof 7272 (talk) 05:38, 1 June 2014 (UTC)
Although I do not agree with the interpretation of my remarks (but that may be in my wording; I am not responding to the points individually, how vehemently I disagree with how Leprof 7272 interpreted them - I think we basically agree, Leprof 7272), I do think that what User:Leprof 7272 has been suggesting is basically what we all would expect from editors in the first place. --Dirk Beetstra T C 03:47, 1 June 2014 (UTC)
I think we do and will agree quite more than you might think DB. But, ignoring the chem matters (which can be settled at actual articles)—it seems you are agreeing with the thrust of the proposal? If so, and if PP does not respond, I will leave it to you how to take this forward. My view is that if something is not formalised as a result of this discussion, first here, and if necessary at an administrative board, then the behaviour and argument will recur (see Bduke above, re TiH2). This will create further confusion and waste further time in article editing, and will eventually result in lost tempers and emotion-fueled bans/blocks against PP (as almost happened here), that will just set up conflict long-term. The proposal wording was carefully chosen, as you and Graeme both surmise, to make the point that what is being asked is what all should be able to agree to, generally. And with respect to past issues with PP, it is solid enough [see (v) and (vi)], that if it is flouted, it can then be taken immediately back to Admins, for the block or ban originally requested. The only grant being really asked of you is implied in (iv), and that is that the -yl radical find a home somewhere—but the details of this can and should be left for later, to the actual articles and talk pages, where you can still fight to see your important perspectives heard. Bottom line, can the foregoing be asked of PP, to forestall another round of this, if he seeks at some point to redirect articles without consensus? Cheers. Le Prof Leprof 7272 (talk) 05:38, 1 June 2014 (UTC)
Long proposals such as the text at 20:10, 29 May 2014 above are generally unsatisfactory at Wikipedia because there are too many details to argue about, and because an uninvolved admin would have a great deal of trouble determining whether a particular clause had been breached (bearing in mind WP:AGF and WP:BOLD). The actual problem is that one editor is not working collaboratively and is causing disruption, and experience from other cases shows that ongoing problems may still occur even if all clauses in the proposal are followed. This project does not have the power to sanction an editor, and unless clear evidence that is understandable by third parties is available, an admin noticeboard is unlikely to help. If no rogue admin is available (John—do you want a challenge?), an WP:RFC/U may be necessary. If good evidence and discussion occurs in an RFC, with a solid consensus that there is a problem, any ongoing problems would be likely to result in a topic ban at an admin noticeboard. That would involve a lot more time wasting I'm afraid. Johnuniq (talk) 06:55, 1 June 2014 (UTC)
@Leprof 7272: - the thrust of the proposal is basically what the policies and guidelines of Wikipedia suggest, and what has been suggested over and over. It has however been bringing us here with Plasmic Physics on a regular basis. What brings us here were not the 2 specific cases, what brings us here is how Plasmic Physics was solving the, real, situations that 'cyclopentadienyl' and 'the COOH-functionality' represented (and similarly, titanium hydride and mercury hydride, and earlier situations with categorisation of alkenes and naming conventions). I don't disagree that there are issues as things were standing (he does correctly 'attack' problematic cases), I don't disagree that there are solutions or whether things should be covered (we do need to cover the cyclopentadienyl radical), the basic issue is how solutions are implemented, and which solution is implemented [by Plasmic Physics] - that, again and again, is bringing the controversy here. --Dirk Beetstra T C 07:41, 1 June 2014 (UTC)

I can agree to proposals i to x, except for ii and vi. My reasons: while ideal, it is not possible in all cases, e.g. for some articles there simply do not exist secondary sources; it is rarely if ever known which articles are covered by vi, moreover, this is complicated by WP:HOUNDING. Plasmic Physics (talk) 07:39, 1 June 2014 (UTC)

  • I can have a look. What do you guys see as the problem? What do you all see as a workable realistic outcome from this? --John (talk) 10:43, 1 June 2014 (UTC)
    • @John: - the problem is quite convoluted. One of the problems is the total change-over of long-standing articles (changing subject; see cyclopentadienyl, titanium hydride, mercury hydride) without prior discussion (or, if discussion was initiated and dies out, boldly implementing a solution where there is maybe no opposition, but also no support for overturning the current version). But naming conventions etc. are also part of the issue (part of a currently active restriction on Plasmic Physics), as is sometimes a too 'canonical' way of thinking (putting aromatics in cycloalkene categories, -COOH-group discussion above). --Dirk Beetstra T C 12:09, 1 June 2014 (UTC)
      • I see. Yes, I read some of the discussions and the -COOH discussion was interesting. If I get involved here, do you think you need an experienced editor's opinion, or admin action? I can do either. --John (talk) 17:39, 1 June 2014 (UTC)
John, at this stage, I think what is needed, is Admin guidance, if not action, see following.
The fact that PP will not agree to point (ii) for the reason stated, is not an issue. Of course, if a bit of text is not yet supported by monographs or reviews, yet reflects the preponderance of scientific opinion—e.g., as seen by its appearing repeatedly in primary source article introductions—it is certainly acceptable; what is prohibited for WP editors is our determining from a primary source or the data whether something is true or not, our determining from these what is important or not. (The Flippin-Lodge angle concept appeared for years only in primary sources citing the original Clayton Heathcock articles, apart from a single Aldrichimica Acta review; but the concept was broadly recognized through all of these primary article citations as an accepted concept (long before the book sections and chapters began to appear). So on this point, PP, cheers, fine.
However, here is the rub, as I see it. PP is not always wrong about the chemistry (though he sometimes is, in emphasis or fact, as we all are). He has, however, shown a pattern of practices that seem to be attempts at end-arounds of community perspective—knowing from past discussion that his edits will not achieve consensus, but doing them anyway, or worse, as Dirk notes, "if discussion was initiated and dies out, boldly implementing [his] solution…" (despite the fact that the discussion did not yield that consensus). It was for this reason I proposed points (v) and (vi), above.
It seems that PP is willing to assent to (v), about not commandeering articles to institute broad changes in keeping with his singular perspectives on nomenclature. He appears unwilling, however, to assent to (vi), that is, to try to anticipate possible occasions of community opposition, despite the clear patterns of conflict in his interactions here with other chem editors. His excuses for not being willing, as (vi) asks, to pre-post at Talk at articles where he anticipates there might be opposition, are:
  • How can I possibly know? Ans., check Talk for familiar opponents, something that takes all of 60 secs., and then consult your prior experience—e.g., knowing that a further foray into metal hydrides, or aromatics as cycloalkenes, or common OChem functional group analysis from a PChem perspective are very likely to cause problems.
  • I say no, because to say yes is to allow my being hounded. Ans. It is not hounding for experienced editors to keep tabs on specific other editors who have displayed a pattern of naive, or otherwise problematic edits, or other behaviour which is problematic at Wikipedia. (I have several who do this with my every edit, hoping to show up Le Prof. It is their freedom. I just laugh.)
Bottom line for me, first, PP's continuing unwillingness to agree to reasonable restraints on his behaviour is problematic, and suggests the issues and conflicts will continue to occur. Second, many of his perspectives, from this professional chemist's perspective, are decidedly naive. If three others concur that we are arguing against a naive opinion, we cannot be expected to individually take this or any editor from an undergraduate perspective to a depth of understanding gained from further decades of teaching or research. No, if a consensus about article content exists, the argument is over, even if it is against him. What we have to expect from him, esp. given the further disciplinary consensus that appears here as to the problems he causes, is that he bring a greater modicum of humility to his editing, allowing that he does not have the right to redirect entire articles based on a hunch that he understands it better than the rest of the community, or that his way of expressing a subject should be what appears. Even if his confidence did not considerably outpace his real understanding, he could not expect to subvert consensus, expressed or anticipated.
Because he is unwilling to accept the need to work toward consensus, I now propose he limit his editing to nanotechnology, and not to any area of general, organic, inorganic, organometallic, or other chemical specialty (for which he has even more limited experience than his major coursework). I did not come in to this, in favor of any restriction on his editing, but now I am. Le Prof Leprof 7272 (talk) 22:35, 1 June 2014 (UTC)
You misunderstand, many articles to which I have made problematic edits, only gains interest or attention as a result of hounding. I can agree to vi, when issues pertaining to it has been resolved. Progress has been made, in that a category of article types has been established. Plasmic Physics (talk) 00:08, 2 June 2014 (UTC)
"hounding" ? Please explain what you mean. I see no hounding. --Bduke (Discussion) 00:54, 2 June 2014 (UTC)
"Wikihounding is the singling out of one or more editors, and joining discussions on multiple pages or topics they may edit or multiple debates where they contribute, in order to repeatedly confront or inhibit their work. This is with an apparent aim of creating irritation, annoyance or distress to the other editor. Wikihounding usually involves following the target from place to place on Wikipedia." The main belligerent is Smokefoot, I suspect there may be others, however they are not so wholly committed and so are the more difficult to identify. Plasmic Physics (talk) 01:04, 2 June 2014 (UTC)
What nonsense. Smokefoot is doing nothing of the kind. It is you who are irritating a lot of editors of chemistry articles and not learning from the criticism that comes from several editors. I am beginning to agree with Le prof.--Bduke (Discussion) 02:54, 2 June 2014 (UTC)
PP, first, it is entirely feasible for you to accept point (vi), without further argument. You need just [a] check the Talk page in new articles that you intend to edit, for the interest of others who have been critical of your history of chemical editing, and [b] when beginning to edit at such a page in their spheres of influx, post a prior Talk page explaining what you intend. That is, plan for, think about, and communicate what you intend to edit, before you act. See for instance: [9], and Talk sections thereafter. At this page, I have had contentious relations with a fellow editor, and so I pre-post every edit I intend to make, so if he should so care, he can pipe in and argue it. I am not asking anything of you that I myself do not do in similar situations. Now, will you or will you not accept this guidance?
Second, your arguing the hounding matter needs to cease. If and when someone "hounds" you in future, create a clear, recent, substantial record of it, and take it to the Admin pages. There, cite the specific part of the WP policies you think are being violated. Your arguments here, communicating your recollections of policies—they will not reverse the fact that the consensus here is that no one is hounding you. Accept this consensus, stop wasting time (or pursue the separate formal complaint, elsewhere). Your rejection of (vi) for reasons of what are, at best, a loose, and informally leveled counter-accusation simply is immaterial here. Will you or will you not accept constraints (v) and (vi) going forward? The alternative: next hint of an issue, I will stop defending you—for reasons of due process, or otherwise—and will join the call for your being formally limited in your editing. Le Prof Leprof 7272 (talk) 03:22, 2 June 2014 (UTC)
Indeed, the hounding accusation is nonsense. IF (and I say if) someone is following you around checking your edits, then the sole reason for that is that it is needed, because every time your edits are being discussed it turns out that what you were doing is, at least, controversial (and when looking back often other edits show up that turn out to be controversial (the Titanium hydride changeover was noticed 1 1/2 year after the fact - if it was hounding, those would have come out immediately). It might be hounding if the editors would report you for non-issues. --Dirk Beetstra T C 03:30, 2 June 2014 (UTC)
To validate me accepting vi, please give case where vi would retrospectively apply, where there has been previous invested interest by another user of the project. Why do I need to cease arguing the hounding matter? I don't care enough to bring it to the Admin pages. How can anyone justifiably decide whether I've been hounded or not, without so much as a shred of evidence either for or against? Regardless, a verdict does not help in solving the issue of handling cases where interest in an edited article has been gained for the wrong reasons, frustrating vi. Plasmic Physics (talk) 04:51, 2 June 2014 (UTC)
Do you understand that targeting me personally with clause vi, is akin to accusing me of not having abided up to now? That is why I take issue, and require justification. Plasmic Physics (talk) 04:55, 2 June 2014 (UTC)
Plasmic Physics, this is not a court of law and we will gain nothing in talking about hounding. If there's a consensus here that your editing should be limited, then arguably that would be binding. Do you see any down side in accepting the proposal that your edits here should be bound by consensus, the same rule we should all be following anyway? --John (talk) 23:47, 2 June 2014 (UTC)
I totally agree, I'm not interested in discussing hounding, but instead how to take its supposed existence into consideration when negotiating clause vi. No, I don't see any downside to being bound by consensus. Plasmic Physics (talk) 02:35, 3 June 2014 (UTC)
OK, thanks for that. I don't see any obstacle to agreeing the principles at the top of this. Are you worried people will use them against you? If you sign up, I will make sure that doesn't happen. I can tell you are an intelligent and well-meaning editor but it sometimes happens that intelligent and well-meaning people disagree. It looks like you have disagreed with a whole lot of people here. If you sign up to something voluntarily it will be a lot smoother and easier than if we have to go through the palaver of having a wider community discussion at one of the boards. It's up to you of course. --John (talk) 07:00, 3 June 2014 (UTC)
Fine, I suppose we can postpone resolution of the issues which I have raised, to a later date. After all, the proposal is not set in concrete. I don't take to shooting first and asking questions later, hence my reluctance. That said, I agree to attempt a strict adherence to clauses i, iii-v, and vii-x contained within the above proposal; and where possible, to clauses ii, vi; subject to future consideration and amendment. Plasmic Physics (talk) 09:31, 3 June 2014 (UTC)
I would also like to have an xith clause added, that calls for a restoration of civility - that disgruntled users not make a mountain out of a molehill by automatically raising every single issue before the Project, before attempting a BRD cycle. Plasmic Physics (talk) 09:40, 3 June 2014 (UTC)
It would be appreciated if someone would acknowledge with a response. Plasmic Physics (talk) 12:17, 4 June 2014 (UTC)
I acknowledge your response, and I appreciate it to some degree, but I am a little perplexed. If I understood correctly, the terms you have agreed to alter the normal "BRD cycle" in your case. I think therefore your previous response is difficult to parse. I certainly agree that people ought to be civil. Do you think anyone has been uncivil to you? --John (talk) 15:28, 4 June 2014 (UTC)
How do you suppose my terms alter the cycle? Yes, I think someone has been uncivil, but who that is, is besides the point. Plasmic Physics (talk) 22:39, 4 June 2014 (UTC)
Because some of the terms you have agreed modify or extend the normal editing cycle. (v) that PP agree to make no gross change to article nomenclature without creating a talk page, prior, and laying out the reasons for the overarching change, and that Talk section be allowed to stand for two weeks before a bold, comprehensive nomenclature edit is made for example, is not a usual requirement for editing. I think it is for the good though, and I will help make sure that nobody is uncivil or gives the impression they are hounding you, if you unequivocally accept them. Do you? --John (talk) 20:42, 5 June 2014 (UTC)

Proposed solution[edit]

I'll summarise the proposal as I see it more succinctly. User:Plasmic Physics will seek consensus using high quality sources before making any changes to chemistry-related articles which might be seen as controversial. If in doubt, assume it is controversial. I will enforce this with warnings and blocks if necessary. I will also mentor PP and suggest ways that he can edit more productively. I will also enforce the highest level of politeness and collegiality in other editors dealing with PP. This too I will enforce with warnings and blocks if necessary. My aim going into this would be to enable harmonious and productive editing from all involved and to keep admin action to an absolute minimum. Full disclosure: I am a Chemistry graduate and educator with many years' experience. I recently worked with others, especially User:Sandbh, to get our metalloid article to FA class. I do not think this degree of involvement rules me out from making this offer. If anybody does, please feel free to state it and I will consider withdrawing. Please indicate below if you accept this. --John (talk) 21:06, 5 June 2014 (UTC)



  • Ok, with no objections and plenty of sign ups I will take this on as described above. Please, anyone who sees anything they think I may have missed, just ping me. --John (talk) 23:26, 20 June 2014 (UTC)

Extraction of carbon dioxide from seawater[edit]

Dear chemistry experts: After watching this video I looked to see what Wikipedia had to say on this topic, and couldn't find anything. There are plenty of news, journal, and other reports about this (THESE, for example). Is there already information somewhere on Wikipedia about this topic, and, if not, would it be appropriate to start an article about it? —Anne Delong (talk) 14:38, 12 May 2014 (UTC)

Have a look at Carbon dioxide removal, and Carbon sequestration. I suggest adding to one of those articles. Plasmic Physics (talk) 23:23, 12 May 2014 (UTC)
Those articles are concerned with long term storage of carbon as a method of mitigating climate change. The topic I am suggesting is the opposite; retrieving it as a first step in the on-site creation of synthetic fuel. Examples could be providing fuel on a remote island, or synthesizing fuel on an aircraft carrier. —Anne Delong (talk) 10:15, 13 May 2014 (UTC)
In that case, try Synthetic fuel. See this link, it is not about fuel from seawater, but it is related. Plasmic Physics (talk) 11:56, 13 May 2014 (UTC)
  • Bit complex this. For the most part CO2 exists in seawater as a range of dissolved carbonates. The partial electrolysis of water gives H2 and H+ (and some O2 no doubt). The H+ liberates the CO2 and I'm guessing that goes into a reverse water gas shift to give you some CO. CO and H2 then feed into a Fischer–Tropsch process to produce fuel. None of these steps is novel but joining them all together without the result being hugely inefficient is quite an achievement. Project Osprey (talk) 20:26, 14 May 2014 (UTC)
  • I agree, and this is what caught my interest, since the references seem to indicate that this could be done at a cost that was not too prohibitive. I thought someone at this project might like to write it up. Dim memories of my high school chemistry classes in the '60's have left me unprepared to do it myself. —Anne Delong (talk) 04:00, 25 May 2014 (UTC)
Will also look into it Anne. Good to "see" you as always. Le Prof Leprof 7272 (talk) 06:12, 1 June 2014 (UTC)

Leaflet For Wikiproject Chemistry At Wikimania 2014[edit]

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Adikhajuria (talk) 11:33, 25 May 2014 (UTC)

Nondescript name vis-a-vis steeochemistry, yet stereodefined structures in box, etc.[edit]

General and specific questions here—how to fix the morass of conflicting information about compound identity and structure at this site, [10]. Expert replies requested (knowledgeable about clear stereo/structure issues, but also about Wiki standards for stereo-nondescript names, and structures that should appear). Le Prof Leprof 7272 (talk) 02:46, 2 June 2014 (UTC)

Opening discussion on future course of Natural Product article, [11][edit]


Fluorescein atropisomerism ?[edit]


question with no respons on fr:Discussion_Projet:Chimie#atropoisomérie_de_la_fluorescéine_?
I see this image with mark of atropisomerism on Fluorescein isothiocyanate and I found only this abstract which seems to proove the fluorescein atropisomerism. I search for other refs to put a section stereochemistry on the articles like Fluorescein and derivated (eosins, rhodamines, etc.) but for the moment I don't find anyone= HELP ! --Titou (talk) 12:14, 3 June 2014 (UTC)

Its been used for fluorescence anisotropy binding studies - so yes, it must have restricted rotation. That's quite a complex example though, I'll see if I can find something a bit more general.Project Osprey (talk) 13:40, 3 June 2014 (UTC)
  • Actually, strike that, this is more complex than it first looked... it has restricted rotation, but not atropisomerism. The benzene can't rotate, but that doesn't matter because the hydroxy-xanthenone can rapidly tautomerise. It also seems to have a lactone form (cas: 3326-32-7), I've added an image of the corresponding fluorescein to give you an idea, but I can't find an authoritative source on how easy it is to switch between isomers. Project Osprey (talk) 15:42, 3 June 2014 (UTC)
Various conditions make certain fluoresceins more or less stable one way or another (substituents on the rings, intramolecular H-bonding, etc.), and altering the conditions can trigger a switch. See for example: doi:10.1039/C1OB05387F, PMID 17471452, doi:10.1021/ja01404a016, doi:10.1016/S0927-7757(99)00313-1. I don't know the kinetics of the switch, or especially whether there is rapid equilibrium with just a possibly strongly favored direction vs a fairly stable state that can be caused to make a non-reversing/one-way-reaction change to the other. DMacks (talk) 17:55, 3 June 2014 (UTC)
Okay. So it's may be only the Fluorescein isothiocyanate which have atropoisomer like the molecule in the abstract? or we must modify the picture which would be wrong --Titou (talk) 13:02, 6 June 2014 (UTC)
I think that all of these fluroecein derivatives can show atropisomerism if they have the lactone that can be opened by keto-enol tautomerism as it is the ring-opened forms that are atropisomers. --The chemistds (talk) 13:09, 6 June 2014 (UTC)
All good discussion, but someone might mention to the posting editor, @Titou, that none of this matters to WP if a good secondary source on the matter cannot be found. The ACS abstract presented in no way can be considered a suitable source to make such a claim here. Or have I missed a link-out to a good source, here? (There is evidence that Applied Biosystems had IP in this, beginning in the early 2000s, likely through acquisition, but I have no wish to fuel a conversation that cannot come to productive fruition.) Bottom line, not even the beginnings of a "proove" here — simply not ready for prime time. Cheers. Le Prof Leprof 7272 (talk) 05:54, 9 June 2014 (UTC)
Okay, then corrects, please, this picture since the mark of atropoisomerism have no source and it seems out of question to discuss if there isn't good secondary sources ! --Titou (talk) 13:11, 15 June 2014 (UTC)

Wikipedia talk:Articles for creation/Guinier-Preston zone[edit]

Dear chemistry experts: I am not sure if this abandoned draft is about a chemistry topic, or if there is a better place to report it. Is this a notable topic, and should the page be kept instead of being deleted as a stale draft? —Anne Delong (talk) 05:59, 7 June 2014 (UTC)

I accepted it. Graeme Bartlett (talk) 21:24, 12 June 2014 (UTC)
Great! —Anne Delong (talk) 13:36, 25 June 2014 (UTC)

Wikipedia talk:Articles for creation/Indium-mediated allylations[edit]

Hello, chemists - one more of those abandoned AfC submissions. Is this a notable chemistry topic? Should the page be kept and improved instead of being deleted as a stale draft? —Anne Delong (talk) 14:05, 8 June 2014 (UTC)

  • Thanks for finding that. Since both were written by the same single author, the draft wasn't needed, so I have deleted it. —Anne Delong (talk) 04:22, 11 June 2014 (UTC)

Wrong category name?[edit]

Please express your opinion here. --Daniele Pugliesi (talk) 02:23, 9 June 2014 (UTC)

AfC submission - 10/06[edit]

Draft:Chemistry of Adhesive Tapes. FoCuSandLeArN (talk) 00:42, 11 June 2014 (UTC) There is NO "chemistry of adhesive tapes". There is chemistry of adhesives. And there is the fabrication of adhesive tapes, sort of an engineering thing. Otherwise we are going to get a whole series of articles on "Chemistry of [your topic here]. The article should have been integrated into adhesive tape and pressure-sensitive adhesives. Anne, can you induce those blendings, because the two enhanced articles would be stronger than these three self-standing things. A problem (and a strength, in some cases) with Wikipedia is that anyone can create an article, it is more challenging to integrate. --Smokefoot (talk) 12:06, 12 June 2014 (UTC)

Schoolwork review needed[edit]

A class project has recently added a lot of content to preservative. I have found it to be riddled with errors and biases. I have started cleaning up and correcting some of it, but if other chemists could take a look at it, that would be helpful. ChemNerd (talk) 11:39, 14 June 2014 (UTC)

Questionable category[edit]

I've found a newly created category that does not have a well-defined candidate definition, and furthermore, its usefulness is not evident. Category:Bulk chemicals. Perhaps, it is a CFD? Plasmic Physics (talk) 09:13, 17 June 2014 (UTC)

"Bulk" is certainly vague, but I don't see a problem with the concept of categorizing chemicals which have high commercial use. Maybe the category could be defined (and/or renamed) along the lines of High production volume chemicals which has an unambiguous definition. -- Ed (Edgar181) 12:48, 17 June 2014 (UTC)
I think commodity chemicals is a less-vague synonym for bulk chemicals. Antony–22 (talkcontribs) 17:49, 17 June 2014 (UTC)
While no disagreement with Antony, to PP I say, forget the IUPAC rigour here: the term has a widely/generally understood meaning. Edgar is correct, but commodity is no less vague, and both are rooted in history of practice. Whether it can be improved or better defined should be the bailiwick of industrial chem experts here, not fly-bys (and not discovery chemists like me, or students or physical chemists). This old chemists opinion. See here for definitions, [14]. Cheers, and hope all is otherwise well, your mate, Le Prof Leprof 7272 (talk) 05:15, 21 June 2014 (UTC)
Apart from its validity in commerce, where safe transport is the issue, it has a further regulatory niche in storage:

"Regulated Chemical Bulk Storage tanks are defined as (6NYCRR Part 596): (i) an aboveground tank storing a hazardous substance, or mixture thereof, with a capacity of one-hundred and eighty-five (185) gallons or greater; (ii) an underground tank storing a hazardous substance or mixture thereof of any capacity; or (iii) a non-stationary tank used to store one thousand (1,000) kilograms (2,200 lbs.) or more of a hazardous substance or mixture thereof for a period of ninety (90) consecutive days or more.​​​​​​​​​​​​​" [See [15]]

You see, after 20-30 years doing something, you can begin to trust instincts. Until then, mate, do the research before acting/suggesting. (You could have found this as well as I.) Le Prof Leprof 7272 (talk) 05:34, 21 June 2014 (UTC)
Honestly, what are you talking about? I came here for a second opinion, as is appropriate. Plasmic Physics (talk) 06:06, 21 June 2014 (UTC)
Answered at the appropriate User Talk page. Le Prof Leprof 7272 (talk) 00:14, 22 July 2014 (UTC)

Wiki Interactive Periodic Table needs to be consistent with standard periodic table.[edit]

The content of is okay.

What does need changing is the format of the interactive periodic table that Wiki shows for each element. For all the elements this non-standard and unusual periodic table shows at the top right corner. For example Carbon:

Why have Wiki programmers not used a periodic table format that looks like either of the first two periodic tables listed at ? This format is self-consistent with IUPAC, NIST, etc.

IUPAC Periodic Table. National Institute of Standards and Technology, Periodic Table.

Using a non-standard periodic table is misleading and the interactive periodic table shown on Wiki for each element is incorrect.

Historical discussion of alternative, proposed, and (now considered) incorrect periodic tables is fine. But using a non-standard periodic table format for all the individual elements is not.

Wiki needs to display the commonly accepted format for the interactive periodic table shown for each element: It is the same as shown in the first two images at — Preceding unsigned comment added by (talk) 23:11, 18 June 2014 (UTC)

It's not incorrect: it just puts the lanthanides and actinides in the main body of the periodic table, which is where they should go according to the asterisks in the main periodic table. I guess it could be a bit confusing without the element symbols, but it is equivalent to the 18-column periodic table.
The 18-column format is widely used mostly due to space limitations on paper, but I wouldn't mind changing it to that for the purpose of recognizability (the cells would have to be slightly bigger to preserve the width, but it would become easier to click on a particular element). With the symbols included, like in the periodic table footer on each element, I think there is no problem with using a 32-column periodic table.
Nevertheless the 18-column periodic table might be a bit confusing without the symbols: you don't know then if the convention being used is to put lanthanum or lutetium below yttrium, or none of them. With the 32-column table, you can tell between these alternatives by checking if the d-block is broken. Double sharp (talk) 02:38, 19 June 2014 (UTC)

You just single-handedly decided to ignore IUPAC, NIST, and over 100 years of periodic table history.

The placement of lanthanum (and later on actinium) under scandium and yttrium in group 3 (IIIB) has been the standard for many years; for example, the first edition of the CRC Handbook of Chemistry and Physics published 1913, page 70 titled, “Periodic Arrangement of the Elements – Mendelejeffs (Revised to 1911)” (1), and the Handbook of Chemistry published 1946 (2). This placement continues to be the standard; for example, the CRC Handbook of Chemistry and Physics (which I have access to many editions published 1968-2008) (3), the IUPAC (4), and the NIST (5).

1. CRC Handbook of Chemistry and Physics, 1st Ed., Editor David R. Lide, CRC Press, 1913, pg. 70. 2. Handbook of Chemistry, 6th Ed., Editor Norbert A. Lange, Handbook Publishers, 1946, pg. 58. 3. CRC Handbook of Chemistry and Physics, 89th Ed., Editor David R. Lide Jr., CRC Press, 2008. 4. IUPAC Periodic Table. 5. National Institute of Standards and Technology, Periodic Table.

Please click on the IUPAC and NIST links. The Wiki interactive periodic table is clearly incorrect. You will not see the Wiki interactive periodic table in chemistry textbooks.

There are many problems with the Wiki interactive periodic table:

The biggest error is La, [Xe]5d1 6s2 and Ac, [Rn]6d1 7s2 are placed in the f-block even though they have no outer electrons in the f-state. As you can see from the Wiki article content La and Ac are in the first position in the d-block (Group 3) with their d1 state as they have outer electrons in common with the d-block.

Insertion of the f-block (even if done correctly which the Wiki interactive periodic table does not) is not advised for multiple reasons:

Insertion of the f-block results in these 14 elements having no group numbers (in order to maintain the original group 1-18 designations). Or one has to renumber all the groups 1-32. Halogens would then be group 31. This will never be adopted as the group numbers help explain the element properties in that group. Group 31 for the halogens (F, Cl, etc.) gives no meaning. Or keep the original group 1-18 designations and assign some other group assignment to the f-block elements. In addition to being inconsistent with most of the periodic table this would add another difficulty. Elements within a group have similar properties or trends and adjacent groups different properties. Applying this to the newly labeled groups in the f-block is not appropriate/possible.

Did it not occur to you that the Wiki interactive periodic table is causing much confusion for chemistry students who see 14 elements with no group numbers, the elements La and Ac with their outer d1 state in the f-block, etc. There is very good reason why the f-block is not "just" inserted to make the periodic table look nice.

Please change the format of the Wiki interactive periodic table to look the same as International Union of Pure and Applied Chemistry, National Institute of Standards and Technology, etc. It is the same standard periodic table as commonly accepted and shown at the beginning of .

First of all, I did not single-handedly decide this, and I am not ignoring history.
The placement of lanthanum and actinium under yttrium may have been standard for many years, but this is also changing and IUPAC chooses not to recommend a specific form (their table places neither La nor Lu under Y). There are many good arguments on both sides. And yes, Sc-Y-Lu-Lr periodic table have appeared in textbooks: one example is Wulfsberg's Inorganic Chemistry. As can be seen from "The Flyleaf Periodic Table", this usage does not appear until after 1982, when Jensen's paper "The Positions of Lanthanum (Actinium) and Lutetium (Lawrencium) in the Periodic Table" first appeared. Thereafter textbooks are about evenly split between your proposed form (14CeTh) and the current form used at the top of the infobox (14LaAc), with a few attempting to stay neutral and use IUPAC's 15LaAc.
As Jensen says in his 2008 or 2009 paper (I think it's the former), the criteria for placing an element in the periodic table is to assign it to a block based on the orbitals its valence electrons are in, assigning it to a group based on the number of valence electrons it has available, verifying the validity of these assignments through checking trends across the block, group, and period in question, and finally verifying that the arrangement results in the elements appearing in order of increasing atomic number. For whether to place La or Lu below Y, we must go to the third criterion, as the first two don't provide a definitive answer. And indeed Jensen makes a strong case for Lu below Y in his 1982 paper, based on the properties of the elements in question and the trends that result from each choice.
Why is the anomalous electron configuration of La and Ac absolutely prohibitive when it comes to assigning them to the f-block? By that argument thorium is also a d-block element, given its electron configuration of [Rn]6d27s2! But nobody calls it that. Lawrencium has been experimentally measured to have an electron configuration of [Rn]6f147s27p1: but does anyone call it a p-block element? And if it can be considered an f-block element with an anomalous electron configuration, why can it not be considered a d-block element with an anomalous electron configuration? I think a better way of looking at the electron configuration of La and Ac is that, like Gd and Cm, they have anomalous electron configurations to get the stability of an empty (or in the latter case half-filled) f orbital, and are really f-block elements. Finally, in lutetium, the 4f electrons are not valence electrons: therefore it does not make sense to assign it to the f-block.
Group numbers have never been officially assigned to the f-block elements (some have tried), but is this not exactly the same situation as if they are detached from the main table? They still have no group numbers either way, and each column in the f-block still has only two elements at present. I agree with you that assigning group numbers to these columns is nonsensical due to the lack of any trends that should be present in a group, but surely inserting the f-block back into the main body doesn't change this situation.
While group 31 for the halogens gives no meaning, neither does the IUPAC-approved group 17. The halogens all have seven valence electrons and the group number that would be best for them is surely group 7 (VIIA, VIIB, VII – whichever style you prefer): this number is far more useful than 17, for example in the (8−n) rule.
The bottom line is that IUPAC allows both forms of the periodic table, either Sc/Y/La/Ac or Sc/Y/Lu/Lr. The long form periodic table is simply a differently laid-out version of the medium form periodic table that you will normally see, and is not as often seen merely because of the aspect ratio of paper fitting the medium form well and not the long form. This is not a constraint here, and prominent authorities such as Seaborg have preferred the long-form periodic table. Double sharp (talk) 12:29, 19 June 2014 (UTC)

IUPAC and NIST most definitely do place La and Ac under scandium and yttrium in group 3. The IUPAC table you reference clearly numbers elements 57-71 with La(57) under Y and again clearly numbers elements 89-103 with Ac(89) under La.

The vast majority of references, including IUPAC, NIST, and the Wiki page place La and Ac under scandium and yttrium in group 3. To state otherwise is simply not true.

The placement of lanthanum (and later on actinium) under scandium and yttrium in group 3 (IIIB) has been the standard for many years; for example, the first edition of the CRC Handbook of Chemistry and Physics published 1913, page 70 titled, “Periodic Arrangement of the Elements – Mendelejeffs (Revised to 1911)”, and the Handbook of Chemistry published 1946. This placement continues to be the standard; for example, the CRC Handbook of Chemistry and Physics, the IUPAC, and the NIST.

There is certainly room for discussion of alternative representations of the periodic table but to show the current Interactive Wiki Periodic Table and defend it as the commonly accepted form is without basis.

What is troubling is your defense of this non-standard format and then defending it on the basis that it is better than the standard format. In addition your justification comes across as informed but a good deal of it is obfuscation. Most unusual for a neutral wiki volunteer.

If IUAPC, NIST, etc., intended to place Lu and Lr in group 3 in the d-block they would have done so. The current incorrect Interactive Wiki Periodic Table places Lu and Lr in group 3 in the d-block.

You state IUPAC, NIST, etc., do not insert the f-block due to a lack of space on the printed page yet you give an online IUPAC reference. There is no restriction to IUPAC and NIST showing the inserted f-block online yet they do not (for the good reasons stated above; and it results in a gap between the group 3 elements (Sc, Y, La, Ac) and the group 4 elements. The preference, historically, has been to show gaps between blocks as a visual aid not within blocks).

This discussion is not a printed page format issue.

La, [Xe]5d1 6s2 and Ac, [Rn]6d1 7s2 are in the first position in the d-block (Group 3) because of their d1 electronic ground state and properties. The Wiki Interactive table does not show this.

Instead the Wiki Interactive periodic table shows La, [Xe]5d1 6s2 and Ac, [Rn]6d1 7s2 in an unnamed group in the f-block yet both elements have no outer electrons in the f-state (as clearly shown by their electron configurations).

Why is a wiki volunteer defending a non-standard periodic table with invalid statements?

Using your reasoning Cu, [Ar]3d10 4s1 and Zn, [Ar]3d10 4s2 would be moved to the s-block.

Lu, [Xe]4f14 5d1 6s2 and Lr, [Rn]5f14 7s2 7p1 are best left in the f-block because both elements have outer electrons in the f-state (as clearly shown by their electron configurations).

The Wiki Interactive Periodic Table format must be self-consistent with the format of other online periodic tables by established scientific bodies such as IUPAC and NIST. — Preceding unsigned comment added by (talk) 02:52, 20 June 2014 (UTC)

No, they don't. If they had wanted to unequivocally dictate that the composition of group 3 is Sc/Y/La/Ac, they would have done so by putting La and Ac in the main body, followed by a note leading to the lanthanides and actinides at the bottom of the periodic table. So group 3 would look like Sc/Y/La/Ac: followed by a space with boxes reading (58-71) and (90-103): and then group 4 (Ti/Zr/Hf/Rf). This is not what IUPAC does: they sidestep the issue. How do you know they didn't literally mean that all the lanthanides and actinides fitted under Sc and Y?
The online IUPAC reference is the one you yourself mentioned, and that is why I commented on it. The medium period layout probably stemmed from page limitations IIRC. While it is still commonly used even elsewhere (I would imagine because the Web gives you freedom to use any aspect ratio you'd like, and it's easier to use the traditional format), now that the restriction is not present, it is absolutely OK to use an equivalent form. In fact we don't always use the long form: we just use it here because the medium form won't fit the limited width as well. This isn't even something like using the Janet periodic table (putting He over Be) or some of those formats that put Be and Mg over Zn, etc. All the elements are in the same locations as the medium table implies they are. As for the La/Lu issue, different forms of the medium table imply differently on this issue.
No, La and Ac are not d-block elements, as I have said earlier: they are f-block elements with anomalous electronic configurations. Or do you think the electron configurations of almost all the f-block elements are anomalous, because most of them don't have the 5d1/6d1 electron that was filled in La and Ac? Even their properties indicate this: the trends you get when plotting Sc-Y-Lu resemble the d-block groups very closely, unlike the trends you get when plotting Sc-Y-La. See Jensen's 1982 article for some graphs. Putting La and Ac in the d-block means that in group 3 alone (and in none of the other d-block groups), there is no addition of the filled 4f14 subshell when going down from period 5 to period 6.
Please read carefully. I never said that thorium was a d-block element: I merely pointed out that by your argument it should be one because of its [Rn]6d27s2 electron configuration. Naturally I disagree with that, and hence I think that Cu and Zn should be handled the same way: they are d-block elements, although Cu has an anomalous [Ar]3d104s1 electron configuration.
Finally, if you're using the standard definition of what an outer electron is (I'm assuming a valence electron), the f electrons in Lu and Lr are not outer electrons as they don't participate in chemical bonding: the 5d1 and 6s2 electrons of Lu are lost to form the Lu3+ ion, with the 4f electrons firmly part of the core and not participating in chemical reactions (the 4f shell being well-localized near the atomic nucleus). Just like the next elements (Hf and Rf) the s and d electrons (p instead for Lr) are the valence electrons, and hence these elements are in the d-block. Double sharp (talk) 05:01, 21 June 2014 (UTC)
(P.S. I wouldn't oppose changing the long table to a medium table if there was a clear consensus to do so, but the issue has been raised several times and there never seemed to be one each time. What I personally cannot support is following Sc/Y/La/Ac when arguments based on the properties of the elements oppose this format and IUPAC and NIST do not use it. Sc/Y/*/** would be the best, remaining neutral, but that is tricky to do with the long table without grotesquely stretching the Sc and Y cells: hence for the long table Sc/Y/Lu/Lr is probably best.) Double sharp (talk) 05:09, 21 June 2014 (UTC)
re IP. An introduction. Here I'll write about the graphical presentation, which is secondary to the facts we actually want to show. A PT graph follows scientific statements. I have shaped many of the PT's here at enwiki, usually following an outcome of a discussion at WT:ELEMENTS. This is about the drawing of PTs; the actual facts the PT shows is beyond my area of knowledge (I can read & follow those PT content discussions, but not make new statements). I note that similar discussions exist for: which are the metalloids?, are group 12 elements a post-transisiton metals?, what to name those post-transition metals after all?, and —less hot— the placement of hydrogen (H). At this point, please note that all these are not internal wiki issues, but they reflect topics as they exist in the scientific world.
In most or all PTs at en:wikipedia, when we show a positioning it is that group 3 is Sc/Y/Lu/Lr. This is usually a 32-column PT. In 18-column PTs, we show group 3 and the asterisks being ambiguous (as in this PT).
Let me split the topic. IP conflates the PT graph with statements of element positioning. The group 3/f-block/La&Ac/Lu&Lr/ topic as scientific statements and facts is independent of and prior to any presentation form. The PT graphic should simply represent whatever the outcome is, maybe even showing an ambiguity in the theories. From this I note that IP says (my words): "the 18-column form is better because it shows the facts as they are correct". Whether these statements are correct and which statements to use in our PTs, I'll leave to others for now (Double sharp addresses this above). Such a scintific debate can very well be described in an article or article section, for example in group 3.
18-column variants. Contrary to what IP seems to think, there is no single 18-column PT standard with regard to this issue. We could also show an 18-column PT with Lu/Lr in group 3 explicitly; a statement IP opposes. So "the" 18-column format does not say anything about these placements.
Graphic clarity. For any graphic presentation, I require that it is unambiguous in what it conveys. (If we want to show the dual options for hydrogen, then we must find a way to show that scientific ambiguity graphically unambiguous!). We should not ever put graphic ambiguity on the readers screen. In this topic of the outplaced set of elements, it must be clear how to position that satellite elements back into the periodic table. This cut-and-paste exercise may not introduce any unclarities or questions, either when taking them out to below or putting them back in. I repeat: no graphic ambiguity.
The solution IP proposes make use of the graphic ambiguity of the 18-column PT: that 18-column variant graphically hides the group 3 discussion, it simply does not show any facts or discussion. But in a 32-column presentation we cannot hide it. Again, I refuse to use an 18-column PT because of this 'advantage'. It leaves the reader with questions.
18-column PTs questioned. Actually, our commonly used PT (such as the first one here) does have an ambiguity. The asterisks show the replacement positions of the two elements rows clearly (I hope). But when I cut-and-paste 15 elements in there (say the LN), I have no clue as to what happens with that group 3 column. Are those 15 elements squeezed into one cell (a sin in PT structuring, but graphically suggested)? Are Sc/Y glued to group 2 or to group 4? Are Sc and Y cells somehow stretched to span the whole area between group 2 and group 4? This is the graphical imperfection in the PT we use. (btw, all of this could be clarified by adding a gap column between groups 2–3 [16] or between groups 3–4. This requires a choice of group 3 completion as is our topic here).
The IUPAC PT that IP has linked to [17] is a graphically a rejectable form and a horror. Those vertical dashed lines making a vertical connection in group 3: what does that say? Are La and Ac really below there in group 3 (suggesting some extra periods)? Or if I copy-paste elements La and Ac into periods 6 and 7, what to do with the remaining 2×14 elements? Are these Desert Island elements? And still the gap question for periods 4 and 5 is not clarified. IUPAC should never have shown this graph to the world.
Some more bad graphics (what does the graph say about the group 3 area? How to cut&paste LN/AN?): [18], [19], [20] (ouch), [21], [22], [23],
Also, I find it a bit weird to use "historical" as an argument. The PT structure has always been adjusted in its 150+ years. Why use a form 100 years old when the LN/AN were not even recognised?
Conclusion. The topic IP raises should be split into 1. what facts to show (periodic table scientific), and 2. then follows: how to show that outcome unambiguously in any PT. I am amxious to learn what facts we should show. If someone can show it in a 32-column PT, we can graph that into an 18-column for sure. -DePiep (talk) 12:28, 22 June 2014 (UTC)
Yes indeed, the historical argument is quite weak: if we're going to use this argument, why not go back to the beginning of the story and use Mendeleev's original 8-column short-form periodic table? It's still very popular in the CIS even now. Double sharp (talk) 13:21, 22 June 2014 (UTC)
re IP: The Wiki Interactive Periodic Table format must be self-consistent with the format of other online periodic tables by established scientific bodies such as IUPAC and NIST
NIST? Never heard of, never met a link! That's the "National institute of Standards and Technology" then (which Nation??). But thanks. Now, for the moment, about their "standards". The NIST PT graph (nice!) still does not resolve the group 3 area: when I insert the LN/AN elements in there as they show, what or where or how are Sc/Y to go?
Your IUPAC PT, as I wrote above, has an illegible graph. I wrote: It is a graphically a rejectable form and a horror. Those vertical dashed lines making a vertical connection in group 3: what does that say? Are La and Ac really below there in group 3 (suggesting some extra periods)? Or if I copy-paste elements La and Ac into periods 6 and 7, what to do with the remaining 2×14 elements? Are these Desert Island elements? And still the gap question for periods 4 and 5 is not clarified. IUPAC should never have shown this graph to the world.
Please, please show me your 32-column PT. -DePiep (talk) 01:40, 24 June 2014 (UTC)
I think what (s)he wants is a 32-column table where La and Ac are in group 3, and the remaining 2×14 elements are spliced between La and Hf, like this one. (That old revision moreover gives the first 4 hypothetical period 8 elements, to show where they would fit. But it breaks all the blocks except the p-block.) Double sharp (talk) 15:14, 24 June 2014 (UTC)

Yes IUPAC side-steps the issue of the ‘best’ periodic table format/presentation for many good reasons. Some of which have been discussed above (f-block elements have no group numbers; “Elements within a group have similar properties or trends and adjacent groups different properties. Applying this to the newly labeled groups in the f-block is not appropriate/possible.”; visual gap within a block; etc.)

However the IUPAC has publications which make clear the group 3 elements are Sc, Y, La, Ac. For example the 2014 publication:

IUPAC-NIST Solubility Data Series. 100. Rare Earth Metal Fluorides in Water and Aqueous Systems. Part 1. Scandium Group (Sc, Y, La)

They do this because of over 100 years of placing La in group 3. See detailed comments and references above.

The group 3 d-block elements are: Sc, [Ar]3d1 4s2 Y, [Kr]4d1 5s2 La, [Xe]5d1 6s2 Ac, [Rn]6d1 7s2

The Wiki Interactive Periodic Table places La, [Xe]5d1 6s2 and Ac, [Rn]6d1 7s2 in the f-block. This creates many problems and is a step backwards.

If we start moving elements around because of ‘anomalous’ electronic configurations then there are many elements that need moving. One cannot selectively justify one argument for moving some elements and not apply the same to other elements.

If one applies your reasoning that Lu and Lr do not belong in the f-block because, “the 4f electrons firmly part of the core and not participating in chemical reactions”, then that means the entire 4f elements/row don’t belong in the f-block!

Lu, [Xe]4f14 5d1 6s2 and Lr, [Rn]5f14 7s2 7p1 are best left in the f-block because both elements have outer electrons in the f-state (as clearly shown by their electron configurations). This is commonly accepted practice, e.g.,

Keeping Lu, [Xe]4f14 5d1 6s2 and Lr, [Rn]5f14 7s2 7p1 in the f-block makes sense for several reasons. Even though the tightly held 4f electrons in the lanthanides do not participate in chemical reactions the 4f electrons do play a role in their properties. It is for this reason there is active research in lanthanide-doped semiconductors with small amounts of lanthanide ions and the important role of their 4f transitions. For example the publication titled, “Synthesis, Structure, and Molecular Orbital Studies of Yttrium, Erbium, and Lutetium Complexes Bearing Pyrazolato Ligands: Development of a New Class of Precursors for Doping Semiconductors”.

The Wiki Interactive Periodic Table incorrectly removes Lu, [Xe]4f14 5d1 6s2 from the f-block and incorrectly places La, [Xe]5d1 6s2 in the f-block, yet there is obviously no way the 4f electrons in La can play any role in any process because it has no 4f electrons!

For all the detailed defense of the unusual Wiki Interactive Periodic Table it is surprising that there is any confusion as to what standard format I am referring to. As already stated many times the format of the first two periodic tables listed at are fine to use for the Wiki Interactive Periodic Table, as are the IUPAC periodic table, the National Institute of Standards and Technology periodic table, or any of these:

Although I would recommend the Wiki Interactive Periodic Table uses the IUPAC format.

Please note I am not asking or suggesting that the discussion of these problems not be present in Wiki articles of which there are 100’s of Wiki pages on the periodic table and the individual elements.

However the current Wiki Interactive Periodic Table is definitely a misrepresentation of what is the commonly accepted format (see IUPAC, NIST,

The current Wiki Interactive Periodic Table incorrectly places La, [Xe]5d1 6s2 and Ac, [Rn]6d1 7s2 in the f-block and incorrectly places Lu, [Xe]4f14 5d1 6s2 and Lr, [Rn]5f14 7s2 7p1 in the d-block. The word “incorrectly” is used for the many reasons discussed here and above. — Preceding unsigned comment added by (talk) 23:26, 24 June 2014 (UTC)

No, it doesn't mean that the entire row doesn't belong in the f-block. To take the example of Yb (although it will really work for any lanthanide except La and Gd), [Xe]4f146s2, two 6s and one 4f electron are ionized to make the tripositive ytterbium cation with electron configuration [Xe]4f13. Clearly the 4f electron is active here. Indeed this holds for every lanthanide except La and Gd, which have anomalous electron configurations, as I have said many times. (Ce's 4f electron is ionized when it is oxidized to Ce4+.) And this says nothing about other elements: many also have anomalous electron configurations, like Cr, Cu, Pd, etc. Is it so hard to believe that La and Ac are also like this? And why do your arguments suggest that Lr's [Rn]5f147s27p1 electron configuration prohibits it from being a d-block element, but has absolutely no bearing on whether it is an f-block element?
You don't have to move any other elements. Cu is in group 11, as that is where it would be if it had the expected [Ar]3d94s2 electron configuration. Thus La is the first f-block element, as that is where it would be if it had the expected [Xe]4f16s1 electron configuration. Lu presents no argument with its [Xe]4f145d16s2: it has the right configuration to be under Y. After all Hf with [Xe]4f145d26s2 is under Zr.
I can handle a visual gap in the d-block, and you don't even need one in Sc/Y/La/Ac if the cells read Sc/Y/La*/Ac** or similar. And simply removing the f-block from the main table doesn't solve the problem of the f-block columns: they are still columns, and the outermost ones are still adjacent to groups 2, 3 or 4 (depending on format), because that is where the asterisks seem to be telling me to place them. Double sharp (talk) 02:44, 25 June 2014 (UTC)

On the basis that Lu 4f electrons do not participate in bonding you stated it as a reason not to include Lu in the f-block. The 4f electrons for all the Lanthanides do not participate in bonding, and we are in agreement this is not a reason to remove them from the f-block. This shows the importance of electron configurations and where elements are placed, and Lu [Xe]4f14 5d1 6s2 which is nearly always Lu3+ [Xe]4f14 has outer 4f electrons that can play a role as discussed above in the example of lanthanide-doped semiconductors.

That is why their publication is titled, “Synthesis, Structure, and Molecular Orbital Studies of Yttrium, Erbium, and Lutetium Complexes Bearing Pyrazolato Ligands: Development of a New Class of Precursors for Doping Semiconductors”.

It is not titled, “Synthesis, Structure, and Molecular Orbital Studies of Yttrium, Erbium, and Lanthanum Complexes Bearing Pyrazolato Ligands: Development of a New Class of Precursors for Doping Semiconductors”, for the obvious reason that La, [Xe]5d1 6s2 has no 4f electrons.

I am also in full agreement with your statement, “I can handle a visual gap in the d-block, and you don't even need one in Sc/Y/La/Ac if the cells read Sc/Y/La*/Ac** or similar.” This what the IUPAC, NIST and the above examples do. When will the Wiki Interactive Periodic Table show this format? — Preceding unsigned comment added by (talk) 19:32, 26 June 2014 (UTC)

As I have said many times above, no, they don't. They use Sc/Y/*/**. Double sharp (talk) 14:13, 1 July 2014 (UTC)
IUPAC doesn't have a position on the composition of group 3. A number of chemists in the 1920's and 30's assigned Lu rather than La to group 3 on the basis that the chemical properties of Y, and Sc to a lesser extent, were closer to Lu. That La and Ac are sometimes shown as group 3 members appears to have originated in the 1940s based on electronic configurations and the concept of the differentiating electron. As noted, arguments as to the composition of group 3 should turn upon more than the single concept of a differentiating electron. There remains a reasonable body of physics and chemistry-based evidence favouring the assignment of Lu and Lr to group 3. Eric Scerri has recently presented arguments [24], including those based on the construction of the 32-column form of the periodic table, supporting the assignment of Lu and Lr to group 3. IUPAC have since asked him to form a working group with a view to making this change official. See also Jensen's 2009 commentary on this question, here. Sandbh (talk) 11:36, 25 June 2014 (UTC)

IUPAC has for many years not wanted to force this issue because there is no one correct periodic table format when it comes to the f-block. But what is clear is the preferred representation as shown by: the first two periodic tables listed at the IUPAC periodic table the National Institute of Standards and Technology periodic table

And 2014 publications such as “IUPAC-NIST Solubility Data Series. 100. Rare Earth Metal Fluorides in Water and Aqueous Systems. Part 1. Scandium Group (Sc, Y, La)” are unambiguous.

I agree with you that the 18-column form is prevalent. I don't like the fact that the lanthanides and actinides are relegated to the status of footnotes, nor do I like the fact that the IUPAC table shows 15 lanthanides, rather than 14, due to indecisiveness as to the composition of group 3. Since the 18 column-form is prevalent it's reasonable to show this as the Wikipedia periodic table. Given the shortcomings of this form I think having the 32-column form in element infoboxes is a reasonable way of accommodating (a) prevalence and (b) showing what's really going on. Sandbh (talk) 00:11, 29 June 2014 (UTC)

“That La and Ac are sometimes shown as group 3 members appears to have originated in the 1940s based on electronic configurations and the concept of the differentiating electron.” Sorry but this 100% incorrect.

Lanthanum was placed under scandium and yttrium in group 3 over 100 years ago. See the first edition of the CRC Handbook of Chemistry and Physics published 1913, page 70 titled, “Periodic Arrangement of the Elements – Mendelejeffs (Revised to 1911)”.

Lanthanum was placed under scandium and yttrium in group 3 in the major chemistry reference books and still is. Examples are the Handbook of Chemistry published 1946 and decades of the CRC Handbook of Chemistry and Physics.

I should've been clearer. IMO, since about the 1940s, authors who show La in group 3 have done so explicitly on the basis of the electron configuration argument; or tacitly on the basis of how other authors have depicted their PTs. In both cases, strong physical and chemical arguments for placing Lu in group 3 have been discounted or overlooked. Sandbh (talk) 00:11, 29 June 2014 (UTC)

The Scerri link refers to Jensen’s early paper and Jensen’s paper is selective in omitting the reasons why La and Ac were and are placed in group 3.

He discusses the relevance of electron configurations well enough, I think. And he gives the physical and chemical arguments for his case. Sandbh (talk) 00:11, 29 June 2014 (UTC)

You are restating what I wrote, he did provide the physical and chemical arguments for his case. He did not discuss the physical and chemical arguments for why La and Ac were and are placed in group 3 and the implications of moving La and Ac to the f-block (which are discussed above).

One has to look at the pros, cons, and implications of placing elements in the periodic table or changing their positions.

In addition the f-block, as discussed in above previous posts, are not groups like the other periodic table groups and this is a reason not to insert them or one ends up with unnumbered/unnamed/non-groups being presented as groups. Hence the IUPAC presentation which they are unlikely to change.

See here, for an alternative view, including that of Eric Scerri. Sandbh (talk) 00:11, 29 June 2014 (UTC)

However whatever changes are proposed the Wiki Interactive Periodic Table should be reflecting what is the preferred periodic table presentation as shown by: the first two periodic tables listed at the IUPAC periodic table the National Institute of Standards and Technology periodic table etc. (see links in previous post).

(As an aside where was Jensen’s emotional commentary published? Jensen has formatted it to look like a journal publication but I could not find it.) — Preceding unsigned comment added by (talk) 20:27, 26 June 2014 (UTC)

I understand it was published in a condensed form in the Journal of Chemical Education. I further understand that his commentary may appear to be somewhat emotional as he perceived that he had been subjected to an "ad hominen" attack, without warning. PS: I collapsed your earlier links as they display poorly on my ipad. Sandbh (talk) 00:11, 29 June 2014 (UTC)

Most unusual to show a paper in journal format, and have it referenced by others as a publication, when it is not a journal publication.

Here is the condensed form Sandbh refers to. Double sharp (talk) 15:14, 8 July 2014 (UTC)

After 5 yrs unnoticed[edit]

... and people possibly being misdirected, removed "Nor-" from Template:Orgchemsuffixes, because it does not mean "no residue". See Nor-. Le Prof Leprof 7272 (talk) 05:05, 21 June 2014 (UTC)

You keep me puzzled on why someone should wait ten years before using knowledge. [25]. -DePiep (talk) 12:53, 22 June 2014 (UTC)

Calling all cars[edit]

Still need Ochemists, biochemists, etc. with natural products expertise to tune into the Natural products article. Things are beginning to move again, and are more peaceful, but secondary source-wielding experts still desperately needed. (Where "god" stands for "grumpy old doc".) Le Prof Leprof 7272 (talk) 05:12, 21 June 2014 (UTC)

Discussion on providing detailed synthetic schemes in articles at the Medicine project page[edit]

I've started a discussion over on the Medicine Project page about the inclusion of detailed synthetic routes in articles. I apologize for not posting here earlier and now realize that this page was probably the most appropriate forum for the discussion. Please accept my belated effort to correct this mistake.

As you will see there, I am concerned about the recent proliferation of very detailed synthetic schemes for in many pharmaceutical drug articles. Although a PhD synthetic/medicinal chemist myself, I am concerned that these very detailed routes are 1) incomprehensible, and 2) of little interest to the vast majority of our readers. As a third point, the synthetic routes being added seem in many cases to be arbitrarily chosen from among the dozens of different routes available in the literature, and thus lack notability.

It is not my intent here to trivialize the importance of chemistry or the value of synthetic expertise, as synthetic chemistry is in fact my own vocation. Please take a look and offer your comments. I suspect there will be some disagreement/opposition, but if you have any ideas on how to address the concerns I have raised it would be very much appreciated. I'm not looking to drive an agenda here, just to figure out a mutually acceptable way to address what I see as an issue of keeping the level of the science appropriate to our audience. Formerly 98 (talk) 13:18, 22 June 2014 (UTC)

Rose oxide - isomers[edit]

The article on rose oxide states "The compound has a cis- and a trans-isomer, each with a (+)- and (−)-stereoisomer". But I see a molecule with two carbon atoms that would each independently act as a centre of chirality, and a double-bond which cannot be involved in cis-trans isomerism.

The article also contains this diagram Rose oxide isomers which appears to me to show something that I would not call cis/trans isomerism.

Which is confused, me or the article? Maproom (talk) 10:28, 26 June 2014 (UTC)

The cis/trans isomerism is limited to double bonds, in this case it relates to the positioning of the groups relative to the plane of the cycle. Plasmic Physics (talk) 11:30, 26 June 2014 (UTC)
I assume you mean "... is not limited ...".  Ok, it makes sense now, thanks. Maproom (talk) 12:01, 26 June 2014 (UTC)
Darn, for some reason I keep making a habit out of missing out a "not". Yes, that is what I meant to say. Plasmic Physics (talk) 08:01, 28 June 2014 (UTC)

Monoatomic Elements[edit]

Back in 2009, Archive 13 or 14, there was discussion on what to do with the topic of "monoatomic gold". Since about that time, I have researched in depth the topic of monoatomic elements, particularly relating to Au and the the PGE's. I found that once one sifts through all the new age chatter about "ormus" (basically magnesium hydroxide) and discredits the promotional hype of "white powder gold" product vendors, that there are scintillas of truth regarding these substances. Whether or not they are monoatomic is questionable, but they certainly appear to be allotropic forms of the elements involved. (Yes, I am aware that these metals do not have allotropes.) To further substantiate the few seemingly valid claims, I was fortunate to meet and discuss the subject with the PhD chemist who did most of the chemical extraction and purification of these substances. Enlightening to say the least. I am posting this to see if there is any interest in resurrecting this topic after five years. Your thoughts? JohnsonRick (talk) 23:48, 27 June 2014 (UTC)JohnsonRick

If you have reliable sources then there is basically no need to ask. I struggle to see the validity of calling nano-scale assemblies of elements "allotropes" of the elements concerned. The structural "chemistry" at those scales doesn't seem comparable with what happens at the bulk scale. Sandbh (talk) 04:59, 28 June 2014 (UTC)
Having good sources is half the requirement, it is also helpful if you are moderately fluent in the chemistry of metals. Atoms of elements are usually mentioned in the articles on those elements. A good start would be to leave a note at Talk:Gold. --Smokefoot (talk) 14:19, 28 June 2014 (UTC)

Infobox hydrogen at TFD again[edit]

{{Infobox hydrogen}} is up for deletion again. Please discuss at Wikipedia:Templates for discussion/Log/2014 June 28#Template:Infobox hydrogen. --Redrose64 (talk) 23:09, 28 June 2014 (UTC)

List of 2,4-D manufacturers[edit]

Are lists like the one mentioned above of any use or significance? --Yikrazuul (talk) 09:08, 29 June 2014 (UTC)

No. Only thing I can brainstorm would be if some special notability of their doing so (together forming a coalition or trade-group, or being together involved in some major legal or other newsworthy situation, etc.). Even then, seems likely to be unworthy of a stand-alone list article. Unless there's something notable about this group as a whole or the members of it doing the identified activity, I think at best it's just a business directory; see also Wikipedia:STANDALONE. Given the chemical involved (which might be controversial in various ways), we need to be especially careful not to make any negative connotations or implications by placing such a prominent identifier on the listed companies. DMacks (talk) 04:12, 1 July 2014 (UTC)
I have AfD'd the article. As I state there, the opening statement could be used in the article about the compound, the list is not necessary. I find this article/principle also US-centered, this is not a 'List of 2,4-D manufacturers', this is a 'List of 2,4-D manufacturers in the US'. --Dirk Beetstra T C 10:22, 1 July 2014 (UTC)

Isomer names[edit]

The article Citral clearly states that citral is either or both two different substances, geranial and neral, which are cis-trans isomers. Yet in its infobox, the article gives a single IUPAC name, CAS number, PubChem number, ChemSpider number etc. for "citral". I had assumed that these names and numbers were meant to be identifiers. Was this naive of me? or is the infobox misleading? Maproom (talk) 12:42, 29 June 2014 (UTC)

Citral is a mixture, so unless the isomers rapidly interconvert at standard conditions, is does not even warrant a Chembox. A table with a few simple properties at common compositions, and content describing how the properties vary with composition, should suffice. That being said, mixtures can also have identifiers, to an extent. The rule of thumb is, if you are in doubt over whether an E/Z mixture is separable, it usually is. Plasmic Physics (talk) 21:44, 29 June 2014 (UTC)

Both the mixture and pure isomers appear to have separate identifiers, that along with the common names would imply relative stability. Given time and effort the chembox could be expanded to include all the variables. However, I should point out that chembox code isn't really designed for this, I did it once for periodic acid and that involved using some of the parameters in ways they weren't intended to be.

E/Z-citral E-citral Z-citral
Cas 5392-40-5 141-27-5 106-26-3
Chemspider 9372550 553578 558878
Pubchem 8843 638011 643779

On a side note, it appears that the name 'geranial' has something to do with with the Geraniums. Likewise Neral appears to be derived from Neroli. Project Osprey (talk) 23:00, 29 June 2014 (UTC)

Geraniol has also been called “lemonol” and “rhodinol” (rose). Its structural isomers include linalool (lignum-aloes), citronellal or rhodinal, eucalyptol, lavandulol, and menthone (mint).—Odysseus1479 01:03, 30 June 2014 (UTC)

The chembox should here just be having the data for the mixture, and in the text it should link to the E and the Z compounds' articles. This chembox on Citral may become a bit minimalistic. Don't think too binary about it. --Dirk Beetstra T C 03:53, 30 June 2014 (UTC)

Some other articles dealing with pairs of enantiomers are carvone and malic acid: each has a single chembox, giving a single IUPAC name. Would such articles be better with two chemboxes, one for each substance? (I don't think infoboxes are restricted to one per article: Klein graphs has two infoboxes, one for each graph.) Is there a reliable free online source where I can look up official names for organic chemicals? Maproom (talk) 10:25, 30 June 2014 (UTC)
No, an article can only have one Chembox, that much is stated explicitly somewhere. And again no, there is no reliable source for official names. Plasmic Physics (talk) 10:52, 30 June 2014 (UTC)
Agree with Beetstra: One doesnt need to get too litigious about chemboxes and isomers. Lots of compounds are available as mixtures and readers want some data on that mixture. We serve readers, period. We adapt to the chemistry, chemistry does not adapt to Wikipedia. It takes expertise to interpret data, but that is always the case. --Smokefoot (talk) 12:32, 1 July 2014 (UTC)


FYI, significant number of mislinks heading to wrong article. Discussion needed on what to do with redirect. In ictu oculi (talk) 10:49, 30 June 2014 (UTC)

AfC Submission - Anion Exchange Resin[edit]

Got a chem-related submission at Draft:Anion Exchange Resin. Looks good at first glance to me, but I'm curious about the overlap with ion-exchange resin (if any). Is anion-exchange resin particularly notable enough to have its own article, or should it possibly be merged with ion-exchange resin? Looks like a lot of overlap coverage between the two pages, and unfortunately chemistry wasn't my forte in high school. Thanks, ~SuperHamster Talk Contribs 23:28, 30 June 2014 (UTC)

An anion exchange resin is a type of ion exchange resin. Cation exchange resins also exist, as explained in the ion exchange resin article. In my view the draft anion exchange resin article should be rejected, as its material is already covered, better, in the ion exchange resin article. Maproom (talk) 05:59, 1 July 2014 (UTC)
I also note that the list of "common anions" in Draft:Anion Exchange Resin, as well as having numerous errors, starts with hydride ions. You won't get hydride ions in an ion exchange resin - they react vigorously with water. Maproom (talk) 13:27, 1 July 2014 (UTC)

Noyori asymmetric hydrogenation[edit]

Can some people have a look at Talk:Noyori asymmetric hydrogenation?. Thanks! V8rik (talk) 21:32, 7 July 2014 (UTC)

Probably should start by defining the term "Noyori asymmetric hydrogenation" because it is difficult to discuss mechanisms without knowing the process being analyzed. Not trying to be snarky here, but Noyori and co invented a lot of catalysts that hydrogenate ketones. --Smokefoot (talk) 02:36, 8 July 2014 (UTC)

Support for Chemical table files[edit]

As of now, images of structural formulas have to be created using third party software and converting the output to SVG or PNG. With MolHandler we aim for a solution capable accepting and rendering chemical markup files and providing a web-interface for easily creating, modifying and re-mixing formula files. This does not only make re-using existing structures easier and simplifies creation of structures, moreover it allows Wikis to adopt a unified style for rendering these structures, makes structures searchable (sub-structure search) allows pulling, pushing and verifying data from big databases like ChemSpider and PubChem. In the future we plan to enable support for spectra and more sophisticated file formats to have at least some minimum support forchemistry-related Wiki-works.

I am currently looking for features you would find helpful as well as your opinion of what is needed to deploy MolHandler to Wikipedia and therefore created a test wiki at which you can create user accounts (and do everything you ever wanted to do). A non-exhaustive list of features is available for raking by drag&drop. Or just write here what you at least want, what you would like to see soon and what is less important to you.

If you want to upload MOL or RXN files instead of SVGs and PNGs in future, go to, test and say, "YES to MolHandler"!

-- Rillke (talk) 13:00, 8 July 2014 (UTC)

  • This sounds promising. To report issues at bugzilla is too much trouble. Can we have a talk page on the mol Wiki to discuss the experiences? Graeme Bartlett (talk) 23:12, 8 July 2014 (UTC)
    • Of course. Thanks for your error report. Also note that I may delete stuff from MolWiki and migrate it to Bugzilla or Phabricator to be able to keep track of everything (Mailinglist threads and RfCs on other Wikis are running as well, in case you are wondering why). -- Rillke (talk) 11:14, 9 July 2014 (UTC)

Wikipedia talk:Articles for creation/Asymmetric Keck Allylation[edit]

Dear chemists: This old AfC submission will soon be deleted as a stale draft. Is this a notable chemistry topic? The text seems polished in a way that makes me wonder if some of it has been taken from a book or journal article. —Anne Delong (talk) 20:41, 8 July 2014 (UTC)

  • Organostannane addition possibly deals with the same reaction V8rik (talk) 21:59, 8 July 2014 (UTC)
  • Reasons given for rejection dubious. No wonder we rarely get to see new chemistry content. V8rik (talk) 22:04, 8 July 2014 (UTC)
  • Allylation is only a redirect to a small entry in Allyl, where a single asymmetric methodology is mentioned (but not Keck's). I could easily see having a real Asymmetric allylation article (there are multiple variants) and/or Keck allylation (it seems to be a standard Name reaction). I'm not sure the intersection of those two is sufficiently notable for a stand-alone article and this AfC does seem to need a lot of work to focus on its topic, but it surely seems like a viable starting point even if it eventually would get merged or distributed somewhere else. I agree with V8rik's thoughts about the rejection itself and a possible effect of it. DMacks (talk) 22:28, 8 July 2014 (UTC)
I agree with V8rik that the reasons for rejection of this draft are dubious. It would be a shame for this article to be deleted, so I have moved it to asymmetric Keck allylation. As DMacks notes, it may be better as a part of broader topic such as allylation. Please feel free to rework, merge, etc. the content as you see fit. But for now, at least it is saved from deletion. -- Ed (Edgar181) 22:36, 8 July 2014 (UTC)

  • To find other articles about chemistry that are sitting in Articles for Creation, try typing the word chemistry into this search box:

Those with a grey box at the top have never been submitted; those with a yellow box are currently waiting review; those with a pink box have been declined. Those with a darker pink bar across the middle of the box are abandoned and facing deletion, but this deletion is delayed for six months if even one edit is made. Please don't edit ones that you think should be deleted, but if you see an abandoned one that looks viable, feel free to fix it up. —Anne Delong (talk) 04:11, 9 July 2014 (UTC)

Anne has done a terrific job bringing these new articles to our attention and asking for comments, which many of us have made. Looking through the 150 more recent "articles for creation," almost all are requests for biographies. The following is a list of chemical topics, several of which have already gotten comments thanks to Anne's efforts.

--Smokefoot (talk) 11:44, 9 July 2014 (UTC)

  • Thanks, Smokefoot, for doing the sifting. I notice that this one has had its AfC template removed, and is just sitting there going nowhere, so maybe someone would like to take a look at it. —Anne Delong (talk) 12:48, 9 July 2014 (UTC)
Looks like The aza-Cope rearrangements is a live page created by the same editor just after he stopped doing extensive work on Wikipedia talk:Articles for creation/aza-Cope rearrangement ("this one"), so the draft can probably be deleted. As with many presumable student works, this looks like it needs a bunch of work to be something more usable by non-experts, and general MOS. DMacks (talk) 14:19, 9 July 2014 (UTC)
I moved The aza-Cope rearrangements to the title aza-Cope rearrangement, merged the editing history from the AFC, and redirected the AFC to the article. -- Ed (Edgar181) 17:51, 9 July 2014 (UTC)
  • Hi Anne, thanks for the effort and thanks for mobilizing the chemistry community V8rik (talk) 16:54, 9 July 2014 (UTC)
I moved Phenacene and Azaspiracid to mainspace and did a bit of cleanup on each. -- Ed (Edgar181) 17:51, 9 July 2014 (UTC)
Hey, this is great! Watch for a similar thread in the future about the ones in the new "Draft" namespace. —Anne Delong (talk) 01:03, 10 July 2014 (UTC)

Editor conflict at Steroid[edit]

@User:Boghog, please state your argument here, that the steroids article should be moved away from IUPAC and NLM Mesh inclusion of secosteroids, to a different definition. Note to readers, this is raised here because Bohog has strongly edited current text at the foundational Secosteroid stub, essentially reverting my earlier work, and in so doing changed the direction of the Secosteroid and ultimately the Steroid article — this despite (from Talk at Steroid) knowing he did not have consensus. The Steroid article cannot both proceed with, and without the seco-, nor-, and homosteroid classes included, and the opening lede secosteroid definition at Secosteroid is the first step in redefining the content of the Steroid article. Hence, the lede definition question is a central to the direction of the Steroid article. It also has implications for nor- and homosteroids, and aza-/oxa and other categories included in IUPAC, Dictionary of Chemistry, Nat Prod Reports, and other classic sources not sympathetic with the "secosteroids not steroids" initiative. The underlying issue appears -- based on Talk at steroid -- to be that Boghog only wants only tetracyclic structures included in the Steroid article.

Boghog, discussion to you. And I ask you again, belay your impatience to change the Secosteroid and Steroid articles immediately (because you are angry with me over the nat products article, or whatever). Please do not revert and disrupt the Secosteroids and Steroids articles as they are (regarding Secosteroid inclusion), until we can reach consensus, including hearing voices from this and other projects. (I have posted a brief notice at Pharmacology; feel free to post the question in other venues as well.) Le Prof Leprof 7272 (talk) 23:23, 15 July 2014 (UTC)

Do I now see it correctly, Leprof 7272, that you are busy changing the articles over (without prior discussion), and that Boghog has reverted that because they disagree with that? --Dirk Beetstra T C 03:32, 16 July 2014 (UTC)
Dirk, in separate, full answer to your question, the backstory is as follows. When I edited the Secosteroid article lede back in early May—an article which had see no attention from anyone in many, many months—I did so because the lede did not reflect the definitions appearing in the IUPAC, IUBMB, NLM, and more specific journal (Nat Prod Reports, J Nat Prod, Steroids) categories and coverages. These coverages speak of the subcategories of steroids (seco, nor, homo, hetero) as just that, subcategories of steroids, and not as compounds similar to them. I therefore made the change in May. There was really no one there to discuss this with, but, if you look at Steroid Talk, [26], you will see that every significant change I made there was accompanied by a Talk discussion section, asking input at times, or at least explaining the course of the editing. Note, I was brought to the Secosteroid article after beginning to add seco-, homo-, and nor- material to the Steroids site, and realizing there was a disparity in definitions between the two sites (see this material, [27]).
The edit to return the definition to "similar to" was then made mid July by Boghog, immediately following a discussion in Talk at Steroid. It seems clear from that discussion and his subsequent change of the Secosteroid language to "is similar", that the eventual aim is to move Steroid from covering all these subcategories, to just covering the largest tetracyclic 6-6-6-5 tetracyclic structural class. As I argue at Secosteroid talk, this defied all of the solidly sourced, broadly accepted categorizations and source coverages indicated above. If you want something on azasteroids, you go to steroid journals. If you want to name a secosteroid, it is in the IUPAC/IUBMB nomenclature article for steroids. If you are curious about a particular nor- or homo- or seco- steroid, you can find it in the venerable 2 vol Dictionary of Steroids. That some online medical dictionaries use language indicating "derived from" is immaterial because subcategories of steroids routinely derive from other subcategories. That other online medical sources use "is similar" language is worth mentioning, but should not trump IUPAC, IUBMB, and standard usage where seco-steroids are a subcategory in the whole of the steroid category (alongside homo-, nor-, hetero-, etc.). That says otherwise does not sway me, nor does attempting to interpret the NLM definition for steroids to exclude the secosteroids persuade, when the NLM Mesh overtly lists secosteroids as a subcategory of steroids. As I state at Secosteroid Talk, the desire for pedagogic simplicity and a few stray web dictionary definitions cannot trump the preponderance of usage in the major secondary sources and society and nomenclature tomes.
This is an important guiding question, hence the revert (something I have only done a handful of times here), and hence the request for broad participation. The issue is which understanding will guide the development of the Steroid article (which currently parallels the definition in place, [28], prior to Boghog's edit of this week). Le Prof Leprof 7272 (talk) 06:52, 16 July 2014 (UTC)
The proper place is to discuss this in on the secosteroid talk page, not here. In answer to Dirk's question, an older version of the article stated "a secosteroid is a molecule similar to a steroid but with a 'broken' ring". Leprof changed that to a secosteroid is a subclass of steroids. I subsequently restored the introductory sentence and added "Secosteroids are variously defined as a subclass of steroids or derived from steroids" with reliable sources to back both definitions. Then Leprof reverted my changes. There is a related discussion here. Boghog (talk) 03:56, 16 July 2014 (UTC)
Boghog has requested that the discussion take place here: [29], and I do not disagree. Le Prof Leprof 7272 (talk) 06:52, 16 July 2014 (UTC)
  • If the discussion started on that page then it should continue on that page. Otherwise it becomes fragmented and the eventual conclusion may get lost in the archives of this page... and if that happens we may end up having the same discussion some years later, when someone finds a half finished conversation on the article talk page and tried to finish it. Such things have happened before. Project Osprey (talk) 08:24, 16 July 2014 (UTC)

Borderline hydrides[edit]

Does anyone else see the issues with this article? It looks like a poorly written essay, with a confused subject. It looks like a random assembly of hydride statements, which after reading, I still don't know what defines a borderline hydride. The alternative definition covers something entirely different, which seems to be only semantically related. Is this article fixable, or should we look at scrapping it? Plasmic Physics (talk) 01:02, 28 July 2014 (UTC)

The term "borderline hydrides" appears in a handful of books - but mostly as descriptive English, rather than as a defined term. I can find almost no mention of it in journals, so it sounds like OR to me. That said, I like the idea of using dissociative chemisorption as a means of identifying covalent hydrides. We’ve had a lot of difficulty defining the bonding in transition metal hydrides, but presumably any that can form purely by exposure to hydrogen (under normal conditions) must be largely covalent? Project Osprey (talk) 08:53, 28 July 2014 (UTC)
It is not correct that hydrides formed by simple exposure to hydrogen must be covalent, that forms interstitial hydrides, if anything. How did you get that from the article in any case? Plasmic Physics (talk) 11:44, 28 July 2014 (UTC)
Shriver and Atkins, a popular inorganic text in the US and UK, uses the term "intermediate hydride" to describe the derivatives of zinc and copper. Greenwood and Earnshaw, which is more scholarly (more detailed, less of a textbook) classify hydrides as "customary to group the binary hydrides ... ionic, metallic, covalent, polymeric, and “intermediate” or “borderline"" but in the next sentence say that this classification "is unsatisfactory because the nature of the bonding is but poorly understood in many cases ... classification obscures the important point that there is an almost continuous gradation in properties - and bond types.." One recommendation might be to convert the article into a sort of disambigution page directing readers to copper hydride and zinc hydride.--Smokefoot (talk) 13:07, 28 July 2014 (UTC)