Wikipedia talk:WikiProject Chemistry

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WikiProject Chemistry (Rated Project-class)
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Should we write a ChemEd paper about running class projects?[edit]

It seems to me that we’re seeing more and more class projects aimed at this WikiProject but that the standard of work remains poor. A lot of time is being wasted trying to track down staff and students, not to mention trying to decide what to do with their gifts to us. The Journal of Chemical Education (amongst others) already has several papers about getting classes to edit chemistry pages on Wikipedia. Having read a few of them I can’t say I’m terribly impressed:

  • Moy, Cheryl L.; Locke, Jonas R.; Coppola, Brian P.; McNeil, Anne J. (2010). "Improving Science Education and Understanding through Editing Wikipedia". Journal of Chemical Education. 87 (11): 1159–1162. ISSN 0021-9584. doi:10.1021/ed100367v. 
  • Martineau, Eric; Boisvert, Louise (2011). "Using Wikipedia To Develop Students’ Critical Analysis Skills in the Undergraduate Chemistry Curriculum". Journal of Chemical Education. 88 (6): 769–771. ISSN 0021-9584. doi:10.1021/ed100017k. 
  • Walker, Martin A.; Li, Ye (2016). "Improving Information Literacy Skills through Learning To Use and Edit Wikipedia: A Chemistry Perspective". Journal of Chemical Education. 93 (3): 509–515. ISSN 0021-9584. doi:10.1021/acs.jchemed.5b00525. 

The focus of these guides is very much on the student experience and the opinion seems to be that so long as content is added with sufficient references then Wikipedia’s needs are met. The way things are described in the articles gives me the impression that the authors weren’t experienced editors at the time of writing.

McNeil et al do propose that articles be written in a sandbox and be checked by the course supervisor before being transferred to mainspace but mention this project only in passing. Martineau et al cite and adopt the same approach but fail to mention community interaction at all. Walker and Less is perhaps the best of the above papers but only because it talks in very general terms. What I’m wondering is should we write a ChemEd paper about running class projects? We could include fairly detailed advice how to set things up and what to write (and what not to!) and how to engage with the community so that the students’ hard work is actually worthwhile. --Project Osprey (talk) 13:11, 24 March 2017 (UTC)

There is already some general writeups around. We probably need some more on how to choose topics in chemistry. The environment course classes seems to have trouble selecting suitable topics in particular. Perhaps we can have a prepared list of suitable requested topics. Or we could have proposed topics run past the project here first. Other wise we end up with essays or academic papers insted of encyclopedia entries. Other issues relate to WP:MEDRS, and NPOV (often because so few sources are used) and excessively technical writing. Other more general problems are already covered, eg copyright infringement, edit warring, verifyability. Some instructors actually end up with good results in other areas. I will ahve a look for the course advice. Graeme Bartlett (talk) 01:52, 25 March 2017 (UTC)
The problem is the focus on creating new articles when it should be clear most have have already been created, I would personally advise class projects to focus on fact-checking and content correction. This would be a better skills training for students than blindly copying other encyclopedia's V8rik (talk) 11:15, 25 March 2017 (UTC)
To my mind most of the problems we have stem from 3 issues:
  1. Lack of communication: everyone knows that Wikipedia is community run but that somehow never translates to people trying to find the chemistry editing community. The lack of course-pages, preventing us from contacting these groups directly is related.
  2. Wrong content: we want general information of a broad topic but we always seem to get detailed information on a narrow topic.
  3. Conflicting desires: The students want to make a large body of work, that's clearly their own, and then add it in one massive edit. We don't work like that. This is probably the hardest point to fix, although sandboxes and use of articles for creation may help.
The existing literature doesn't address any of this. V8rik makes a valid point; the cleanup listing for WikiProject Chemistry ( provides a complete list of things that need checking, although I would strongly advise that we steer students away from contentious articles (e.g. PCB's). For my part I do think that new pages can still be created, particularly distinct small molecules ( here's a old list but if you turn the average bottle of shampoo around you'll find something that we don't list). What we would need to do would do is include explicit instructions on what to include and what not to. --Project Osprey (talk) 12:28, 25 March 2017 (UTC)


Wikipedia talk:WikiProject Medicine#Wikitext syntax change for chemicals--Ozzie10aaaa (talk) 01:20, 6 April 2017 (UTC)

Upcoming "420 collaboration"[edit]

Cannabis leaf 2.svg

You are invited to participate in the upcoming

"420 collaboration",

which is being held from Saturday, April 15 to Sunday, April 30, and especially on April 20, 2017!

The purpose of the collaboration, which is being organized by WikiProject Cannabis, is to create and improve cannabis-related content at Wikipedia and other Wikimedia projects in a variety of fields, including: culture, health, hemp, history, medicine, politics, and religion.

For more information about this campaign, and to learn how you can help improve Wikipedia, please visit the "420 collaboration" page.

---Another Believer (Talk) 17:26, 10 April 2017 (UTC)

Unclear article-names[edit]

The following two articles have names that are unclear about what their specific content is:

As they stand, the "aza" article is for when the nitrogen is anywhere (internal or terminal position of diene, or dienophile) and the "imine" article is specifically for when the nitrogen is the dienophile. But both are imine functional groups. The refs for the "imine" article only seem to use that term as part of phrases like "imine dienophile". Ahe only examples actually discussed at the "aza" article (after a generic scheme of the three possibilities) are ones with imine as the dienophile and that do not even procede by a classic Diels–Alder mechanism. So there is substantial overlap or unclear content scope, and one is missing content if one is to be a top-level with subarticles on specific variants. Apparently there is a lot to say about the imine-as-dienophile subtopic, so maybe the article on that topic should be given a more specific name? I'm open to suggestions for this or other solutions. DMacks (talk) 16:24, 16 April 2017 (UTC)

Here's a report from CAS. A lot of reviews mention aza-Diels-Alder (at least when the search term = Aza-Diels-Alder, zero hits for "Aza-Diels–Alder") and these two appear relevant, one new in a questionable venue, one old in a good journal. I looked at Boger's review hoping that he pointed to a super-classic example, but did not find one.
  • "Stereoselective Aza-Diels-Alder reactions" Rowland, Gerald B.; Rowland, Emily B.; Zhang, Qiang; Antilla, Jon C. Current Organic Chemistry (2006), volume 10, 981-1005.doi=10.2174/138527206777435463.
  • "Diels-Alder reactions of azadienes" Boger, Dale L. Tetrahedron (1983), volume 39, 2869-939. doi = 10.1016/S0040-4020(01)92154-4.

If I owned Wikipedia, the two articles would be merged and readers would be told of the diverse types of aza-DA including aza on the ene or the diene. --Smokefoot (talk) 18:31, 16 April 2017 (UTC)

Copyright issue with an image, can someone please quickly check two literature references?[edit]

I have Wikipedia:Media copyright questions#File:C3cs35486e-f1.gif posted at the media copyright questions page about the image File:C3cs35486e-f1.gif which is included on the artificial enzyme page. It was uploaded as "own work" by Wiki nju001 in 2015. The information in the image is seen in this supplementary data file from doi:10.1039/C3CS35486E, and the image has been reproduced with permission from the RSC in a book attributing the source as doi:10.1039/C5QI00240K. This second paper in Inorg. Chem. Front. was made available online four days before the upload. The uploader has not edited since that day. Would someone please establish if either of these papers actually includes the image? The image is hosted at commons but may have been uploaded to en-WP first. Either way, it seems to me that the image is a copyvio and, if not, the attribution in the article is inadequate. Help / an opinion from an admin (en-WP or (ideally) en-WP and commons) would be appreciated. Thanks. EdChem (talk) 00:04, 19 April 2017 (UTC)

Heptamethine dyes[edit]

Hi, I wonder if some editors more familiar with chemistry articles could take a look at Heptamethine dyes, this articles appears to me to be a promotion piece for one research group that is active in this area. It relies heavily on reference to one of their papers. I'm not sure it meets WP:GNG and could be worthy of AFD but I want to see what others here think. Thanks Aloneinthewild (talk) 11:28, 23 April 2017 (UTC)

I am not expert on the topic, but the article appears to be hype job of some narrow area. Indocyanine dyes are widely used in medicine (13535 hits), the vast majority (13212 hits) of citations involving Indocyanine green, for which we have a respectable article. Heptamethine dyes, the topic in question, is the subject of 40 hits, none of which are heavily cited. No review has been written. Aside from the tone of the article, a WP:COI aspect is indicated by one of the X-ray figures, which is sourced as "This is a photo of an xray overlaid with a heptamethine dye in mice. They have sent me an email allowing me to publish it under the heptamethine dyes section." My advice would be to take the article back to bare bones where it defines a heptamethine and makes brief mention of the currently cited literature. Probably some violations of WP:MEDRS. --Smokefoot (talk) 14:05, 23 April 2017 (UTC)

Notability of chemicals?[edit]

It's been awhile since I've checked into this topic, but how do folks here normally assess WP:GNG of a chemical? For the biology end of things we have WP:SPECIESOUTCOMES, but I haven't seen anything equivalent for chemicals. I'm currently figuring out what to do with 2-Decenedioic acid with the problem being that it really gets no mention in sources, and the only thing that really comes up are old primary journal articles that briefly mention it's found in royal jelly in lists or tables. Basically, not enough to warrant even the current unsourced sentence from a WP:WEIGHT perspective, and barely worth mention if at all at the royal jelly article. Would folks think this in an article for deletion territory, or there some other standard used for chemical stubs like this like having a CAS number to fill out the infobox at least? Kingofaces43 (talk) 05:05, 26 April 2017 (UTC)

What we have in that article is hardly worth having. But 2-Decenedioic acid appears to be a notable topic in that many independent authors have written on the topic, and been referenced by others. So we don't have the situation of one author pushing an idea that is not recognised by anyone else. There are also reviews: "The biological significance of ω-oxidation of fatty acids" by Yoshiro MIURA; and Contribution of of less chemistry focus: "Lipids in Honeybee (Apis mellifera) Royal Jelly to Health" Xing'an Li, Chaoqun Huang, and Yunbo Xue. And the artcle should reference SOME CARBOXYLIC ACIDS PRESENT IN ROYAL JELLY by William H. Brown, Robert J. Freure. It should definitely appear in the table in Dicarboxylic acid#Unsaturated dicarboxylic acids. added Graeme Bartlett (talk) 05:38, 26 April 2017 (UTC)
And having a CAS number is certainly not enough to warrant an article. We should be able to apply WP:GNG, but extend it to two different authors writing on the topic and not just one person who then references herself. I don't think that we want to be like species and say that if someone claims it exists, we can have an article on it. It gets even worse with fossils, as the evidence then is even more tenuous. Sometimes even if a chemical does not exist, it can have an article, eg NF5. The advice for students could also include what chemicals are worth writing about. Graeme Bartlett (talk) 05:45, 26 April 2017 (UTC)


Our acetylide defined this group as HC2-, but now someone changed it to C22-. The Goldbook says that it can be either, but with an electropositive metal attached: Acetylides: "Compounds arising by replacement of one or both hydrogen atoms of acetylene (ethyne) by a metal or other cationic group. E.g. NaC≡CH monosodium acetylide. By extension, analogous compounds derived from terminal acetylenes, RC≡CH."

I propose that we accept IUPAC's definition, remove the chembox since the anions themselves are not covered (anyway such carbanions do not exist without a covalently attached metal). Comments are welcome. --Smokefoot (talk) 14:56, 29 April 2017 (UTC)

I indeed don't like covering ions as independent chemicals (though the anion can have sufficient notability). Just wondering, would one be able to make an ammonium or phosphonium acetylide (tetramethylammonium, tetrabutylphosphonium or the like)? --Dirk Beetstra T C 16:29, 29 April 2017 (UTC)
OK, I'll probably proceed in removing the box. I also dont understand the point of a chemboxes for most ions.
Regarding the chemistry question, I dont think that one can make quat salts with highly basic anions, but I do not know the cut-off pKa. R4P+ forms phosphoranes with OR-, F-, and anything approaching a carbanion. R4N+ suffer Hofmann elimination even with hydroxide for R = Et or longer. R = Me resists degradation indicated by the fact that Me4N+F- is the unique quat fluoride that can been isolated in anhydrous state. --Smokefoot (talk) 17:27, 29 April 2017 (UTC)
Bis(tetrabutylammonium)acetylide appears to be known.[1] Trialkylammonium acetylides are believed to exist in equilibrium as transient intermediates in the Cacchi coupling reaction and Sonogashira–Hagihara coupling reaction.[2] An extensive attempt to synthesize tetramethyl or guanidinyl acetylides (I *think* they were aiming for mono not bis) did not succeed.[3] DMacks (talk) 03:11, 30 April 2017 (UTC)


  1. ^ Used on page 20 of Woltermann, Christopher J. (1996). Part 1: Studies of Synthesis of Mono- and Dinitroacetylenes, Acetylenic Nitrites and Nitrosoketenes (Thesis). The Ohio State University. 
  2. ^ Bruckner, Reinhard (2001). "13.3.4 Alkenylation and Arylation of Copper Acetylides". Advanced Organic Chemistry: Reaction Mechanisms. Academic Press. pp. 535–538. 
  3. ^ [1]
Great catches, maybe my internal guidelines are messed up. Bu4N+C2R would indeed be useful reagents. --Smokefoot (talk) 12:48, 30 April 2017 (UTC)
SciFinder couldn't find any tetraalkylammonium acetylides or tetraalkylphosphonium acetylides. Lots of false-positives though (tetraalkylammonium/phosphonium salt of other anionic sites in alkyne-containing molecules). DMacks (talk) 20:46, 30 April 2017 (UTC)
@Smokefoot: Here's a fun one: an atrane[1][2] intermediate. DMacks (talk) 04:02, 1 May 2017 (UTC)


  1. ^ secondary ref: Vedejs, Edwin; Denmark, Scott E. (2016). Lewis Base Catalysis in Organic Synthesis. 2. Wiley. p. 262. ISBN 9783527336180. 
  2. ^ ...which cites: doi:10.1021/jo9012332

I think this may have been my fault; my reasoning was while the page defined acetylide as HC2- Category:Acetylides contains only examples of MC≡CM species. To be frank the page needs a through re-write, the chemistries of HC2-, RC2- and MC≡CM are all jumbled together.--Project Osprey (talk) 22:03, 29 April 2017 (UTC)

At one time I duplicated the chembox, to make "ionbox" but it was not really a good idea. I think we can use for chembox for ions, as long as the article is just about the ion. If it is about a family of compounds, then chemboxes are not the right thing to use. A table of info can show information for several non-notable substances in the family. Graeme Bartlett (talk) 07:16, 30 April 2017 (UTC)
Thanks for all the input, the main thing is that I need to get started, everyone is welcome to revert or do their bit.--Smokefoot (talk) 12:48, 30 April 2017 (UTC)

Alkynation vs alkynylation[edit]

OK, in the process of reworking acetylide, I moved alkynation (sounds real enough, but forty some hits on CAS) to alkynylation, which has thousands of hits on CAS. I assume they are the same thing. --Smokefoot (talk) 17:05, 30 April 2017 (UTC)

Cyclic microcellular foaming[edit]

If you have time, can someone please take a look at Cyclic microcellular foaming? It is looks a little bit like spam to me.

The images are nice, the article is on a "minor" journal, cited 13 times in 4 years I guess the concept can be cited in some other article but an entire wikipedia article describing the publication is IMHO excessive. It is not my field, if someone else has the will and expertise (s)he can recycle and downsize the information (especially some of the images, they seem nice) somewhere else, and than propose a deletion? I am just saying, I don't know how to evaluate this field.

The authors User:Questpr and User:Gandhi.iitdelhi also created Nucleation in microcellular foaming

I try to improve the categorization of the related files on commons.--Alexmar983 (talk) 15:29, 1 May 2017 (UTC)


Is that really the correct spelling, with one l instead of two? Clayden, Greeves, and Warren (2nd ed.) have it with two l's on p. 1076. Double sharp (talk) 15:22, 2 May 2017 (UTC)

That is a recurring question. Here're the data from Chem Abs:
  • "metallation" → references (817) of which 51 are reviews, only one well cited (239 cites)
  • "metalation" → references (16547) of which 876 are reviews, at least 10 of which are cited >500x each, including those by Snieckus, Fu, van Koten, and other leading scholars. Here is one example in the title: "Directed ortho metalation.  Tertiary amide and O-carbamate directors in synthetic strategies for polysubstituted aromatics" Snieckus, Victor

From Chemical Reviews 1990, 90, 879-933.

So the experts think that it is one l. --Smokefoot (talk) 20:22, 2 May 2017 (UTC)

Thanks; good to know! Perhaps we should mention a little bit about the variant spellings in the article, so that the question recurs less often? Double sharp (talk) 23:03, 2 May 2017 (UTC)
OK I just changes all of them that were not part of an article's title
Thank you! Double sharp (talk) 02:48, 3 May 2017 (UTC)
Illustration of silylmetalation in the carbometalation article

While we are on the carbometalation article, I noticed the image File:Silylmetalation.png, shown at right and uploaded by V8rik in 2007. The image has, in red:

  • ZnCl for what I am guessing is meant to be zinc chloride
  • two species with zinc centres shown with negative formal charges, Zn2−

And in addition:

  • issues with charge balance
  • it appears that the deprotonated 2,2'-dihydroxybiphenyl and tert-butyl ligands on the zinc centre appear to disappear to be replaced with methyl groups (I know this is not the intended meaning, but to a non-chemist it could be confusing).
  • where did the H's on the 2,2'-dihydroxybihenyl go when it became an anion
  • tert should be italicised, so t-Bu or more commonly tBu, I think, rather than t-Bu
  • it appears that the MgCl
    has a charge, as MgCl+
  • A 2M+
    , which I think is meant to be a Cu+
    and a Li+
    , and makes me wonder why the MgCl
    (with or without charge) vanishes but the Li+
    remains and the CN
    and Br
    don't appear either like the cations do

I'm wondering if there are other things editors want to suggest be changed, and whether V8rik or another editor can provide a replacement. Thanks. EdChem (talk) 10:20, 3 May 2017 (UTC)


Can we delete the chembox in Nascent_hydrogen ? This is not a chemical compound but a chemical concept for reactive hydrogen which is now deprecated. Having a chembox with data for hydrogen creates confusion. Snipre (talk) 08:58, 5 May 2017 (UTC)

Yes, delete it, the names in the chembox are a bit of a give-away as to who put it there --Project Osprey (talk) 10:00, 5 May 2017 (UTC)
Although one of the most enthusiastic deletionists, I wonder if we shouldn't keep but make sure that its tone is disparaging. We have a full article on Flat Earth. Someone is going to create this thing again, so we might as well have something sitting there that makes clear that it is a junk concept. To keep the conversation going, I removed most of the article. Feel free to revert or redo my action. --Smokefoot (talk) 10:35, 5 May 2017 (UTC)
My concern was just about the chembox which was filled with data and identifiers for molecular hydrogen. But I think the article should be kept: we just have to focus on the concept and not on the chemical. Snipre (talk) 11:09, 5 May 2017 (UTC)

I agree completely that the article should be kept, but needs to make absolutely clear that the concept is deprecated. Changes are needed to the article Nascent state (chemistry), too. Smokefoot's trimming of the article is drastic but justified. I'm looking into seeing what I can add that is in line with the actual topic. EdChem (talk) 11:51, 5 May 2017 (UTC)

  • I've started adding some history. Searching in Google books, however, there are some decidedly odd recent book sources that take nascent hydrogen seriously like: [2] and [3] and [4] – on this last one, I wonder if the term has come to have a meaning in engineering? EdChem (talk) 13:17, 5 May 2017 (UTC)
@EdChem: I think one could conclude that that last text took a pragmatic approach to simplifying the explanation chemistry of hydrogen embrittlement at the cost of accuracy. Defensible, maybe, given the potential repercussions of improper material selection of alloys for high-temperature hydrogen service, but I wouldn't infer any special meaning in engineering at large based on it. VQuakr (talk) 23:07, 6 May 2017 (UTC)
Thanks for the explanation, VQuakr. Hydrogen embrittlement is certainly a problem, though I agree it can be described / explained without invoking the nascent state. EdChem (talk) 17:32, 14 May 2017 (UTC)
  • Looking at the two references you have you'd think the term has meaning in passing official chemistry tests in India. The kids over there are not to be envied. (I've seen the term in the context of the Langmuir torch. (talk) 22:48, 6 May 2017 (UTC)
  • The history of the concept is recapitulated in Bull. Hist. Chem. 1990, 6, 26-36, online here [5] and here [6]. That review should allow to get rid of most of the references to primary literature. (talk) 20:25, 5 May 2017 (UTC)
  • Nascent state (chemistry) still has the same old rubbish in it that used to be in nascent hydrogen. Would someone help out?! (talk) 22:49, 6 May 2017 (UTC)
 Done I think I've got it historically-focused now. VQuakr (talk) 23:02, 6 May 2017 (UTC)
Well done. Now you have two parallel articles on the same subject, a concept of only historical interest. (talk) 14:50, 7 May 2017 (UTC)
Ok, then we are agreed to merge these articles into Nascent state (chemistry)??--Smokefoot (talk) 15:08, 7 May 2017 (UTC)
Fine with me. I'm not hung up on the title. (talk) 15:47, 7 May 2017 (UTC)
Meh. The two subjects together are never likely to need to be separate for purely length reasons, but the focus of Nascent hydrogen is currently more on, well, hydrogen. I am unconvinced that it is editorially favorable to merge them. VQuakr (talk) 18:28, 7 May 2017 (UTC)
I concur with VQuakr, the idea of the nascent state is applied to substances other than hydrogen, the Bull. Hist. Chem. paper mentioned above talks of nascent oxygen and nascent chlorine, IIRC. I suspect hydrogen is the only element that is due a separate "nascent ELEMENT" article, but I do think the content is better separating the idea of the state from the specific example of hydrogen. EdChem (talk) 17:32, 14 May 2017 (UTC)

Hover text[edit]

We are missing hover text, probably after making whole cells clickable. Example: Template:Extended periodic table (by Fricke, 32 columns, compact). --Obsuser (talk) 03:28, 6 May 2017 (UTC)

With me they show OK. That's Firefox here, in a desktop view. To be clear: when hovering a cell with the mousepointer in the periodic table, we expect a mouse-tooltip appearing: cell "I" shows tooltip "Iodine" (which is simply its wikilink target page). Just as we expect this for any wikilink in text. CSS-formally this is called the 'title' btw. -DePiep (talk) 13:50, 8 May 2017 (UTC)
@DePiep: Thing is that there are no hover descriptions when you move cursor from the link itself to the field: for example "Beryllium: alkaline earth metals; primordial; solid". Compare 121 and 124 in {{Extended periodic table (by Fricke, 32 columns, compact)}}.
Or it was intentional because iodine link was too narrow? --Obsuser (talk) 17:25, 16 May 2017 (UTC)
Yes a few months ago we made the whole cell click-sensitive (while showing the wikilink regular). It was searched for the small "I" (iodine) character, but applied to all element cells. With this, the tooltip (css-title) shows when the cell is hovered -- at least, intended & expected & ok with me here.
With Be I get css-title "Beryllium" (but not its properties you listed). With E121 "Unbiunium" OK. But E124 is not linked, and only says property "(superactinide)" (This is a bit weird agree, but not the issue here).
So, looks like the problem is still: I cannot reproduce the bug you describe. How does {{Periodic table}} function for you? (with me: OK too) -DePiep (talk) 18:39, 16 May 2017 (UTC)
Big ones are good, this one that I was complaining about and maybe some similar if eongf oist are not (it is "weird" i.e. has no consistency, properties are not shown). Not a big issue, small one, like a suggestion. --Obsuser (talk) 19:24, 19 May 2017 (UTC)
If it does not work as intended ... it is relevant ;-). What browser are you using? Does the error happen on desktop screen, or in mobile view? -DePiep (talk) 21:51, 19 May 2017 (UTC)

BR vs WBR separator usage in Chembox[edit]

Hi, there were many occurrences of single IUPAC name (IUPACName=...) split by <br> (in order to pre-split the long name to fit it in the box obviously), however the side-effect was that it was interpreted as multiple IUPAC names in the Chembox. So I took the initiative of replacing the <br>'s that were meant such way, to <wbr>'s, according to WP:LINEBREAK, and because

  1. at least two major web browser that I was checking, were auto-splitting long words containing hyphens without problems,
  2. Wikipedia is served as html(5) doctype, so the <wbr> usage should be without problems as well.

Mykhal (talk) 23:53, 6 May 2017 (UTC)

Great edits, that's the tag I was searching for all those years. I hope it does not copy/paste and that you had an eye for true newlines (for starting a new name). -DePiep (talk) 13:53, 8 May 2017 (UTC)
Of course I had to be careful, and I did try hard not to brute replace all BR's (e.g. this edit). That's also why I did not yet try to learn to write editing bots. —Mykhal (talk) 19:30, 8 May 2017 (UTC)
I did not look at your edits. You say you did not even use AWB? -DePiep (talk) 20:47, 8 May 2017 (UTC)
I don't know what AWB is. I have used google search query: "iupac names" -"iupac name" SMILES OR "InChI", so I got many false positives. But I think I have sifted through and edited all resulting pages. —Mykhal (talk) 18:48, 9 May 2017 (UTC)
Mykhal, I can categorise every article that has a <br> in |IUPACName=. Would that help? -DePiep (talk) 21:27, 8 May 2017 (UTC)
There are not so many such articles based on insource:/IUPACName *=[^\|]{3,50}\<br/. Most of the hits are false-positives. --Leyo 22:04, 8 May 2017 (UTC)
Thanks for the regex. Your search gave 112 hits. With insource:/IUPACName *= *[^\|]{3,50}\< *br I got 499 hits. (But why false positives like Antimony tribromide btw?). -DePiep (talk) 21:44, 9 May 2017 (UTC)
The closing / is missing. --Leyo 07:39, 10 May 2017 (UTC)
The "false positives" are cases when multiple names are used, and cannot be distinguished reliably from those artificially inserted possible word breaks without advanced artificial intelligence, like human brains. It can be done unreliably with some assumptions e.g. that a name beginning is /(\d+(,\d+)*-)?[A-Z]\w/ after BR —Mykhal (talk) 20:15, 14 May 2017 (UTC)

Moving identifiers out of the infobox: WP:MED in action[edit]

Infoboxes {{Chembox}} and {{Drugbox}} are long with much data that is maybe not in the best place there. Over at WP:MEDICINE a similar problem is approached in an RfC, by creating a separate "Resources" box way below on the article page. Could be inspiring. -DePiep (talk) 15:45, 8 May 2017 (UTC)

To me that is still a strange thing to do. I use the identifiers to get to more data (especially if I don't trust physical data on Wikipedia). I'd prefer that in the top. We're (still) not a reliable source. --Dirk Beetstra T C 16:10, 8 May 2017 (UTC)?
TBH, I think the identifiers should not be placed so highly, since they are all external links (while I do appreciate the "jump to more data" opinion). --Izno (talk) 16:28, 8 May 2017 (UTC)
There is nothing against external links in infoboxes, many carry them (though we do linkfarm, relatively speaking). I do have sympathy for the 'authority control'-type of linking as well, which is not a bad option. It is just .. I use these links sometimes to verify whether the Wikipedia numbers are OK (I don't always trust Wikipedia) .. gets a bit of a down-and-back-up action if they are at the bottom. --Dirk Beetstra T C 17:15, 8 May 2017 (UTC)
A wp:infobox really should be a summary of the article, and we in chemistry can add the melting and boiling points reasonably. But those coded-ID external links are not really lead-infobox level info. Quite telling: by Wikipedia design, the infobox is the first show especially in mobile view (see aspirin in aspirin (mobile view)). Not every reader has preferences like Dirk, Dirk ;-). IMO we really could use a section 'data sheet' for chemicals. -DePiep (talk) 20:43, 8 May 2017 (UTC)
Identifiers such as CAS numbers are lead level material and absolutely belong in the infobox. Many readers, myself included, have a preference like Dirk's. The problem with the mobile view is that that portions of the navbox cannot be collapsed. I have made a proposal to fix that here. Boghog (talk) 03:04, 9 May 2017 (UTC)
The CAS number for infobox is not the best example (it's the easiest 'yes'). Same for melting point. But issues arrive with the dozens of other identifiers and properties. These are properties we surely expect in a 'datapage' section, but not in the lede/infobox top.
About collapsing infobox sections (never in mobile view): there is a reason for that omission. It has to do with webpage design & usage (note: not just Wikipedia page design then). In short: if it is unimportant enough to collapse&hide, then it need not be there. And I can understand your "Dirk's" preferences, but we editors are not representative for our readers. -DePiep (talk) 21:32, 9 May 2017 (UTC)
I understand that we are not (necessarily) representative for our readers. That is why the WP:MED decision surprises me, the editors there made the decision to move the identifiers to the bottom of the article, based on their preferences within the project. Then when the exact placement was questioned (where at the bottom), a global discussion was started. I, who is more a reader of medical articles, suggested to .. keep them in the infobox.
I also go with Boghog's additional argument that some of the identifiers are lead-level material. And please don't let us get the idea to move all but three to the bottom of the page. --Dirk Beetstra T C 03:08, 10 May 2017 (UTC)
The assertion that collapsed navboxes should not be used in mobile is nonsense. Many, many mobile phone apps make effective use of collapsed information that can quickly be uncollapsed to reveal more detail. This is a glaring omission in the Wikipedia mobile view that needs to be rectified. I am only proposing that the infobox be collapsed in the mobile view, not in the desktop view. Furthermore the problem with navboxes in mobile view is not only due to the identifiers section, but other sections as well. Because of their large size, infoboxes overwhelm small screens. One has to scroll down quite a ways to get to the lead. On the desktop, a large infobox is much less of an issue. This is especially true of articles with a long table of contents where the navbox can effectively use otherwise wasted space to the left of the table of contents. Boghog (talk) 05:09, 10 May 2017 (UTC)
Sections of articles starting with the second section in the Mobile view are collapsed. Why is it OK to collapse article sections and not navbox sections? Boghog (talk) 10:06, 11 May 2017 (UTC)
My take: section titles this way are the TOC. Is the main navigation for a page. Collapsing parts of a box does not fit this reader perception. I guess it is undesired to use the mobile screen with more than a few zoom-levels, because the reader might loose overview ('where am I?'). Assuming our page-designers do not want to add that show/hide option, my suggestion nicely does use-section-to-collapse by creating a section "==Data sheet==". Also fits with my idea that not all data is important enough for the top infobox. -DePiep (talk) 10:39, 11 May 2017 (UTC)
Yes, the section titles in the mobile view are the TOC. For consistency, it would also make sense to collapse all the sections of the infobox. The section titles within the infobox would then provide navagation within the infobox. Even if one moved all the identifiers out of the infobox (which I think is a really bad idea), many infoboxes would still overwhelm the lead in the mobile view. Allowing the option of collapsing sections of the navbox fixes this problem. One could even make the case that infobox sections should be collapsed by default. Boghog (talk) 11:18, 11 May 2017 (UTC)

EU classification (DSD) will soon cease to be in force[edit]

Please see Wikipedia talk:Chemical infobox#DSD data but no GHS data for more details and task that need to be done. --Leyo 22:17, 8 May 2017 (UTC)

Another round of student additions?[edit]

I think I might have found a bunch of new pages created as some sort of student assignment. The properties seem to be as follows:

  • New editors with no userpages who created new articles on 21 April and have edited only those pages
  • Pages added either in one go or in a flurry of edits over a couple of days

At first glance most of these pages seem to be ok but I have to admit I haven't gone through them carefully. However, unless there are just 7 people in this class I'm clearly missing some. --Project Osprey (talk) 14:26, 9 May 2017 (UTC)

Page name Creation date Creator
Organotantalum chemistry 21 April User:Bhuffmanscripps
Nickel(II) precatalysts 21 April User:Samantha.green403
Chemical bonding of H2O 21 April User:Holmescallas
Cobalt(II)–porphyrin catalysis 21 April User:Deadpan07
Mukaiyama hydration 21 April User:Solosh11
Stannatrane 21 April User:J.derosa
Moroidin 25 April User:Momast017

I am very pleased with this find, new content! V8rik (talk) 17:27, 9 May 2017 (UTC)

Yes, we are graduate students and this was an assignment for our organometallics course. Each page was peer-reviewed by two other students in the class. Solosh11 (talk) —Preceding undated comment added 02:49, 10 May 2017 (UTC)

New homework essays by kids with weak perspectives and reliant on primary, mainly US sources, but we can anneal these things over time. Unfortunately, their teachers are probably not very involved. --Smokefoot (talk) 16:12, 10 May 2017 (UTC)
Certainly better contributions than those other recently created stubs. Graeme Bartlett (talk) 10:24, 11 May 2017 (UTC)

And again[edit]

Another round of new pages and large expansions Wikipedia:Wiki Ed/Dartmouth College/The Chemistry of Macromolecules (Spring 2017). --Project Osprey (talk) 12:08, 16 May 2017 (UTC)

And still more[edit]

Wikipedia:Wiki_Ed/Hunter_College/Chemistry_378_(Spring_2017), taking on gigantic topics. Not very promising. Instructor basically missing in action.--Smokefoot (talk) 14:25, 22 May 2017 (UTC)

Not just gigantic topics but in gigantic numbers... 98 students! (am I reading that correctly?) that must be some kind of record for us. --Project Osprey (talk) 14:43, 22 May 2017 (UTC)
The edits from this course I've encountered on watchlist are virtually all nuke-on-sight bad. It's as if they had no training or resources about the basics of what WP is and how articles and subarticles are structured. DMacks (talk) 19:59, 22 May 2017 (UTC)

Cyclopropenium ion[edit]

Will someone please take another look at Draft: Cyclopropenium ion? A reviewer is currently looking at it. It appears to be the work of one person who has not been working on anything else. Robert McClenon (talk) 16:39, 15 May 2017 (UTC)

Also, will someone please review Draft:Hydrogen-bridged cations? These may be two papers from one class, since they both have to do with distributed positive charge. Robert McClenon (talk) 16:46, 15 May 2017 (UTC)
Notice that almost all the artwork in Hydrogen-bridged cations looks copied (to use the polite term). Please do not accept.--Smokefoot (talk) 16:53, 16 May 2017 (UTC)
Are Cyclopropenium ion and Cyclopropene the same thing? There is a confusing web of redirects to and from apparent synonyms between these two articles (use "What links here" to find them) Some cleaning up, if not an merge, is probably needed to straighten out the various links. I'm afraid as the accepting reviewer of "Cyclopropenium ion" I may have contributed to the tangle. Roger (Dodger67) (talk) 17:00, 15 May 2017 (UTC)
User:Dodger67 - No. Cyclopropene and Cyclopropenium ion differ by one electron, and that does make a difference. Cyclopropene is a neutral compound. Cyclopropenium has lost an electron and is positively charged. The charge is delocalized, and for complicated reasons that increases its stability. But they are closely related. Robert McClenon (talk) 15:21, 16 May 2017 (UTC)
talk - Incorrect. Cyclopropene has the formula C3H4, Cyclopropenium ion usually refers to cyclopropenium cation, with the formula C3H3+. --Smokefoot (talk) 16:53, 16 May 2017 (UTC)
My error. That is what I meant, but they differ by a proton and two electrons. Robert McClenon (talk) 05:39, 17 May 2017 (UTC)
These are homework assignments (unsupervised forced labor that produces a crappy essay that impresses editors who know little chemistry). Ideally such articles should not be accepted until Chemistry project reviews them, please do that next time! --Smokefoot (talk) 17:11, 15 May 2017 (UTC)
Smokefoot Unfortunately AFC can't force WikiProject Chemistry members to register as AFC reviewers. The lack of topic specialists doing regular (read "constant") AFC and NPP work is a perennial problem. Roger (Dodger67) (talk) 17:34, 15 May 2017 (UTC)
Well, thanks for checking. I and some colleagues here experience a mixture of joy and anger about these things. On one hand they usually contain valid content, often on topics we welcome, on the other hand they are often poorly constructed and ultraspecialized. Many of us editors feel sudden pressure to make them semi-respectable so that they do not embarrass our project. Cheers, --Smokefoot (talk) 18:47, 15 May 2017 (UTC)
  • I am less pessimistic about class projects, they can grow into quality articles. Cyclopropenium ion is one of them. Remember these are highly specialized topics but they serve a purpose. V8rik (talk) 20:52, 15 May 2017 (UTC)
Draft articles can be spotted along with other new chemistry page creations in User:AlexNewArtBot/ChemistrySearchResult. It updates about 1900 UTC each day. But what are our standards? Essential is no copyright infringement or promotional content. I don't like seeing one liner substubs saying "xyz is a chemical." It is good to have a suitable name, chembox, categories, section headings, wikilinks, talk page with project marked, and definitely factual correctness. Much harder is to improve the quality of references. In the case of Cyclopropenium ion it was originally misleading us in the lede to believe that this ion exists, when only derivatives are known. Graeme Bartlett (talk) 07:52, 16 May 2017 (UTC)
User:Graeme Bartlett - Not directly on the subject of chemistry in sensu stricto, but on the subject of whether the subject exists, I have also been seeing articles on proteins which, it appears from reading, are only predicted based on the DNA. Robert McClenon (talk) 15:30, 16 May 2017 (UTC)
We can certainly have articles on things not yet proven to exist, but it should be clear in the first sentence of the article! Graeme Bartlett (talk) 21:24, 16 May 2017 (UTC)

Chemicals derived from petroleum - request[edit]

Hi. I have looked a few times within WP for content discussing industrial production of chemicals and where precursors come from. What has led me there are edits like this that pretty clearly derive from chemophobia.. with which I did this, btw).

I have looked a few times for sourcing to add content to Azo compound about how petrochemicals are used as starter stock (or I guess article-wise precursors) for industrial production and what goes on afterwards... practical nuts and bolts stuff that anybody could understand, including the high-level economics of it, but not found anything useful. Would be great if somebody who knows the literature could add content about that... with respect to azo dyes in general but everywhere, really. We often lack this kind of concrete content about how things are actually made and why they are made that way. Please consider! Thx Jytdog (talk) 17:24, 15 May 2017 (UTC)

It would be great if such information were readily available, but often this information is held as trade secrets by the manufacturers. Nevertheless, there seem to be several promising sources, for example:
  • Weissermel K, Arpe H (2003). Industrial Organic Chemistry Important Raw Materials and Intermediates. (3rd ed.). Weinheim: Wiley-VCH. ISBN 978-3-527-61459-2.  Boghog (talk) 17:52, 15 May 2017 (UTC)
Or: Kirk-Othmer Encyclopedia of Chemical Technology, 27 Volume Set, 5th Edition (2007) ISBN 978-0-471-48494-3 and Ullmann's Encyclopedia of Industrial Chemistry. JimRenge (talk) 18:05, 15 May 2017 (UTC)

Draft:Electrochemical Promotion of Catalysis (EPOC)[edit]

Please review. Robert McClenon (talk) 03:14, 17 May 2017 (UTC)

YesY accepted. Graeme Bartlett (talk) 04:18, 17 May 2017 (UTC)
Looks pretty weird to me. Indicators from the lede:
  • Begins with emphasizes on (an obscure - non-wikilinked) individuals vs the topic at hand, i.e. promotional "The EPOC effect was firstly discovered by M. Stoukides and C. Vayenas in the early 1980s and ...."
  • Emphasizes research and semi-quantifies numbers of impacts "....have been widely studied by various research groups for more than 100 heterogeneous catalytic reactions of mostly gaseous molecules.[1]"
  • Tells the reader that the topic is important vs letting the topic speak for itself "...The EPOC effect has been evaluated as an important phenomenon which can closely link electrocatalysis and thermal catalysis.[2][3]"
And my old favorite - absence of WP:SECONDARY reference. For articles on phenomena, a review or textbook is almost obligatory.
--Smokefoot (talk) 12:36, 17 May 2017 (UTC)
It strikes me that refs 2 and 3 are reviews. What annoys me is the lack of neutral tone, all versatile and important phrases should be removed. V8rik (talk) 17:10, 17 May 2017 (UTC)

Popular pages report[edit]

We – Community Tech – are happy to announce that the Popular pages bot is back up-and-running (after a one year hiatus)! You're receiving this message because your WikiProject or task force is signed up to receive the popular pages report. Every month, Community Tech bot will post at Wikipedia:WikiProject Chemistry/Popular pages with a list of the most-viewed pages over the previous month that are within the scope of WikiProject Chemistry.

We've made some enhancements to the original report. Here's what's new:

  • The pageview data includes both desktop and mobile data.
  • The report will include a link to the pageviews tool for each article, to dig deeper into any surprises or anomalies.
  • The report will include the total pageviews for the entire project (including redirects).

We're grateful to Mr.Z-man for his original Mr.Z-bot, and we wish his bot a happy robot retirement. Just as before, we hope the popular pages reports will aid you in understanding the reach of WikiProject Chemistry, and what articles may be deserving of more attention. If you have any questions or concerns please 0contact us at m:User talk:Community Tech bot.

Warm regards, the Community Tech Team 17:16, 17 May 2017 (UTC)

This tool provides very useful information that helps guide article improvement. Many readers and editors are grateful for these efforts.--Smokefoot (talk) 18:56, 17 May 2017 (UTC)
Should we consider upgrading importance on article with a lot of readers (on a permanent basis)? Graeme Bartlett (talk) 11:13, 18 May 2017 (UTC)
Might be worth looking at the popular articles that are not standard chemistry content for accuracy. For example, number 2 on the list (with approaching 10k views day−1) is BODIPY. Its synthesis image (File:BODIPY synth.png) was uploaded in 2008 by Ph0987, who has only made one edit since 2014 and only four edits since 2012, and the image has an error. The second synthesis should show ArCOX as the reagent to match the aryl group in the product and the text, but for some reason reads RCOX. This article has seen little editing – eight edits in the last four years for these cumulative changes – and I'm not sure where all the traffic came from on 3 and 4 April (~274 000 views) but in general articles getting substantial sustained traffic are likely worth some attention. I'm not convinced that more traffic means more important as a chemistry topic, though. EdChem (talk) 13:41, 18 May 2017 (UTC)
Massive number of views over a couple of days only suggests some automation out of control. But if it sustained viewing it would be more human interest. Graeme Bartlett (talk) 21:17, 19 May 2017 (UTC)

Request corrections in diagrams[edit]

Illustration of silylmetalation in the carbometalation article

In the above thread on carbometalation, I noted some issues with the image File:Silylmetalation.png, shown at right and included in the carbometalation article. It was uploaded by V8rik in 2007. It has, amongst other issues:

  • ZnCl as the formula for zinc chloride
  • zinc ions with formal negative charges
  • what could be taken as a magnesium(III) centre in MgCl+
    , amongst other issues
  • a potentially-confusing disappearance of ligands around the zinc centre, replaced by bonds which are meant to imply connection to what was there, but which could be taken as methyl groups
  • issues with charge balance
  • some species disappear (like the protons on the 2,2'-dihydroxybiphenyl) but others are preserved (like the Li+)... either have everything unneeded disappear, or show everything, but the combination of both can be confusing
Synthesis of dioscorine from trigonelline

I have also noticed that the File:Highlights of the synthesis of dioscorine from trigonelline.png has mistakes in it. It was uploaded by Renaureal who also wrote the dioscorine article, and has not edited since that day in 2015. According to the article text, the source paper for the diagram is doi:10.1016/0031-9422(88)83019-X and the issues I see include:

  • the arrow-pushing is clearly wrong in both cases where it is used:
    • in the first, the Michael addition (which is missing its base) shows breaking of C—C bond from the reactant where actually the base would deprotonate the acidic hydrogen alpha to the carbonyl and carboxylic acid, which is then the nucleophile that attacks the aromatic ring
    • in the second, the arrows show the formation of product with an oxygen atom surrounded by four double bonds and a lone pair! The bond forming reaction should be from the ring to the carbonyl carbon to form an alcohol moiety (after protonation) and a bridge-head.
  • the product of the decarboxylation step has lost two carbons...
    • the methine (technically a methanetriyl) to which one of the carboxylic acid groups is attached should become a methylene, but instead it disappears only to reappear in the subsequent structures (ie. the β-imino acid has N—ring methine—methine α to carboxylic acid—ketonic carbon... after decarboxylation, this should become N—ring methine—methylene—ketonic carbon but instead becomes N—ring methine—ketonic carbon
    • the methyl side chain on the alkene disappears and then re-appears
  • the species labelled as an imino acid is actually not an imino acid, having no C=N moiety
  • the product from the second set of arrow-pushing should have a C=C bond and a C=N+ bond in the ring system, but the C=C bond has been hydrogenated (somehow) to a single bond
  • the arrows going to the dumetorine side product (found in the yam Dioscorea dumetorum): the first is unlabelled, the second reads "Further" and "lactone formation", but the second step is lactone formation and nothing else. I suggest the first arrow read something like "hydrogenation (multiple steps)" and the second read simply "lactone formation" or "lactonisation."
  • the arrow leading to dioscorine product reads "Reaction of iminium ion with lactone", but actually the reaction produces a lactone and also involves reduction of the iminium ion to a tertiary amine. I suggest a label like "Reduction and lactonisation."

The dioscorine article is also not formatted along the lines typical of a chemical article (infobox etc) and has seen little editing since its formation. I haven't looked through it in any detail (I was adding links to catharanthine when I found it as part of a DYK issue, so any editing would be welcome. In addition, new versions of these two images are needed. Maybe not everything I have noted will be seen as a problem by other editors, but I do believe that some adjustment is necessary. Thanks. EdChem (talk) 23:23, 17 May 2017 (UTC)

V8rik has contributed so much but must have thick skin by now. So if a figure is flawed, I recommend moving it to Talk or removing it. Most readers, me included, look mainly at images and ignore text. So getting the images right is important. There has also been a trend toward keeping words out of images so that the resulting figures can be more useful in other language wikis. --Smokefoot (talk) 00:24, 18 May 2017 (UTC)
I looked at the Phytochem paper on the natural product. Here is a very simplified scheme. I think that we might spare readers of arrow pushing (which is kinda out of date anyway). But please advise while I have the artwork on my desktop. --Smokefoot (talk) 00:53, 18 May 2017 (UTC)
Smokefoot, on your diagram, the positive charge should be on the N and not the Me, there is a double bond in the reagent and intermediate missing, and this version gives no indication of the side reaction. EdChem (talk) 02:15, 18 May 2017 (UTC)
Improved image. If you really want the + next to N I can do that, but it is also common (as in NMe4+ to put charge next to alkyl). --Smokefoot (talk) 02:53, 18 May 2017 (UTC)
biosynthetic scheme
Smokefoot, thanks. The placement of the plus isn't that important. There is one thing that bothers me, though, and I notice it is in the original too... the stereochemistry of the alkene goes from (Z) to (E) for no apparent reason – would you please check if that happens in the paper (in which case we accept it, obviously), or whether the substituted hept-2-en-dioic acid had an (E) stereochemistry? Thanks. EdChem (talk) 03:59, 18 May 2017 (UTC)
OK this is more work than just drawing. I had assumed that you knew the structures. In any case, the attached is closely modeled after the Phytochem paper. --Smokefoot (talk) 13:52, 18 May 2017 (UTC)
This thread once again proves that peer review on chemistry images takes on average 10 years! I have reviewed the case and decided to remove the entire section. V8rik (talk) 17:34, 18 May 2017 (UTC)

Definition of Macrocyclic Ligand[edit]

I searched for a source how macrocyclic ligand is actually defined. In the wikipedia article there is the IUPAC Gold Book as a source. However, I didn't find a definition there for macrocyclic ligand. Neither in my downloaded pdf (Version 2.3.3, 2014-02-24) nor on the website Also in the Red Book I found nothing. So, does anyone have a source for a definition?

Wulfram G.T. (talk) 19:48, 21 May 2017 (UTC)

If IUPAC doesnt define it, then you'll need to do some work and use your judgement based on a collection of hopefully good books and reviews. If you haveaccess to a high quality technical library and an hour to spare, you can do this readily. If you dont have good library sources, then its Google-and-pray. I googled "macrocyclic ligand book" and found the book "Coordination Chemistry of Macrocyclic Compounds", which appears reasonably authoritative judging from the fact that one contributing author won a Nobel Prize. The book begins with a definition "a cyclic compound with nine or more members (including all hetero atoms) and with three or more donor (ligating) atoms." Examples in Wikipedia include TACN and 9-ane-S3. Not that it matters, but for me, macrocyclic ligands usually refer to tetradentates with ring sizes between 12 and 16. --Smokefoot (talk) 20:17, 21 May 2017 (UTC)

Please assess a new draft[edit]

See User:BeaglePower/sandbox, I'm not sure what to make of it. It seems to me that it covers several different aspects of acid-base chemistry, but my knowlege of the topic is rudimentary and rusty - high school was over 30 years ago. Roger (Dodger67) (talk) 20:02, 22 May 2017 (UTC)

  • It would be excessive to add this to Russell S. Drago which already has a summary of the topic(s). For this to become an article we really need secondary (review or book) references to show that the concepts are notable. It would go to an article titled ECW model or electrostatic and covalent parameters. Has anyone here ever heard of these concepts before? Graeme Bartlett (talk) 23:38, 22 May 2017 (UTC)
I have moved this to Draft:Electrostatic and Covalent Equation for now. If there is a better title, it can be moved again? Robert McClenon (talk) 02:00, 23 May 2017 (UTC)
The E-C equation is probably notable because Drago was prolific promotor. It was introduced in the spirit of Gutmann's Donor number, a result of the 1950's-1960's fascination with parameterizing (Lewis) acid-base reactions. Drago sought to extend the concept to coordination complexes. A huge fight broke out as this quantitative parameterization competed with Pearson's more qualitative HSAB theory. Gerold Schwarzenbach (der Prof at ETH, popularier of EDTA) was also involved. At least in the US, Drago was influential as indicated by his winning ACS's Inorganic Awd. The E-C equation was basically his life's work. I glanced at the article. It seemed way too long, but almost all articles seem that way to me. My 2 cents. --Smokefoot (talk) 02:17, 23 May 2017 (UTC)
Can it be accepted into mainspace it its current state, or do one of you topic specialists want to do a review? Roger (Dodger67) (talk) 12:07, 23 May 2017 (UTC)
OK, I shrunk it to 40% of the original and named it following Graeme's suggestion. See ECW Model. --Smokefoot (talk) 01:11, 24 May 2017 (UTC)

Also requesting the review of Draft:Kinetic isotope effect measurement at natural abundance, a draft that has been waiting for nearly 30 days. JTP (talkcontribs) 14:54, 25 May 2017 (UTC)

It appears as if the text of this draft has already been merged into Kinetic isotope effect. -- Ed (Edgar181) 15:02, 25 May 2017 (UTC)


Check out [list] for articles using the term "chirally". My guess is that it is not a word. If anyone has suggested alternatives, go for it. --Smokefoot (talk) 03:37, 26 May 2017 (UTC)

If the first page of hits is a representative sample, it's a valid word because it's used in titles of cited refs. "Chirally Correct" also appears to be some sort of marketting mumbo-jumbo for some cosmetics. DMacks (talk) 03:41, 26 May 2017 (UTC)
It's a word. It's the adverb formed from "chiral", which means "lacking mirror symmetry", and is used (in my experience) in chemistry, physics, and mathematics. The phrase "chirally correct" is also useful: for example, amino acids exist in laevo- and dextro- forms, with only the laevo- forms being nutritious, so a protein supplement containing dextro amino acids would be of little value, and "chirally incorrect". Marketing people can of course write any kind of bullshit. Maproom (talk) 07:50, 26 May 2017 (UTC)

Adept (insect growth regulator)[edit]

I'm not sure about the notability criteria for chemicals, so I was hoping someone from this Project could scan the article. At first glance, it may be too WP:PROMO thanks to the WP:PRIMARY sources. Nicnote • ask me a question • contributions 20:35, 30 May 2017 (UTC)

This article should be either redirected or merged into the existing article about the active ingredient in Adept, diflubenzuron. We generally don't have separate articles about the many different branded products that contain an insecticidal ingredient unless they are independently notable according to the general notability guideline, which doesn't appear to be the case here. -- Ed (Edgar181) 21:20, 30 May 2017 (UTC)
Agreed. It should be merged into diflubenzuron (not that there is a lot to merge), and redirected. ―Biochemistry🙴 21:42, 30 May 2017 (UTC)
Already done actioned by Octoberwoodland. Graeme Bartlett (talk) 23:56, 30 May 2017 (UTC)
Added to Adept (disambiguation). ―Biochemistry🙴 15:55, 31 May 2017 (UTC)

AcacH enol is C2v?[edit]

Is this figure from acetylacetone correct? I would ask on that talk page but this is an important compound.

Acetylacetone keto-enol tautomerism.svg

--Smokefoot (talk) 01:41, 31 May 2017 (UTC)

A π-bond involving a hydrogen atom? That's an interesting idea. Maproom (talk) 08:35, 31 May 2017 (UTC)
Not a theoretician, but pseudo-aromaticity seems to be a thing and has been invoked for acetylacetonates. [7] No, I don't like the dotted formulas either and prefer to write individual resonance structures. The latest on the hydrogen bond in acetylacetone is that it seems to be symmetric, [8] but I don't know how conclusive the interpretation is. (talk) 14:54, 31 May 2017 (UTC)
The diagram does not look to me like a π bond to H, since it's not contiguous with the curve curve of delocalized π that runs O–C–C–C–O. But this diagram is in keeping with that ref, which is also cited in the Acetylacetone article. DMacks (talk) 04:09, 1 June 2017 (UTC)

Jamal Lasri[edit]

I have issues with Lasri condensation which I suspect may eventually require an admin - I don't really have enough evidence to start anything yet and I don't want to get in trouble because of that, so I'm just going to explain things here in the hopes of getting some advice. The Lasri condensation is named in honour of Jamal Lasri, which is impressive as the paper detailing the reaction only came out this year (there's no DOI and I cannot find it at all online), so there's obvious issues of WP:UNDUE there. That makes me suspicious of the people editing the page (new editors who aren't editing anything else). However while digging I also found Draft:Jamal Lasri which seems to have become marooned because of Wikipedia:Sockpuppet investigations/Jamal.lasri/Archive which kind of implies that there's someone more serious going on here. --Project Osprey (talk) 21:27, 1 June 2017 (UTC)

I CSD#G5ed the draft and blocked the editor who has written it as part of that sock-drawer. DMacks (talk) 05:22, 2 June 2017 (UTC)
Many thanks, I tried PRODing Lasri condensation but was overturned by the page editors (unsurprisingly). I'm not sure it meets the criteria for a speedy deletion so I'm to take it to AfD unless you have any objections? --Project Osprey (talk) 08:09, 2 June 2017 (UTC)
No objections. That will help bring extra eyes, especially since it involves long-term site abuse. DMacks (talk) 12:12, 2 June 2017 (UTC)

I have added some of the material from the Lasri condensation page to other articles, and on further checking realised that the well-known formation of 3,5-diphenyl-1H-pyrazole involves the reaction of chalcone with hydrazine hydrate, either in the presence of sulfur (2008 ref: doi:10.1002/jhet.5570450231) or sodium persulfate (2014 ref: doi:10.3987/COM-13-12867). What seems to be being claimed as the "Lasri condensation" involves using a hydrazone instead of the hydrazine + sulfur oxidant. I can find no references to a Lasri condensation nor web-links that don't track back to WP. My motivation in adding content to pyrazole, chalcone, azine, and hydrazone was so that the non-notable Lasri condensation page could be AfD'd with a rationale that relevant content is already in appropriate / potential articles and the claim of a named reaction is unsupported by sources and non-notable. I realise that my additions may be removed / trimmed as undue, which is fine.

I note particularly that DMacks has reverted me at chalcone and then added a comment on the generalisability of the approach to 3,5-disubstituted 1H-pyrazoles, which is undoubtedly true. The problem I have with the revert is it leaves two references neither of which refers to a hydrazone supporting a scheme using a hydrazone, but the only reference available is an "in press" article, which I admit is problematic. I am going to reinstate my edit to make the text accurate, but also seek input here on what we should do:

  1. Should we rename File:Scheme1jpg.jpg and File:Scheme1jpg.jpg from the Lasri article to something more appropriate? (I have used the first several times, but not the second).
  2. Alternatively, should we re-draw File:Scheme1jpg.jpg to use hydrazine hydrate and then ditch all mention of the in press article?
  3. Is there anything from the mechanistic description in the Lasri article worth using elsewhere? It includes reference to doi:10.1016/j.molstruc.2016.05.044 with the structure of the azine from fluorenone, FYI.
  4. Should we go ahead and AfD the Lasri condensation article?
  5. Is Lasri notable? I see that Jamal Lasri is salted after apparently five deletions (most recently in 2015) though there is an es:Jamal Lasri article, which provides links to ar:Jamal Lasri, it:Jamal Lasri, sh:Jamal Lasri, and az:Camal Lasri.

All input / thoughts welcome.  :) EdChem (talk) 08:27, 12 June 2017 (UTC)

Take it to AfD first, if its gets deleted then the images will likely need to be deleted too. I don't think he meets WP:PROF. I had meant to do this myself but real-life has caught up with me so I'm not editing much at the moment. --Project Osprey (talk) 10:07, 12 June 2017 (UTC)

Transporter Classification Database[edit]

The Transporter Classification Database is an important source for information about transporter proteins, and it is labeled as CC-BY. But in fact this database often copies content from copyrighted journal articles (likely in good faith, because the people who wrote the database entries also wrote the copyrighted journal articles--but a problem nonetheless). Just wanted to get the word out so that we don't accidentally import copyright violations from this source. See Wikipedia:Contributor copyright investigations/Transporter Guy for more information. Calliopejen1 (talk) 21:01, 6 June 2017 (UTC)

Constituent of tobacco smoke[edit]

I recommend that we remove notes in chemical articles of the following type: "Carbon disulphide is a constituent of tobacco smoke.<ref name="TalhoutSchulz2011">{{cite journal|last1=Talhout|first1=Reinskje|last2=Schulz|first2=Thomas|last3=Florek|first3=Ewa|last4=Van Benthem|first4=Jan|last5=Wester|first5=Piet|last6=Opperhuizen|first6=Antoon|title=Hazardous Compounds in Tobacco Smoke|journal=International Journal of Environmental Research and Public Health|volume=8|issue=12|year=2011|pages=613–628|issn=1660-4601|doi=10.3390/ijerph8020613|pmid=21556207|pmc=3084482}}</ref>". No doubt that these additions are well intentioned, but that is sufficient criterion for inclusion.

My argument: One could list thousands of things that contain H2S (and other common chemicals), but we are not a in the listing business. The same editor User:Bosley John Bosley also adds the category of Category:Constituents of tobacco smoke, which would appear to achieve the same goal.--Smokefoot (talk) 13:10, 11 June 2017 (UTC)

H2S and Carbon disulphide have significant Health effects - which are we talking about? Bosley John Bosley (talk) 15:34, 11 June 2017 (UTC)
I agree with you in this instance. I was thinking the category was unsuitable. The constituents can be listed in the tobacco smoke article, and only highly significant substances need to mention tobacco (eg nicotine, tar, carbon monoxide). Another unsuitable category: Category:chloride, when we have Category:chlorides. Graeme Bartlett (talk) 13:16, 11 June 2017 (UTC)
Smokefoot above states that we are not in the listing business - how can you both agree with him and state that the constituents can be listed in the tobacco smoke article? I started the category because the list was simply too unwieldy. If there is an issue with [[category:Constituents of tobacco smoke]] then this should be raised at WP:CFD - unlike Category:chlorides the subject matter has a wider circle of stakeholders than wikipedians from WikiProject Chemistry - is tar even a chemical? Bosley John Bosley (talk) 15:34, 11 June 2017 (UTC)
I agree as well, one could continue this till the absurd .. 'water is a constituent of sea water, tap water and rain water'; 'CO2 is a constituent of air, tobacco smoke, car exhaust gasses' .. The constituents can be listed in the article of the mixture, not on the articles of the individual constituents. --Dirk Beetstra T C 13:20, 11 June 2017 (UTC)
A preschool kid knows that sea water, tap water and rain water contains water. I doubt even an oncologist could list at least 73 known carcinogens in cigarette smoke <ref>[[Lung Cancer]]</ref> Absolutely every category in Wikipedia could instead have been be listed in an article...However, some bright spark came up with the idea of categorisation. Bosley John Bosley (talk) 15:34, 11 June 2017 (UTC)
@Bosley John Bosley: Categorisation is one thing, but adding this on each article is IMHO too much. And also for the categorisation, it is impossible to do that consistently. Again, water is a constituent of a lot of things, so the ad absurdum reduction of the argument for carbon disulfide would result in many categories on some compounds. And you can do that already for stuff like carbon disulfide - I am sure that you can find it in crude oil, and, knowing its properties, probably even still in the petrol you put in your car). That then goes to the next ad absurdum reduction - many chemical compounds can be found as trace compounds in many places (giving arguments to homeopathy to put categorise them there?). I can't fathom the amount of problems this gives. I think that this should be done with due care. --Dirk Beetstra T C 08:25, 12 June 2017 (UTC)
I also agree.JSR (talk) 14:48, 11 June 2017 (UTC)
I also disagree with you Bosley John Bosley (talk) 15:34, 11 June 2017 (UTC)
John Bosley, I am convinced that you are acting with good intentions, even if it appears that consensus is against adding your commentary to so many articles (sort of a spamming exercise, which is usually a bad thing here). My guess is that you are underestimating two things that the other commenting editors are more experienced with: (i) the chemical complexity of our world and (ii) the commitment of editors to keep articles from turning into lists of factoids. Maintaining a disciplined article is a constant battle because the entire physical universe is a jumble of chemicals, and many some editors are intent to remind readers of the stuff used to kill ants, fuel model airplanes, or found as a component of something. --Smokefoot (talk) 16:19, 11 June 2017 (UTC)
Spamming is an issue for WP:ANI. I believe the commitment of editors more experienced with the chemical complexity of our world might be more productively demonstrated with the help on the list below. Factoids are trivial or unreliable information that is reported and repeated so often that it becomes accepted as fact. That is not the case here. Bosley John Bosley (talk)
We also have Tobacco-specific nitrosamines about a certain subcategory of these chemicals. DMacks (talk) 21:20, 11 June 2017 (UTC)

On a related note, Tobacco smoke already has a list of tumorigenic agents (which it tries to organise by class - an idea I like). This list is longer than the one at List of cigarette smoke carcinogens, so there's an obvious question about merging that fork back in, however the sourcing of the list in unclear with no obvious references. --Project Osprey (talk) 10:46, 12 June 2017 (UTC)

Synonym Check[edit]

While we are on the subject (above) are there any super dooper chemists who could doublecheck whether an synonymous article does infact exist for any of the chemicals (contained within tobacco smoke) below?

Bosley John Bosley (talk) 16:05, 11 June 2017 (UTC)

n-Propylbenzene does not but it has several mentions in other articles and should probably be created to resolve its redlink on Propylbenzene. DMacks (talk) 20:42, 11 June 2017 (UTC)
Stubbed. Please contribute (de.wp and others have an article with some sourced content already). DMacks (talk) 04:13, 12 June 2017 (UTC)
I added CAS#s to the above list. It's a pretty good way to search for articles on WP, and likewise key info to include in an article and for pubmed and other lit searches. I couldn't find * 2-Amino-3-methylimidazo(4,5-b)quinolone in pubmed, but I did find 2-Amino-3-methylimidazo(4,5-f)quinoline (CAS# 76180-96-6) that lists "IQ" as a synonym. DMacks (talk) 21:38, 11 June 2017 (UTC)
Structural searching doesn't find any matches either. On the face of it I would have though that the nitroso compounds (which are all based on simple compounds that we already have pages on) would make valid pages of their own. I'm not so sure about the others, they're all fairly niche poly-aromatics, I doubt we'd even be able to find boiling points for them. --Project Osprey (talk) 10:38, 12 June 2017 (UTC)
Thanks guys, I suspect (subject to my near zero competence) that some such as N-nitrosodiethanolamine maybe the tobacco-specific chemicals found only in tobacco products mentioned above. If (and only if) I find WP:RS refs I plan to create/merge them into that article (estimated timescale = months). If this is not a good idea ...speak now...Bosley John Bosley (talk) 13:53, 13 June 2017 (UTC)
I'd be glad to help on the chemistry if you develop an article that describes (even lists) these components. The aspect that I was objecting to was the mention of tobacco-relatedness in the individual chemical articles for reasons stated above. BTW, those entries will eventually be removed in view of the consensus above, again time scale of days or weeks.--Smokefoot (talk) 14:07, 13 June 2017 (UTC)

Draft:Generation of Carbocationic Synthons[edit]

Will someone please review Draft:Generation of Carbocationic Synthons? Please be aware that the author never responds to anyone. She just submits stuff. If it is a useful topic but needs work, someone else has to do the work. She just throws things over the transom. I can see that it would benefit from the addition of links to related topics to facilitate understanding and assessment. Is it worth working on? Robert McClenon (talk) 00:28, 14 June 2017 (UTC)

I have knocked it back as Carbocationic synthon already exists. Graeme Bartlett (talk) 11:08, 14 June 2017 (UTC)
That article does not define "Carbocationic synthon" that I could find. Nor could I find a citation to a secondary source with "Carbocationic synthon" in the title. Oh well, its only Wikipedia. --Smokefoot (talk) 13:12, 14 June 2017 (UTC)
There is not even a primary source that has that in the title, only a passing mention. So its is certainly not notable. I have changed to a redirect to Synthon. Graeme Bartlett (talk) 01:39, 15 June 2017 (UTC)
Thank you. This is a very strange editor who submits reasonably good technical stuff to AFC but never pays any attention to the responses. Sometimes her submissions are accepted, and she resubmits them a month or two months later anyway, and they have to be declined as already existing. We assume that there is a human behind the user name, but they don't pass the Turing test, because they don't either seem to be trying to act like a human or trying to act like a bot. Robert McClenon (talk) 22:38, 15 June 2017 (UTC)

Facto Post – Issue 1 – 14 June 2017[edit]

Facto Post – Issue 1 – 14 June 2017
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This newsletter starts with the motto "common endeavour for 21st century content". To unpack that slogan somewhat, we are particularly interested in the new, post-Wikidata collection of techniques that are flourishing under the Wikimedia collaborative umbrella. To linked data, SPARQL queries and WikiCite, add gamified participation, text mining and new holding areas, with bots, tech and humans working harmoniously.

Scientists, librarians and Wikimedians are coming together and providing a more unified view of an emerging area. Further integration of both its community and its technical aspects can be anticipated.

While Wikipedia will remain the discursive heart of Wikimedia, data-rich and semantic content will support it. We'll aim to be both broad and selective in our coverage. This publication Facto Post (the very opposite of retroactive) and call to action are brought to you monthly by ContentMine.

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MediaWiki message delivery (talk) 09:33, 14 June 2017 (UTC)

Category:Alkenes and other categories with both a broad and a narrow definition.[edit]

For example the category Alkenes contains compounds that are not hydrocarbons, which is fine under a more broad definition of alkenes, but isn't under a narrower one. Since much of my editing consists of categorization of articles about chemical compounds, I would like to see if a consensus can be reached concerning what belongs in these types of categories. OrganoMetallurgy (talk) 01:11, 23 June 2017 (UTC)

I think that what is in this category should be the same as that the alkene article says it is, so it should only include compounds with only carbon and hydrogen. We need an unsaturated compounds category for the more generic situation: perhaps Category:C=C (which is too cryptic) or category:compounds with a carbon to carbon double bond -- (which is a bit verbose). Compounds only with C=N or C=O would not be classified as alkenes at all. You can see that I used category:unsaturated compounds for Trans-4,5-Epoxy-(E)-2-decenal, but that is perhaps too generic. Graeme Bartlett (talk) 08:41, 24 June 2017 (UTC)
As a non chemist, could I say I don't think Category:C=C is too cryptic (subject to a short description on the category page). Unfortunately there is an element of genius in the idea which will inevitably lead to strong opposition from the dull minded. Bosley John Bosley (talk) 10:08, 24 June 2017 (UTC)
I was thinking of creating either Category:Alkene derivatives or Category:Alkenes (hydrocarbon). OrganoMetallurgy (talk) 12:48, 24 June 2017 (UTC)
I quite like Category:Alkene derivatives, (it is clear and not too long) then we can have lower levels of Category:unsaturated fatty acids, Category:Enols, Category:Alkenones, Category:unsaturated dicarboxylic acids. etc Graeme Bartlett (talk) 07:28, 25 June 2017 (UTC)

Deep Carbon Observatory wants to sponsor a Wikipedia Visiting Scholar[edit]

Of possible interest to WikiProject members:

The Deep Carbon Observatory (DCO) is looking to sponsor a Wikipedia Visiting Scholar.

DCO is an initiative involving about 1000 chemists, physicists, geologists, and biologists collaborating to study various aspects of carbon deep within Earth. The project's Engagement Team, which is based at the University of Rhode Island (URI), would like to facilitate improving Wikipedia's coverage of topics related to deep carbon by providing an experienced Wikipedian with access to 9000 deep carbon-related publications as well as full remote access to the URI library's online resources (databases, ebooks, etc.). If convenient for the Visiting Scholar, they would also like to bring him or her to URI for a visit (expenses paid).

The Visiting Scholars program connects Wikipedians with educational institutions based on shared interest in a topic. Any editor in good standing is welcome to apply. Professional experience is not a requirement. For more information, see the Deep Carbon Observatory Visiting Scholars page. If you have questions, you can ping me here or leave a message on my talk page. --Ryan (Wiki Ed) (talk) 18:49, 24 June 2017 (UTC)