# Wikipedia talk:WikiProject Chemistry

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.

## Substrates and products merge

Just a quick post to both WP:MCB and WP:Chem. There are duplicate stub pages for substrate and product. Since in each case one copy just repeats the other I propose that they're merged into substrate_(chemistry) and product_(chemistry) with the biochem-specific parts just as a section.

Discussion on WP:MCB page. T.Shafee(Evo﹠Evo)talk 09:34, 20 January 2015 (UTC)

For reference, I've performed the merge and expanded the articles a bit. The input of any chemists would be very welcome! T.Shafee(Evo﹠Evo)talk 03:52, 10 February 2015 (UTC)

## Carl Djerassi

Carl Djerassi died over the weekend. He was a big contributor to early steroid chemistry but is probably best known for helping to develop the oral contraceptive pill. His article is in pretty good shape but if anyone can think of anything that's missing now would be a good time to add it as the page is currently getting several thousand hits per day. --Project Osprey (talk) 21:26, 2 February 2015 (UTC)

## Nomenclature Problem

Hello, I am aGastya. I am confused that American spellings for chemical compounds to be used or IUPAC ones? Like Sulfate vs Sulphate? aGastya 04:01, 7 February 2015 (UTC) — Preceding unsigned comment added by AgastyaC (talkcontribs)

See WP:SULF. DMacks (talk) 04:52, 7 February 2015 (UTC)

## Possibly notable chemist who died in last week's train wreck

One of the victims of last week's Valhalla train crash was Robert M. Dirks, a computational chemist with a doctorate from Caltech, where he also did a postdoc, who worked at D.E. Shaw Research in Manhattan. Since another victim, Walter Liedtke, has turned out to be notable, I decided to look into Dirks ... who seems to have coauthored quite a few papers, and his employer describes him as having made "tremendous contributions" to "the development of novel computational chemistry methods."

I've compiled what I've found on the article's talk page. I'd like some input from editors at this project who could say what's significant about his research, if it is significant, within the context of the notability criteria for academics and scientists than I am, and perhaps better qualified to judge if Dirks' research makes him notable. Daniel Case (talk) 16:41, 8 February 2015 (UTC)

Probably not. If he were notable, his name would/will come up without prompting. PhD's are virtually required to publish papers in chemistry, so that is a low bar. CalTech cranks out about 25 PhDs each year in chemistry. He went from his PhD to an investment bank, a career path that would indicate that he was going to develop is quantitative skills, not scholarship. Tragic nonetheless.--Smokefoot (talk) 16:58, 8 February 2015 (UTC)
Just noticed this, belatedly. Note that D. E. Shaw Research and D. E. Shaw & Co. are not the same thing; Dirks was an employee of the research group, not the hedge fund, and is an author on several of the company's papers. Nevertheless, I don't think he's notable in the Wikipedia sense. We don't have articles on any of the other company scientists as far as I can tell. Opabinia regalis (talk) 20:04, 21 February 2015 (UTC)
I work in the same field as him (DNA nanotechnology) and I can say that his publications are immensely impactful within this field. He developed the thermodynamic analysis algorithms that underlie NUPACK, a nucleic acid design suite that is the primary tool of this kind used in the field. I was thinking of making an article about him myself, I just need to dig up some third-party sources that aren't obituaries. I'm happy to work on it with you, Daniel Case, if you're still interested. Antony–22 (talkcontribs) 01:14, 22 February 2015 (UTC)
Fair enough, I was looking at the simulation side of things. Biographies of the marginally notable and recently deceased worry me a little - they're unlikely to be actively watched in the long term - but no objections. Opabinia regalis (talk) 05:26, 22 February 2015 (UTC)

## Carbohydrates

I draw attention to the deplorable state of many articles on carbohydrates. Just 3 examples from many

• pentose does not have either Fischer projections or cyclic structures
• hexose does have Fischer projections, but shows cyclic structure only for glucose and mannose
• Ribose has all the structures but none for deoxy ribose.

It's not just the content of these and other articles. The subject carbohydrate is not a good overview as it is limited to monosaccharides and disaccharides. Might I suggest that this subject area needs to be re-organized and that a lot of re-writing is also needed. Petergans (talk) 06:20, 10 February 2015 (UTC)

## Nomination for deletion of Template:InChI

Template:InChI has been nominated for deletion. You are invited to comment on the discussion at the template's entry on the Templates for discussion page. -- 70.51.200.101 (talk) 05:57, 11 February 2015 (UTC)

## Wikipedia session at ACS Boston meeting in August

The ACS Chemical Information division (CINF) is holding a technical session at the Fall ACS meeting in Boston, titled "Wikipedia and Chemistry: Collaborations in Science and Education". We're trying to highlight the contribution of Wikipedia to chemistry and to chemical education. If you have a suitable topic you'd like to present on, and you'd like to submit an abstract, submission is open until March 29th. If you have questions, by all means contact me on my talk page. Walkerma (talk) 04:23, 16 February 2015 (UTC)

This is just a quick followup to remind people - abstracts are due by this coming Sunday. I see I didn't post the full description before, which is:

Chemistry information on Wikipedia has an enormous reach and impact. In this symposium, the connections between Wikipedia editors and the wider chemistry community will be explored. In particular, collaborations between educators, students and regular editors (Wikipedians) will be examined to understand how Wikipedia editing can be set up as a successful class project. Educators will demonstrate how Wikipedia projects can help students with understanding subject matters and improving information literacy skills. Meanwhile, we will explore how educators and the Wikipedia community can work together through the Wikipedia Education Program to ensure students' contributions to Wikipedia are valid and effective. Finally, we will exchange ideas on how to involve more chemists in contributing to Wikipedia, and how to use the site wisely.

We are also organising an Edit-a-thon, so even if you're not presenting, we'd love for you to help with that. Thanks, Walkerma (talk) 20:25, 27 March 2015 (UTC)

## Wikipedia talk:Chemical infobox#Ordering Identifiers

More opinions on the order of the identifiers in the chembox would be appreciated. --Leyo 22:02, 17 February 2015 (UTC)

## IUPAC again

I've repeatedly heard from members of this WikiProject that articles should not be forced to blindly adopt IUPAC definitions or terminology in instances where they directly contradict common use by actual scholars, researchers, etc in a particular field. And yet, it appears that we have an entire policy page mandating strict adherence to IUPAC guidelines in articles: Wikipedia:Naming conventions (chemistry). How does that work? (+)H3N-Protein\Chemist-CO2(-) 14:43, 19 February 2015 (UTC)

See the 'exceptions' section. --Project Osprey (talk) 14:54, 19 February 2015 (UTC)
The IUPAC guideline is specific that it applies to chemistry articles. Now within that narrowed field, do we really have articles where this is contentious? Chemists in the UK aren't going to stop spelling it "sulphur" until the current generation dies off. However they're not likely to oppose IUPAC for sake of "common use" either. Andy Dingley (talk) 15:00, 19 February 2015 (UTC)

## LD50 vs LC50

Hi everyone, I had a question about LC50 values for several different gases. Is it okay to put an LC50 in the LD50 parameter, or is this something that should be put in the body of an article? As an example, I have a data sheet for chlorine trifluoride here that lists LC50 values in various organisms with exposure times, so I wanted to ask here about what to do since it's interesting/useful information. Thanks! Best, Emily Temple-Wood (NIOSH) (talk) 01:06, 21 February 2015 (UTC)

Are they measurements of subtly different things, or different terminology for essentially the same thing? (The discussion in the article LD50 isn't entirely clear to me.) If there's a subtle difference, perhaps there can be separate fields in the infobox for LD50 and LC50. Antony–22 (talkcontribs) 03:21, 21 February 2015 (UTC)
LC50 is the lethal concentration (of a gas) while LD50 is the lethal dose, usually given IV or orally. Emily Temple-Wood (NIOSH) (talk) 06:03, 21 February 2015 (UTC)
They are clearly different things. LC50 is a concentration and LD50 is a quantity, usually expressed as a mass. The difference lies in the fact that LD50 refers to a quantity ingested whereas LC50 refers to a concentration external to the organism. That's why exposure times are important in relation to LC50. Petergans (talk) 11:42, 21 February 2015 (UTC)
Okay, that makes sense. So my next question is, it is possible for a single substance to have both an LD50 and an LC50, or is only one or the other meaningful for each substance? In any case, they both sound equally important, so my instinct is that either or both should be listed in Template:Chembox. Antony–22 (talkcontribs) 18:43, 21 February 2015 (UTC)
(added after the comments below) Consider, for instance, chlorine gas. LC50 (LC=Lethal Concentration) gives the concentration at which exposure to the gas will be, eventually, lethal in 50% of cases. LD50 (LD=Lethal Dose) gives the amount of gas that, when inhaled, will be lethal in 50% of cases. For gases there is no ambiguity. For liquids LD50 refers to ingestion, but LC50 is not so well defined; it could apply to topical exposure, or, in the case of a volatile liquid, exposure to the evaporate. For solids LC50 has no real meaning. Petergans (talk) 05:15, 22 February 2015 (UTC)
I would guess that in principle you could have both. But it's difficult to administer a weighed amount of a gas. So it makes most sense to use LC50 for gasses and LD50 for solids and liquids. Maproom (talk) 19:17, 21 February 2015 (UTC)
LC50 can be used for liquids or solids dissolved in a medium, particularly in in vitro testing such as the concentration of an antibiotic that will kill a bacteria. — Preceding unsigned comment added by 173.62.240.135 (talk) 19:57, 21 February 2015 (UTC)

So, returning to this - should we have a separate parameter in the chembox for LC50 or just add it to LD50 and note that it's an LC50? Thoughts? I don't particularly have a preference. Emily Temple-Wood (NIOSH) (talk) 22:30, 26 February 2015 (UTC)

There was the same issue in de.wikipedia, too. The consensus then was, to replace the LD50 parameter in the chembox by a more general one and to use de:Template:ToxDaten. Like this, the input is more flexible (see de:Benzaldehyd for an example [bottom of the box] with both LD50 and LC50 values). I don't say that a similar solution would suit best also on en.wikipedia. --Leyo 14:51, 27 February 2015 (UTC)
@Leyo: That looks useful, though I don't speak enough German to follow well. DePiep, as the Chembox guru, would this be an easy thing to fix/do if we get a consensus for it? Best, Emily Temple-Wood (NIOSH) (talk) 03:20, 5 March 2015 (UTC)
Of course we'll implement the outcome of a good talk. -DePiep (talk) 07:06, 5 March 2015 (UTC)
My notes. About the German wiki, Leyo points to. It knows these types of toxy measurements: LD50, LC50, LDLo, LCLo, LCt50, TDLo, TCLo, EC50, IC50, LD, LC. This name is mentioned, but in the rh side with the data. It also can add the organisme, intake etc (required parameter!). Then they produce a righthand text like (See de:LSD):
• Toxikologische Daten: 11,7 mg·kg−1 (LD50, Ratte, oral, Hydrochlorid)[1].
We too could add this, under one label. I don't know if we must make all those fields required input. Also, it is a laboratoy-result, ie more meaningless for The Reader (?, I ask). However, this is a bigger excercise to develop (all this input is done through a single template). And this solution can be used in many more Chembox inputs (The dewiki has all input this way).
For now: Since LC50 is well defined, we could start with adding it old style, enwiki style: in a separate datarow. Our article on LD50/LC50 could be improved anyway. Also I'd like to hear from medicine editors on how & what to present. Later I'll have time to make proposals here. -DePiep (talk) 07:06, 5 March 2015 (UTC)
• I add, replying to earlier posts here (the top half, eg Petergans): we can simply add a data row LC50, and leave it to the article editor to make a useful entry. Thew template does not chekc the sens of its data. As wiki works, the nonsense-input (like: an LC50 value for a solid) will probably be edited out in the end. -DePiep (talk) 07:14, 5 March 2015 (UTC)
• I add #2: can someone explain why this LD50 is not in sister template {{Drugbox}}? (in the long term, these two can merge IMO). -DePiep (talk) 07:22, 5 March 2015 (UTC)
@DePiep: Yay, thank you so much! Emily Temple-Wood (NIOSH) (talk) 16:24, 14 April 2015 (UTC)

## Anyone heard of "Groove's process"?

Yesterday I started this AfD for the articles groove synthesis and groove halogenization, which are clunky descriptions of the synthesis of haloalkanes from alcohols. I couldn't come up with any connection between these names and the reaction, but I did find a handful of references to "Groove's process" as a term for it. It does seem to be something students are searching for, but I can't find anything to substantiate the name. Anyone heard of this? Opabinia regalis (talk) 05:33, 22 February 2015 (UTC)

In general a very simple transformation which is also a named reaction tends to be a very old named reaction - and some of those names just fall out of use. The Menshutkin reaction is now generally just called quaterisation, no one really calls the Darzens halogenation anything anymore. In this case I would have thought that Lucas' reagent would have covered everything we need. --Project Osprey (talk) 09:50, 22 February 2015 (UTC)
Thanks - yeah, I know these are often just obsolete names, but Darzens halogenation et al. are names that can be found in typical English-language organic chemistry references even if they're not really used anymore. "Groove's process" doesn't appear in equivalent places, but does seem to be search term (used mostly by Indian students, it looks like). I wondered if anyone outside of homework-help sites had actually run across that usage that would warrant a redirect. Opabinia regalis (talk) 21:26, 22 February 2015 (UTC)
Well I'm in work tomorrow and my access to literature will be much better, so I'll do a little digging and post again if I find anything. --Project Osprey (talk) 21:39, 22 February 2015 (UTC)
There is absolutely nothing in the normal scientific literature. The best I could find were two references to it in text books "The Pearson Guide To Organic Chemistry For The Iit Jee" and "Together With Iit-Jee Chemistry", LIT JEE being a university entrance exam in India. I can only look at one of those via Google Books (The Pearson Guide) and it's a bit weird. There are spelling errors ("MarkownoKoff's rule" instead of Markovnikov's rule) and strange re-inventing's of chemistry (The obscure Rydon Reagents are now the Rydone process: first equation below is what the book said happens, the second is what should actually be shown)
R-CH2OH + Br2 + (C6H5O)3PO → R-CH2Br + C6H5OH + (C6H5O)2POBr
(C6H5O)3P + MeI → (C6H5O)3P+Me I-
(C6H5O)3P+Me I- + ROH → (C6H5O)2P+(Me)OR I- + C6H5OH → (C6H5O)2P(O)Me + RI
Most of the information in the book looks accurate but there's enough strange content to stop me from trusting it. By extension I don't think that the "Groove's process" really exists (at least in terms of it being named after a Dr Groove), I think we can safely delete those pages or at least tern them into redirects. --Project Osprey (talk) 18:08, 23 February 2015 (UTC)
Thanks, glad I'm not the only one who thinks this is strange! I think the only title with any basis for a redirect would be Groove's process, since the other variants turn up basically nothing. But the existence of a redirect sort of implicitly acknowledges the existence of the name - it's harmless enough but in general neologisms like this whose only source is clearly unreliable don't survive here. Opabinia regalis (talk) 05:27, 24 February 2015 (UTC)

## "Binary liquid" notability

Is "binary liquid" an actual notable term, that doesn't just mean "two liquids mixed together"? The only source I can find that refers to it as something distinct is the Wikipedia page. Jay Vogler (talk) 21:27, 1 March 2015 (UTC)

I see that the first and third external links of binary liquid lead to the same article, which does not contain the word "binary" and is about foam; while the second gives a "not found" error. It looks to me like a poorly constructed hoax article. Maproom (talk) 08:13, 2 March 2015 (UTC)
In Google Scholar searching for "binary liquid" nets 38,100 hits; the general concept seems notable enough. Binary liquid as "two inert liquids, that when mixed together, do something interesting" seems much less so, but binary liquid explosives have been discussed as possible/improbable terrorist devices, e.g., flying toilet terror labs. --Mark viking (talk) 11:59, 2 March 2015 (UTC)
All those mentions seem to be "binary" modifying some type of liquid composition, to note that it's two parts; nowhere do I see "binary liquid" on its own as a notable thing. In the case of a binary liquid explosive it's not the term binary liquid which is of interest, but a liquid explosive which happens to be binary, and I'd argue information on that fits much better into binary explosive, maybe binary liquid explosive. This looks a lot like someone made up their own specialized definition and tossed it into Wikipedia for kicks. Jay Vogler (talk) 14:19, 4 March 2015 (UTC)
Actually, I take part of it back, study of the properties of binary liquid mixtures seems to be a thing. It still has nothing to do with the definition as currently written, though, and I'm not sure whether it deserves its own page any more than binary amalgam or binary gas, etcetera, do. What could be said about the idea beyond a dictionary definition? Jay Vogler (talk) 14:20, 4 March 2015 (UTC)

## N-Acylamides

I could use some input about the relatively new article N-Acylamides. The article is basically about fatty acid amides and I think it should be merged into that article. But the article content has some problems I would like to address before I merge it. First of all, the writer seems to be unclear about the difference between an amine and an amide (which leads to the bad nomenclature in the title, to begin with). I'm not sure I trust content written by someone without enough knowledge of the topic to understand the distinction between those two functional groups. Setting aside the nomenclature problems, does the rest of the content hold up to scrutiny? ChemNerd (talk) 20:10, 3 March 2015 (UTC)

Looks very suspect. --Smokefoot (talk) 23:08, 3 March 2015 (UTC)
Looks like a confused student effort? The description is bad and the glycerols don't belong, but the term "N-acyl amide" does get used in the literature sometimes to refer to a fatty acid attached to an amino acid or ethanolamine. I think it's part of the general terminological muddle on what to call N-acylethanolamines. Most of these are endogenous cannabinoids involved in lipid signaling. Opabinia regalis (talk) 05:03, 4 March 2015 (UTC)
Some of the entries in the article's table are n-acylamino acids (e.g., N-acyl glycine) which are structurally distinct from fatty acid amides. They should be split out into a new article or deleted. Boghog (talk) 05:39, 4 March 2015 (UTC)

## The Merck Index: updating citations

My Royal Society of Chemistry colleagues and I propose to update citations to The Merck Index. As there may be CoI concerns, please review the proposal, and comment, at Wikipedia:GLAM/Royal Society of Chemistry/Merck. Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 15:50, 4 March 2015 (UTC)

## FAR

I have nominated Aldol reaction for a featured article review here. Please join the discussion on whether this article meets featured article criteria. Articles are typically reviewed for two weeks. If substantial concerns are not addressed during the review period, the article will be moved to the Featured Article Removal Candidates list for a further period, where editors may declare "Keep" or "Delist" the article's featured status. The instructions for the review process are here.--Jarodalien (talk) 14:52, 7 March 2015 (UTC)

## I would ask general attention

…from members of Wikiproject Chemistry at the Oxygen article, which was listed as FA, but has had some issues arise.

I am a newcomer there, arriving to edit because I wanted to reference the information on the structure of this homonuclear diatomic, and found the article in need of attention for its molecular orbital description, and successfully edited that.

I have, however, run afoul of two European, non-native English speaking editors for proposed changes that challenge their view of info box image content. There is no need to repeat those arguments here, for they are not the main issue any more.

The main issues are now three:

• My edits are now being reverted just because they are mine. Because there are two editors involved, they view themselves as a consensus, and feel justified in their ability to do this.
• Their reversions are comprehensive, throwing out baby with bath water. In the last reversion, I had (1) combined physical properties prose in two locations into one, separating it from molecular structure (MO) prose, and moving the phys prop text up in the article, (2) corrected gross errors in prose regarding an introduced image of a discharge tube, and (3) touched up the prose in the MO diagram section I had added earlier. All of these were reverted en masse with a personally directed edit summary.
• Their reversions protect the very bad edits of one of the editors, which lack chemical expertise and do not pass as acceptable English.

On this last matter, I will give an example, and leave it for parties interested in high quality article evolution and protection to have a look.

Here is a recent edit made by one of the editors:

In an oxygen gas discharge spectrum tube, the molecular orbitals of oxygen are stimulated to emit light. The operating conditions for the oxygen image discharge tue: are a pressure of 5-10 mbar, a high voltage of 1.8 kV, a current of 18 mA and a frequency of 35 kHz. During the recombination of the ionized gas molecules, the characteristic color spectrum is emitted. In this case, a small part, caused reversibly formed by the supply of energy ozone. This kind of spectrum tubes are also important to study the spectral lines with a spectrometer.

Note that the text is rife with misspellings/English errors, and added very technical prose without any sources. I am a professional chemist, and could simply not begin to make sense of its meaning. Here is the correction I made that was reverted:

In an oxygen gas discharge spectrum tube,[clarification needed] the oxygen is stimulated to emit light.[citation needed] The operating conditions are a pressure of 5-10 mbar, a high voltage of 1.8 kV, a current of 18 mA and a frequency of 35 kHz.[original research?][citation needed] During the recombination of the ionized gas molecules,[clarification needed] a characteristic color spectrum is emitted.[citation needed] This kind of excitation is also important in general to the study of spectral lines with aid of a spectrometer.[clarification needed][citation needed]

In addition, this note was added, hidden in the article text, with the bracket-bang markup language:

• Content referring to molecular orbitals emitting light removed as fundamental error. THIS SENTENCE REMOVED AS GIBBERISH: "In this case, a small part, caused reversibly formed by the supply of energy ozone."

My correcting and tagging edit was made, not in any sense as text to remain in the article "as is", but as a starting point to move the original poor edit in a direction to make it acceptable. (Only the grossest of error, that MOs emit light, and the completely incomprehensible prose were removed.) My edit was reverted, so the original, error-filled prose again appears. [The error-filled edit was by the first of the editors, and is what I referred to in (2) above. My edit was reverted carte blanche with the further edits (1) and (3), by the second editor, who returned the error-filled prose to the article.]

Note, the two editors in question insisted that the discharge tube image was needed in this FA article, and I insisted that if it appeared, prose needed to appear to explain the image, and how it fit into the article. I have no issue with the appearance of the image, just with the editorial control and poor quality that derives from the work of these two editors.

Finally, note, that the personal reversion by the second editor recombines the physical properties and molecular structure sections, which I believe are better discussed separately, and returns the problematic discharge tube prose to a section largely about physical (ground state) properties.

I leave this entirely in the hands of the Project. I haven't time or desire to fight with self-interested editors controlling an article as if it is their own. Le Prof Leprof 7272 (talk) 13:50, 10 March 2015 (UTC)

My comments on the situation above, not that I am a mind reader or analyst: An edit like "In an oxygen gas discharge spectrum tube,{{what?}} the oxygen is stimulated to emit light.{{cn}} The operating conditions are a pressure of 5-10 mbar, a high voltage of 1.8 kV, a current of 18 mA and a frequency of 35 kHz.{{OR}}{{cn}} During the recombination of the ionized gas molecules,{{what?}} a characteristic color spectrum is emitted.{{cn}} This kind of excitation is also important in general to the study of spectral lines with aid of a [[spectrometer]].{{what?}}{{cn}}}}" could be seen as antagonistic. Coming from an editor with what could be seen as a pretentious user name "LeProf" probably makes such corrections seem stinging. If you find the prose so lacking, then I would recommend fixing it vs complaining about it. If an article is being over-protected by editors, then incremental (constructive) edits are required. If even incremental edits (not tagging) doesnt work, leave the alternative phrasing on the Talk page for some future edit-arguing/consensus forming process and move on to a more malleable article. Wikipedia has a ton or bio-organic articles that would really benefit from someone with your background. Those are my 2 cents. --Smokefoot (talk) 17:46, 10 March 2015 (UTC)
The conflict between established contributors without the real world "qulification" and the real world academic with no reputaion at Wikipedia is always ending in suffering. The article Oxygen became a featured article and this needed a lot of work of alot of people. I was part of two very bad experiences and one ended with a chemist leave wikipedia, a chemist with a name reaction associated to his name. Is there a need to rush this? Is the problem in the article making it necessary to do tha mass tagging. Start a discussion on the talk page and stay on the path with the necessary patience. I am willing to help. Here are enough good chemists and wikipedia editors with reputation which will help with the problem. Wikipedia is a slow system with its own rules which are very much different what I learned in the university life. --Stone (talk) 23:26, 10 March 2015 (UTC)
All comments above apt, , @Stone: but no one with real world demands in the chemical field has time for the nonsense of having carefully constructed, meaningful prose reverted by individuals who neither have training nor writing credentials to be doing anything of the sort. When I happened upon the Oxygen article article, the MO explanation was simply wrong, and so I found a good UK text (Jack Barrett's) whose correlation diagram matched one at Wikimedia Commons, then integrated the MO correlation diagram and explanatory text into the article. At the same time I noticed a picture of a discharge tube that appeared out of place, and with no supporting text information. I moved that orphan image to Talk, explained what was needed for its return, and that is when the firestorm started. The baseless reverting and editing that followed reinserted twice-appearing superficial information about physical properties, and mucked up the MO section—see current Oxygen#Properties_and_molecular_structure and the edit history. (You can see the MO digram now follows immediately after the statement "At standard temperature and pressure, oxygen is a colorless, odorless gas…" though there is an explicit Physical properties section further below.) At the same time, the discharge tube image—which appears because one of the editors runs a private, small museum that features these, and he believes his images belong in all articles possible— was returned to the article, with placement in the Oxygen#Physical_properties section [sic.]. Moreover, my editing of the description of the discharge tube was removed, carte blanche, and the illegible prior material was returned (see the Talk section, there). Bottom line, stilted, noun-verb disagreeing description of this misplaced image was returned in place of a good chemist's English, and remains to this day:

In an oxygen gas discharge spectrum tube, the molecular orbitals of oxygen are stimulated to emit light. The operating conditions for the oxygen image discharge tue: are a pressure of 5-10 mbar, a high voltage of 1.8 kV, a current of 18 mA and a frequency of 35 kHz. During the recombination of the ionized gas molecules, the characteristic color spectrum is emitted. In this case, a small part, caused reversibly formed by the supply of energy ozone. This kind of spectrum tubes are also important to study the spectral lines with a spectrometer. [Bold emphasis of mistakes added.]

Granted, to take the convoluted prose from what they originally entered to anything remotely readable required tags to call attention to the need for clarification (leading to an appearance viewed by as antagonistic). But can anyone here otherwise make full sense of this completely unsourced paragraph? If not deleting part and parcel, what is the option besides leaving what one can, and tagging the rest? Someone, anyone, look to see what has become of this acknowledged good article. It is for this Project, and inorganic and chem education individuals here, to deal with. I'll return from time to time, and prod, but I will waste no more time doing solid, content-professional edits that get reverted by hobbyists that insert unsourced, near illegible material. If it isn't important enough for the inorg and chem ed folks here, it cannot be important enough for me. Cheers, and thank you to all for your real contributions. Tres bien, et bonne nuit. Le Prof Leprof 7272 (talk) 07:17, 25 April 2015 (UTC)

## Indium tin oxide

Please could someone replace the bespoke infobox on Indium tin oxide with {{Chembox}}? Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 14:07, 12 March 2015 (UTC)

ITO is a solid solution of roughly 90% In2O3 and 10% SnO2 -composition is variable- and therefore physical poperties too. Mixtures like this and other "doped" inorganics don't fit with the chem box which is designed for chemical compounds. What do others think? Axiosaurus (talk) 14:42, 12 March 2015 (UTC)

Exactly. This sort of things has come up before. Thus far, the only exceptions which I'm aware of are the mineral acids, and kinetically unstable chemicals such as nitrogen dioxide which is in equilibrium with dinitrogen tetraoxide. Plasmic Physics (talk) 11:27, 14 March 2015 (UTC)
Would there be any profit in a dedicated infobox, or adding parameters to {chembox} for these? At least we'd have a what-links-here list. -DePiep (talk) 22:14, 18 March 2015 (UTC)
I'm not sure that I understand what you're asking. If it is whether I agree with the use of chemboxes for the mineral acids, then no, I see no way in which theses chemboxes enrich the articles or benefit the reader. To be sure, I'm not talking about the anhydrous, pure acids, but their solutions, c.f. Hydrogen chloride and Hydrochloric acid. Plasmic Physics (talk) 10:28, 20 March 2015 (UTC)
So, {Chembox} can not be used for these. OK.
My other question is, whether it would be useful to create a tempalte, say {Infobox chemical mixture}, that could cover these articles (substances). As it is now, Indium tin oxide has an in-the-article crafted infobox, like:
```{{Infobox
| label1 = ...
| data1 = ...
}}
```
So there are no dedicated or specific parameters available. If the answer is no, I'm :-) with that too. Must say, I have no clue for the answer because I'm not into chemistry, I'm more into templates. -DePiep (talk) 11:09, 20 March 2015 (UTC)
What would need to be created is an infobox that somehow demonstrates how the chemical properties of the mixture varies with composition, not just that it varies, which is necessarily true. I suspect that such an infobox which coveres a similar number of properties as the chemboxes would simply be too unwieldy to be practical, which is why I suggest that it should suffice to discuss in detail the variation of properties in the main article space, with only a few tables. Plasmic Physics (talk) 11:21, 20 March 2015 (UTC)
That would mostly merit parameters like `|compound1 =`, `|formula1=` (+ indexes 2, 3, ..). Then maybe a list of mixtures: `|mix12=40%, 60%` with meaningful properties `|mix12_mp=`, `|mix12_application=`. Just popping ideas. -DePiep (talk) 11:43, 20 March 2015 (UTC)
I add, a table and especially a graph would be more telling (horizontal axis having the mixture %). -DePiep (talk) 11:45, 20 March 2015 (UTC)
For alloys like solder. -DePiep (talk) 11:47, 20 March 2015 (UTC)
I didn't even consider mixtures with more than three components such as thermite (It often does). Plasmic Physics (talk) 20:02, 20 March 2015 (UTC)
Actually, I am asking like: is this worth a sandbox demo? Would you make development suggestions? I surely won't push it up your watchlist ;-) ! -DePiep (talk) 20:19, 20 March 2015 (UTC)
I suppose I could. Plasmic Physics (talk) 23:30, 21 March 2015 (UTC)

## MOS question

The chemistry MOS says the following about line equations:

Avoid the use of [itex] notation: the existing character set is adequate to enter reaction data

I found an article using $\rightleftharpoons$ (i.e., [itex]\rightleftharpoons[/itex]) and I tried to find a replacement among the character sets offered (above and below the edit box). Am I just looking in the wrong place for this? Or is that type of reaction diagram deprecated? Thank. Ian (Wiki Ed) (talk) 20:28, 18 March 2015 (UTC)

Try {{eqm}}. It works by inserting an image that is matched to the normal fontsize, so it's not truely "the existing character set", but it sure acts as if it were in many standard uses. DMacks (talk) 20:33, 18 March 2015 (UTC)
Thanks! Ian (Wiki Ed) (talk) 21:05, 18 March 2015 (UTC)
Any reason not to use the unicode ⇌ ? Christian75 (talk) 08:07, 19 March 2015 (UTC)
That's U+21CC rightwards harpoon over leftwards harpoon (HTML `&#8652;` · Arrows (Unicode block)). "eqm" is from "is in equilibrium with". -DePiep (talk) 13:30, 19 March 2015 (UTC)
and equlibrium is symbolized by two harpoons - so any reason not to use the unicode? Christian75 (talk) 17:59, 19 March 2015 (UTC)
I am supporting your point, Christian75. I was just adding a U+ reference. -DePiep (talk) 18:18, 19 March 2015 (UTC)
, . What about these then? Plasmic Physics (talk) 09:48, 20 March 2015 (UTC)
Nice! I think we avoid the use of math because you can't copy and paste it (in MS Word is renders as images) so to answer Christian, I think any Unicode character is acceptable. --Project Osprey (talk) 09:56, 20 March 2015 (UTC)
re Plasmic Physics: , are not available in Unicode. The mirrored one (wrt arrow direction) is: U+21CB leftwards harpoon over rightwards harpoon (HTML `&#8651;`).
Clearly, Unicode decided not to use its chemical meaning in the names ("equilibrum"), but a descriptive name instead. -DePiep (talk) 10:16, 20 March 2015 (UTC)
──────────────────────────────────────────────────────────────────────────────────────────────────── We are left with the option to replace, in {{eqm}}, current image with the Unicode character. The only objection I can think of is: when used in combination with , (images) in that same article, there might be a style break within a page? I don't know. -DePiep (talk) 20:10, 20 March 2015 (UTC)

## AfC candidates

Would anybody care to improve and publish:

? Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 17:41, 20 March 2015 (UTC)

I'm not that familiar with the draft-to-article process, but these need some 'peer' checks & edits I understand, then? (Sometimes I just start a bold stub and that stays silently ...) -DePiep (talk) 20:15, 20 March 2015 (UTC)
The second is not released for assessment. But are bot topics suitable for Wikipedia? Graeme Bartlett (talk) 03:14, 21 March 2015 (UTC)
The first strikes me as overly specialized and perhaps should be renamed as Carbonyl allylation. The second should be merged into Phenylglyoxal. Boghog (talk) 10:24, 21 March 2015 (UTC)
When I search for the second one, there are very few hits. But the first one has some scholarly work on it. So the addition article could stand alone, but not the second. Graeme Bartlett (talk) 12:16, 21 March 2015 (UTC)
Correct me if I'm wrong, but is the example in first page not simply a tin catalysed Ene reaction? --Project Osprey (talk) 14:11, 21 March 2015 (UTC)

## "carbon fiber"

The usage of is under discussion, see talk:carbon (fiber) -- 65.94.43.89 (talk) 05:06, 22 March 2015 (UTC)

## RFC: Acronym NMR or nuclear magnetic resonance in article titles

The following discussion is closed. Please do not modify it. Subsequent comments should be made on the appropriate discussion page. No further edits should be made to this discussion.

Article titles in Category:Nuclear magnetic resonance are a mix of spelled out (e.g. nuclear magnetic resonance spectroscopy) and acronym (e.g. gradient enhanced NMR spectroscopy). The Manual of Style WP:ACRONYMTITLE says that "acronyms should be used in a page name if the subject is known primarily by its abbreviation and that abbreviation is primarily associated with the subject" and "if readers somewhat familiar with the subject are likely to only recognize the name by its acronym". Should NMR articles always use "NMR", always use "nuclear magnetic resonance", or should use be determined on a case-by-case basis? If case-by-case, what criteria should be used? --Kkmurray (talk) 22:28, 22 March 2015 (UTC)

• Whilst I don't have a strong opinion either way right now, I feel that anyone "somewhat familiar with the subject" would recognize NMR as being nuclear magnetic resonance. It is also worth noting that NMR redirects to nuclear magnetic resonance as well. Lukeno94 (tell Luke off here) 23:11, 22 March 2015 (UTC)
• I'm guessing that the idea behind this is that people are searching for these pages but that few users are going to bother typing 'nuclear magnetic resonance' each time. So yes, seen through that lens page titles should be contracted to NMR where possible. I'm not sure how much that's going help people though; by necessity many of these pages have long and technical titles which could be phrased in a number of different ways, so people might still have difficulty finding what they want. I would suggest that a navigation sidebar might be more helpful, I've attached a draft of what one might look like. Anyone got any thoughts? --Project Osprey (talk) 10:48, 23 March 2015 (UTC)
• NMR. I favor the acronym for simplicity of typing and because it is routinely used and one rarely spells out the acronym. We probably want to have uniformity for the titles of these articles. At least in my circle, we dont say MS for mass spectrum but for NMR, we avoid enunciating those 9 syllables.--Smokefoot (talk) 13:19, 23 March 2015 (UTC)
• I’ll give my own comment here: In general I prefer non-acronym titles - NMR should be spelled out in titles but doesn't need to be spelled out on first use, similar to FM and PC (but note acronyms in FM broadcasting and IBM PC keyboard!). The bar for acronym titles should be high (e.g. DNA, laser, sonar). The current set of redirects takes care of searches and acronym use in articles. That said, there may be a limited number of cases where the acronym makes more sense, for example NMR tube which is not recognizable as nuclear magnetic resonance tube. Another case might be the DAB, as in relaxation (NMR). --Kkmurray (talk) 01:47, 24 March 2015 (UTC)
• NMR for sure. Shorter and easier to type; no other similar acronyms in the field to cause confusion; readers of most of these articles almost surely know what NMR is and don't need it spelled out. Opabinia regalis (talk) 03:53, 24 March 2015 (UTC)
• write out - Reasoning: I tried to see what news sources on internet tend to use, but Google does not really give me a good count on that. I do notice that many news articles do a 'nuclear magnetic resonance (NMR)' in the title or early text, and from then on use NMR. This discussion gets in the direction of 'EEG', 'CPR', 'MRI' and 'ECG' - where the man in the street probably hardly know what these medical abbreviations stand for (and personally I would probably make typos trying to write it out ..), though they know what these techniques do. I see that the medical articles tend to write out the whole all the time, so I guess that I would go for the written out term 'nuclear magnetic resonance' in the article titles and introduction (and immediately introducing the abbreviation NMR as well as after the first wikilink to nuclear magnetic resonance ('Nuclear magnetic resonance (NMR)'), followed by NMR in the remainder of the text. That would then also go in line with MS, E.A. and IR (both for consistency throughout our articles on experimental techniques which are not as strictly pronounced as for NMR) .. For all article titles, the appropriate abbreviated articles need to exist. --Dirk Beetstra T C 05:34, 24 March 2015 (UTC)
• NMR first I think a lot of students (High school) wouldnt recognize nuclear magnetic resonance, second in science articles (also titles) its normally just NMR, and third, Im not sure I would recognize that the article paramagnetic nuclear magnetic resonance spectroscopy was about NMR (all the references in the article use NMR - the article has been moved recently). Christian75 (talk) 14:00, 25 March 2015 (UTC)
• NMR but identify the acronym sometime, somewhere in the article. When I graduated with an undergraduate degree in in Chemistry in 1980, we did not use the acronym...but time changes things. Pretty soon no one will even know what the acronym stands for. Best Regards, 22:18, 28 March 2015 (UTC)
• NRMIt agrees with the manual of style, and is a lot simpler than having to type it out all the time. It should probably say what NRM means somewhere in the article. Rider ranger47 Talk 00:28, 9 April 2015 (UTC)
• I am humble to suggest that full version "Nuclear magnetic resonance" is the one that should be used anywhere and everywhere. My argument is that WP is not to make the things simple for the convenience of people, WP is just an encyclopedia to present the things as they are for all sort of people (expert/non expert) who search the encyclopedia. I agree that most of us, discussing here know well in advance what NMR means in science, but a non-expert would have difficulty to guess. In my view, He should be presented with an info that is precise, full and authentic. I just give an example, have you ever see the prescription slips of the doctors? They dont write the name of medicines in full, and sometime used just some symbols that only a chemist can understand. In due course, their entire community became familiar with those codes, symbols and acronyms etc. For them, it is a routine and probably "Easy" to write the things that way. Just imagine if there is an article on wiki titled "MS Adv++" what one will guess from this? But doctors know that it may either be Multiple Sclerosis in ++ stage, or Marphans Syndrome with ++ abnormalities and so on. A doctor is much happier with this acronym but the same doctor may not even know the meaning of NMR, which is a common term for a researcher/scientist. Thus, I suggest that let it be authentic name and not the one that has become popular in due course or has become known to the researchers in dues course; we have to be friendly with all sort of readers. yes, a seperate explaination page can be created where all possible meaning of NMR (in use at present in various areas) could be placed and let the user (who is only aware of some NMR and not its full version) distribute from there to appropriate article as per his need. And yes, after the first use of full version in title, and in lead, the short version can be introduced, when it appears first in text - that may continue for rest of the article. Educationtemple (talk) 07:29, 13 April 2015 (UTC)
• Spell it out - acronyms are best reserved for things known primarily by the acronym. The bar for this is set quite high, as is the case for DNA, Nato, Laser etc etc. As for related article titles, there should be a case by case discussion to weight out consistency with other considerations in regards to article title. Mbcap (talk) 14:44, 20 April 2015 (UTC)

The discussion above is closed. Please do not modify it. Subsequent comments should be made on the appropriate discussion page. No further edits should be made to this discussion.

## Chemical classes and functional groups

Do we have to split articles to avoid confusion between chemical class and functional group ? For example peroxy acid is about the group -OOH or about the family of all peroxy acids ? Sometimes we are doing the difference like in Alcohol and Hydroxyl, sometimes not. Please look at the page Functional_group (see tables) to see that there is a difference but this difference is not applied in the article structure. Can we define a general trend in order to clear this confusion ?Snipre (talk) 09:42, 23 March 2015 (UTC)

This is a similar issue to sulfate the ion or the compound sulfates. Here there is one article with poor coverage of sulfates. There is a great deal of overlap between functional group and class of coupounds with that functional group. Though if there were two separate articles, the emphasis could differ one on the properties, and one on the diversity of compounds.
If the article is small eg peroxy acid then there is no reason to split. But peroxy acids could talk about the compound class and peroxy acid the group. I have only been making combined articles so far: eg Pentanitratoaluminate, Monofluorophosphate, Tetrafluoroberyllate and Borinic acid. Graeme Bartlett (talk) 00:24, 24 March 2015 (UTC)
Thanks for the comment. Just one question more: how do you think can we name each kind of article. Something like "peroxy acid" for article about the class and "peroxy acid group" for the functional group ?
I was suggesting adding an "s" for the class and no s for the group or ion. It could be confusing though, but so could my suggestion. The word group could mean the functional group, or it could means class of substances. We certainly need to have the main article at the basic name, such as peroxy acid. But what should be the main topic be? Other ideas are peroxy acid functional group or peroxy acid moiety. For some we may need to include the terms "ion" or "radical". For the groups there could be variations though. Could you imagine ether being called ether group? For classes of compounds they may also be called a derivative. Examples where they already differ are seen in the functional group article such as Amide versus Carboxamide, or Thione versus Carbonothioyl — but there seem to be very few. Graeme Bartlett (talk) 21:35, 26 March 2015 (UTC)

## chemeo.com

A number of IPs have been adding links to chemeo.com to chemistry articles:

...and maybe others. Is there consensus that this is a useful link? The fact that the editor adds two links and then switches IPs suggests they believe they are doing something wrong and want to avoid detection. ChemNerd (talk) 11:48, 24 March 2015 (UTC)

I see that Materialscientist has now reverted all these additions, so perhaps the question is moot now unless the user returns. ChemNerd (talk) 13:41, 24 March 2015 (UTC)
The linked pages seem to be come kind of information aggregation, surprisingly free from advertisements like other similar pages around. But not adding any more than we would expect from our infobox content. Perhaps the person doing this is Loïc d'Anterroches the software writing consultant behind Céondo. If he does not have enough to do perhaps we ask him to do something useful on Wikipedia in this project. Graeme Bartlett (talk) 20:57, 24 March 2015 (UTC)
Yes, and Edgar181 too. I see no reason why linking to chemeo.com instead of the few databases they copy (like NIST Webbook). Besides, we can not guarantee that chemeo.com will remain accurate, stable and spam free - they come from ceondo.com, which states on their front page: "Céondo, custom scientific software development and services for the oil & gas, chemical, pharmaceutical and crop science industries. Since 2007, we are really good at converting your models into easy to use software." Materialscientist (talk) 02:50, 25 March 2015 (UTC)
@ChemNerd: The fact that the editor switches IPs suggests to me nothing more than that they are on a connection with a Dynamic IP address. Please assume good fiath. Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 14:07, 25 March 2015 (UTC)

Hello, I was the author of the links and I am author of Cheméo. I added something like 10 links in total, nothing more, always trying to add a link when it brings something. With respect to the difference with the infobox content, as a chemical engineer, you really need all the values with uncertainties when doing regressions, this is why it brings something to the users (also the data are available as Excel file, which is quite nice). My question, and this is a genuine question, can Wikipedia become a place where the kind of data we need as chemical engineer is available (and I would be glad to setup export options from Cheméo to a Wikipedia compatible format) or should we say, no, this is not the place and we even consider a link from Wikipedia to a website like Cheméo equivalent to spamming? If you consider it as spam, I can take the referrer logs of Cheméo to find all the links and remove them. I have no problems with it, I enjoy the quality of Wikipedia every single day, so I will never do something considered unwelcome by the community, but again, I would be glad to contribute! (Note, I created the ChemMeyer account right now, the change of IP addresses in the edit were just because I have a simple DSL connection, I did not try to avoid dectection) ChemMeyer (talk) 08:11, 25 March 2015 (UTC)

Perhaps ChemMeyer you can look at the chembox parameters that we have on each article and fill in the missing data, with referencing to reliable sources for that data. If there are fields in the chembox missing for certain classes of data then let us discuss it here or at Wikipedia talk:Chemical infobox. You could propose some extra quality standards in addition to the little green ticks. Graeme Bartlett (talk) 11:20, 25 March 2015 (UTC)
First, thank you for the very positive tone, even after my by break of the Terms of use. My "problem" so to speak with the chembox is that it is missing the uncertainty on the values. For example, just take the www.chemeo.com/cid/45-400-7/Octane if you look at the critical pressure, you cannot really "put" a value on it, as we have a lot of different measurements, each with a given uncertainty, here from 24.7 to 24.9712 kPa for the measurements. So, you can put a range (this is the case for the standard enthalphy of combustion on Octane) but you lose a lot of information. Is the range the upper/lower bounds of an average with +/- 1 or 2 std deviation? Is the range the "raw" range of the measurements? Is the upper value the upper measurement + the uncertainty or just the upper measurement? So, maybe I should write a document on "how to select/calculate" the "best value" for a compound property based on measurements and discuss it with you at Wikipedia talk:Chemical infobox. But as every single scientist has a different idea on the subject, chemeo is there to just provide the raw data in an easy to ingest way. The "traditional" use of the data is to use all the data in the regressions with a weighted regression using the uncertainty of each data point to weight the value. I hope this comment helps you understanding my background and why the work on Cheméo (I suffered not having this kind of data during my PhD) ChemMeyer (talk) 12:04, 25 March 2015 (UTC)
I like the option to list all C
6
H
6
O
2
: [1]. A category in wiki? ChemMeyer, since your data sheets are more elaborate and complete in their topic, what do you mean by "I enjoy the quality of Wikipedia every single day"? -DePiep (talk) 12:16, 25 March 2015 (UTC)
I enjoy the quality of Wikipedia on many subjects (I often put "wikipedia" in my Google search when looking for something), this is why I do not want to do something which could affect badly the community behind it and if I can contribute positively, I will do it. ChemMeyer (talk) 12:58, 25 March 2015 (UTC)
To be clear, I intended to ask an open question, not checking your faith ;-). IMO the quality of the chemeo data sheet is higher than {{Chembox}} (especially in certain aspects), so I was looking what you learned from wiki. Consider answered. -DePiep (talk) 13:14, 25 March 2015 (UTC)
The chembox is also providing a lot of contextual information not available on cheméo. If you want the odor of substance, etc. Wikipedia has it. So, for some domains, the chembox is definitely better. I am a process/chemical engineer too, so it means that all the medical properties are a bit excluded from the data I collect as I cannot assess their quality. ChemMeyer (talk) 13:26, 25 March 2015 (UTC)
Try enter C6H6O2 into the search box (or press here: C6H6O2) Christian75 (talk) 12:41, 25 March 2015 (UTC)
Nice Category:Molecular formula set index pages. Sets are up to date? Link from chembox? -DePiep (talk) 12:52, 25 March 2015 (UTC)

### Categories for molecules

The above discussion raises an interesting point. If we use categories like Category:C10 molecules, Category:H14 molecules, etc., then it should be possible to query category intersections to find all C10H14... molecule articles. Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 14:07, 25 March 2015 (UTC)

"Query category intersections" is a years-old feature request. There are third-party or wmlabs tools that do it (WP:CATSCAN for example). DMacks (talk) 15:02, 25 March 2015 (UTC)
While category crossing is core of the wikipedia cat principle, such querying is slow, cumbersome programming and not available for readers (compare: search box). Is why we are still using categfories like "American scientist" (which, in this, should be split).
wrt this specific idea, to name category like :Category:H14 molecules, the naming in itself is not meaningful. So it would be a more theoretical tree (while logically sound). Using existing set lists such as article page C6H6O2 is one other route (takes more manual maintenance); and before knowing about these setlists I had thought of :Category:C6H6O2. -DePiep (talk) 15:39, 25 March 2015 (UTC)

## Paper: Wikipedia Chemical Structure Explorer

I've just been made aware of:

Wikipedia Chemical Structure Explorer: substructure and similarity searching of molecules from Wikipedia
Peter Ertl, Luc Patiny, Thomas Sander, Christian Rufener and Michaël Zasso
Journal of Cheminformatics 2015, 7:10
doi:10.1186/s13321-015-0061-y

-- Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 15:54, 25 March 2015 (UTC)

[2]. Wow. -DePiep (talk) 16:02, 25 March 2015 (UTC)
The website is here. User:Mzasso was apparently involved in the development of this tool. -- Ed (Edgar181) 16:26, 25 March 2015 (UTC)
I am 'visiting' WP:CHEM ~one year by now, mostly editing templates. I am not a chemicalitycist. I am surprised that: 1. chemistry is so well organised and well working on the web, 2. that there is little development in our {{Chembox}} & {{Drugbox}} data setups. For example, only recently we can split CAS RN's over multiples in one {{Chembox}}. I am working these templates, but rarely I see suggestions for improvements (by flaming requests!). Shouldn't/couldn't enwiki be the #1 spot for 15000 chemicals? Didn't this cheminfo.org have one suggestion for improvement? -DePiep (talk) 22:14, 25 March 2015 (UTC)
I suppose this should motivate us to try to fix errors, merge synomym or alternate spelling pages. Also if people are building tools to use the infoboxes, it means we will cause chaos if we change the structure! Graeme Bartlett (talk) 03:13, 26 March 2015 (UTC)
This is great! Nice work, Mzasso et al!
I imagine the pyrrole errors must have originated in some upstream tool used to generate the SMILES strings. Those should be easy to fix.
DePiep, I'm not sure what suggestions you're looking for, but one thing this data suggests is that SMILES strings in wikitext are fragile. The largest source of errors is likely to be just drawing mistakes, but since SMILES strings are text, they're editable just like everything else on the page and therefore subject to copy/paste errors, typos, undetected vandalism, etc. I am new to the whole wikidata thing but that seems like the obvious place to store this kind of data, no?
Any why stop at 15,000? Import everything with a literature annotation from ZINC? ;) Opabinia regalis (talk) 04:16, 26 March 2015 (UTC)
Opabinia regalis, I'm looking for major directions & inspirations for {Chembox}: merge with {Drugbox}?, rebuild in Lua asap?, verify the fields?, re-organise extra links?, connect with wikidata?, etcetera. Last years, development has stalled imo. -DePiep (talk) 11:57, 26 March 2015 (UTC)
SMILES seems to fail pretty badly for non-classical bonding such as transition-metal complexes. Ferrocene is one of the simplest of these pathological cases. A long-term gripe of mine is using them to generate the JSMol 3D images that are really high quality images of sometimes complete chemical nonsense. DMacks (talk) 04:35, 26 March 2015 (UTC)
Fails it on Wikipedia or in general? (I have no experience with SMILES). Christian75 (talk) 09:37, 26 March 2015 (UTC)
The problem with Wikidata is that "nobody" sees your edit (I think they are planing to add edits to your watchlist, but not articles), and its very diffucult to figure out where to edit the field in the infobox (no view/edit button). Christian75 (talk) 09:37, 26 March 2015 (UTC)
AIUI, a fix for the latter issue is in hand. Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 10:23, 26 March 2015 (UTC)
The majority of the data that wikidata collects seems to be ID numbers for other databases (i.e. CAS, Chemspider, Pubchem, ENICS etc), the entries for chemicals contain very little of what we as chemists would consider to be the key data (bpt, mpt, solubility etc). --Project Osprey (talk) 10:59, 26 March 2015 (UTC)
The problem is that WD is under development and we miss the quantity datatype with unit: you can add numbers but you can't add unit. So all data about physical or biological properties are not yet implemented but they are already planned (see d:Wikidata:WikiProject_Chemistry/Properties). The quantity datatype with unit should be available this year around June-July according to development progress for WD. Snipre (talk) 11:09, 26 March 2015 (UTC)
I do not use my watchlist to review edits for chemistry/chemical articles but the history of the article and Special:Contributions. I do not think you have to activate it [wikidata in your watchlist] (mine was activated). I tried to change a wikidata image, and added a article which used it (via WikiData) on my watchlist, but it didnt seem to work (but it look like they are working at it phab:T90435). Nice if the infoboxes gets a button to edit the "properties" on wikidata (Do you have a link to the module? I havent seen it used anywere). Christian75 (talk) 11:16, 26 March 2015 (UTC)
I had to check the option to have my watchlist able to follow WD edits. Better to do it. For the direct link in the infobox to the WD item, I can just give you an example: go to the hungary WP, for example hu:Lyon and look at the population data (Teljes népesség in the infobox). You can see a ± symbol after the reference anchor, this is the link to the population property in the WD item for Lyon. Snipre (talk) 12:50, 26 March 2015 (UTC)
Thanks, its done with hu:Modul:Wikidata (search for "+/-") Christian75 (talk) 13:12, 26 March 2015 (UTC) btw: its only for population it has a +/-. a lot of data in that infobox are from wikidata (the all the images, Ország, INSEE-kód, Irányítószám, Testvérvárosok, time zone (Időzóna), the map and the coordinates. (but it could be fixed by templates) Christian75 (talk) 13:21, 26 March 2015 (UTC)

I'm just a lay editor, I don't know how to change templates or add things to wikidata, even chembox validation confuses me (am I supposed to be turning those crosses to ticks somehow?) but even I can see advantages to this. The fact that it shows structures related to what you're searching for should allow us to tighten-up our categories and find orphan compounds, plus mass error checking for SMILES and other parameters. It's got me thinking though; we've got 15,000 compounds and we're trying to organize them via the use of categories or 'see also' sections, chembox data is still largely checked manually, it just seems woefully insufficient. Perhaps we could try and recruit Mzasso? DePiep is probably right, Mzasso is likely to have ideas on how we could better curate our database and I would be interested to hear what they are. --Project Osprey (talk) 10:34, 26 March 2015 (UTC)

I am contributor on WD so I can't be fair but the first step to create a secured database is to have ... a database. Right now data in articles are not correctly monitored because the access to this data is difficult: you have to extract the data from the wikitext and this a mess because data are mixed with formatting code. So by creating a real database you can run automatic tools to check modifications and to compare periodically the content with other databases in order to ensure a correct data set. Snipre (talk) 11:02, 26 March 2015 (UTC)
Sorry, that wasn't fair of me, I know people are trying to fix this. Is the data in the chembox more machine readable as the values are better defined? --Project Osprey (talk) 11:08, 26 March 2015 (UTC)
This is a problem of parsing: in chembox you mix number and string for one data. The value and the unit. Each time you have to extract this kind of information from the wikitext and that is dependent on the way people write the data in the infobox. If you have a structured database, you avoid this extraction step and you eliminate the problem of bad formatted data. If you can format all values in chembox according to the same pattern, yes you will have a better machine readable infobox, but this is not possible because not all contributors are familiar with editing rules. Snipre (talk) 12:58, 26 March 2015 (UTC)
Snipre, this I do not get. For two years already. What on earth can enwiki editors (including template& Lua editors like me) do to improve this WD-support for chemicals? One never reads such a task/request. (is there a bot that already scraped CAS RN and PubChem id's from our 15k templated chem articles?) -DePiep (talk) 21:10, 26 March 2015 (UTC)
DePiep If you want to know how you can help look at d:Wikidata:WikiProject_Chemistry/ChemID. Right now we use Q number (WD identifiers) to connect articles between different WP but who checks that the links were build with the good articles ? Snipre (talk) 06:41, 27 March 2015 (UTC)
re Snipre Shouldn't that 'who checks'-question be answered five years ago when wikidata was designed?
You write about "The value and the unit". I note that, by SI definition, the wording is: "value = number × unit", eg "length = 5 m". It is algebraic (it's SI-legal to write: "value / unit = number"). I hope WD wants to use this right from the start. (To solve: "value" in database is not "value" in SI; it's more like data vs datatype I guess). mistake -DePiep (talk) 07:38, 30 March 2015 (UTC)
DePiep That is the choice of each WP to use WD or not for linking articles and as each WP is free to decide how to split articles according to subjects, this is their task to select the corresponding articles in others languages. WD is a tool and can't decide if an article about a stereoisomer can be linked to another article about the racemic. Each WP can have its own rules, the question is just to know if they are inside each WP rules or recommendations to treat that question.
For the question of value I think you find yourself the answer. But please consider that a value can be something different than a number and a unit. WD manages strings, numbers, URL,... So SI definitions can't be applied straightforward. Snipre (talk) 08:27, 30 March 2015 (UTC)
I'm saying that the Database Universum should change the word "value" (meaning something like: a single field input). I do state that you should not change the SI-wording that is "value = number × unit" when discussing that datatype (then again, writing: "the datatype for measurement is structured `value × unit`" does not solve it does it). It's up to WD people to find a solution. mistake. -DePiep (talk) 08:37, 30 March 2015 (UTC)
My mistake. SI base unit uses this wording: quantity = number × unit (as in: length = 5 m). No ambiguous meaning in here. The wikidata `datatype` could be quantity then? Note 1: outside of SI anything can happen, eg pounds and long tons. Note 2: in SI parlance, the word "value" is used this way: "The value of a quantity is generally expressed as the product of a number and a unit".Brochure, Chapter 1. That nicely would be the content of that data field, right? I apologise for this misleading mistake. @Snipre:. -DePiep (talk) 08:35, 2 April 2015 (UTC)
• A short discussion with Andy Mabbett invited me to add the wikidata reference to the compounds on chemeo.com. Once the link wikidata <-> chemeo id is there, I can easily provide a way to generate a read to "paste" data page with the data I have collected. I could also create a small crawler doing a check between the information I have and the info in the chembox to help spot the errors. ChemMeyer (talk) 20:12, 26 March 2015 (UTC)
Or you can export your data in WD. Please have a look at d:Help:Sources to have an idea about the structure of source data. This will ensure a future automatic way to generate references in the WP articles. Currently data with units can't be added. The quantity datatype with unit will be implemented in the next months but not definitive date is given (see this). Snipre (talk) 21:36, 26 March 2015 (UTC)
Ideally Wikipedia should have a chemical registration system based on a unique identifier that would prevent unintentional content forks. Canonical SMILES works pretty well for organics but apparently not so well for transition-metal complexes. InChI may be an alternative. All other chemical identifiers (e.g., CAS Registry Number, PubChem ID, chemeo id. etc.) should be linked to the structure as defined by the Canonical SMILES or InChI. Sanity checks between the SMILES/InChI and external IDs could be run by bots. (User:BogBot did a limited amount of this type of checking on {{Infobox drug}} here). Boghog (talk) 21:54, 26 March 2015 (UTC)
@DMacks: Is the SMILES problem with transition-metal complexes inherent to SMILES or the software that was used to generate the SMILES? Obviously the later can be fixed whereas the former cannot. Boghog (talk) 22:14, 26 March 2015 (UTC)
I tried feeding ferrocene to molconvert and didn't get anything usable, so it's not just JSMol. I imagine the problem is these tools are failing at figuring out the coordination geometry, which the SMILES string alone doesn't say much about. I agree there should be one canonical unique identifier used to key the rest of the data, but is the best way to sanity-check data here, or to (eventually) move it to wikidata and use that to populate the local infoboxes? Seems like the data is that way less susceptible to text degradation, and would need less frequent bot-validation. Either way, DePiep - seems like verification is first priority, wikidata migration when possible (I mentioned I was new to the whole idea, I would never have thought units would be a limitation!). Opabinia regalis (talk) 05:06, 27 March 2015 (UTC)
The SMILES is limited, it was developed for organic chemistry considering only the connectivity between atoms and with the time "patched" to express better the complexity of the molecules. It is very good to find all the nearly identical molecules and in nearly all the cases you have a unique "canonical" SMILES for the molecule. But you have too many conflicts to use it as unique identifier. The InChI key in format: TVMXDCGIABBOFY-UHFFFAOYSA-N is a special hash and can conflict too. The full InChI is what is at the moment considered the best unique identifier derived from the molecular structure. Usually as a database curator, you try to use all the identifiers you have about a molecule and use heuristics to merge the records in your database. This is of course error prone. (Side note, yes I will try to push data into Wikidata once the units etc. are there) ChemMeyer (talk) 08:43, 27 March 2015 (UTC)

As coauthors of this paper Michael Zasso and me (Lpatiny) have thanks to this tool corrected many mistakes in SMILES that were present in wikipedia. Our idea behind this tool is to increase the search possibilities of wikipedia and we have therefore make everything open source under a BSD license and a system allowing a nightly automatic updates (with update of the github repository). Up to know wikipedia queries capabilities are relatively limited and here we can provide a new way to search for chemicals. One of the original idea is that the substructure search engine is in the client browser and not on the server ! This means that you don't actually need any intelligence on the server and it allows to make interactive substructure search that was not available on the internet up to know (even offline !). We invested a lot of effort to create this tool and we are wondering if you could consider changing the chembox / drugbox to add a search capability directly in the box (small magnifier) that would point to our website or any other website that could fork our project. Lpatiny (talk) 21:54, 27 March 2015 (UTC)

@Lpatiny: A small question: why do you use WP and not PubChem which offers you the possibility to perform research on a more larger dataset ? Then why do you restrict to only one WP like en:WP and not working with de:WP or with a merged set of these two WPs ? Snipre (talk) 14:25, 28 March 2015 (UTC)
1) I think a link to this tool allowing search by structure would be really useful for readers (who are, by hypothesis, already on WP and not on PubChem).
2) Have you considered doing something like clustering the WP entries, comparing to pubchem, and reporting back which areas of chemical space are underrepresented on WP? Opabinia regalis (talk) 20:35, 28 March 2015 (UTC)
Opabinia regalis I am working on something similar using data from en, de and fr:WP. I create an unique list using WD ID in order to compare data from the 3 WPs. Results are there and first analysis there. Snipre (talk) 21:16, 28 March 2015 (UTC)
Thanks, will take a look! Opabinia regalis (talk) 03:35, 30 March 2015 (UTC)
@Snipre: We are thinking that wikipedia could somehow replace the merck index. Just some important molecules that are well described. This is the kind of "small" set of interesting molecules for which we can provide on the fly structure browsing. This would not be possible with PubChem (we would not be able to load all the structures in the browser !). Lpatiny (talk) 09:15, 30 March 2015 (UTC)
If would indeed be a good idea to give a list of products that are described in wikipedia but either don't have a chembox / drugbox. This could be done by searching the huge list of names present in PubChem to check if there is missing information. We never tried to do this. However for all the products that have a drugbox / chembox but no SMILES we have a report on the error page that is called "not found". Just go on http://www.cheminfo.org/wikipedia and click on "Browse errors" to get the list. Lpatiny (talk) 09:15, 30 March 2015 (UTC)

@Lpatiny: Have you considered including other language versions of Wikipedia, e.g. de.wikipedia or fr.wikipedia? The former does not have the SMILES code in the chembox, but assigning would be possible via Wikidata or the PubChem ID. --Leyo 19:01, 30 March 2015 (UTC)

@Leyo: We didn't think about it before but received a lot of requests for it (fr and de). We are considering hiring an internship here in Lausanne (Switzerland) to reconsider the system, use Wikidata and have it is all available languages as well as providing more searching possibilities. If anybody is interested in this project please contact me. We have some interesting demonstration of our system on http://www.cheminfo.org and there are a lot of functionalities we would like to add using the wikipedia data Lpatiny (talk) 07:27, 1 April 2015 (UTC)

## New article at AfC

Greetings. We have an article over at AfC, which appears to be copacetic, but I am definitely not a chemistry person. Could someone from this project take a look at either ping me, or respond here? Here's the link to the article. Much appreciated. Onel5969 (talk) 21:11, 29 March 2015 (UTC)

@Onel5969: This looks like homework. There's been a rash of that lately in bio/chem articles and the username is consistent with the other ones I've seen. The structure and reactions sections look okay on a quick skim; the applications section presents a lot of proposed/prototyped applications, but the TOC heading and text tend to give the impression that they're in active use. These are statements about research, not in the core of the WP:MEDRS scope, but some of the medical-flavored claims still need a lot of toning down, especially the adenosine section. Opabinia regalis (talk) 03:54, 30 March 2015 (UTC)
It's a legitimate compound already mentioned at Boranes and Caesium dodecaborate. That said the article could do with a lot of thinning-out; the compound is more-or-less just of theoretical interest and doesn't have any real world applications yet. --Project Osprey (talk) 09:04, 30 March 2015 (UTC)
Thanks Opabinia regalis and Project Osprey - Based on your comments, I'm going to decline the article, stating that it's not written in an encyclopedic tone. Then, unless you object, I am going to share some of the things you've said (without naming you), to give the editor some direction. Onel5969 (talk) 12:42, 30 March 2015 (UTC)
Well I think that you are too late, despite the pre-existing solid articles cited by Osprey. This kind mediocrity makes Wikipedia look silly and means more work for others. --Smokefoot (talk) 13:24, 30 March 2015 (UTC)
Seems you are right, Smokefoot - Different editors have different ways of seeing things. I had hoped to be a little more pro-active about this article (like I try to be regarding math articles), and ask for help from the project, but Graeme Bartlett, who is a very good editor, saw it otherwise. Anyway, thank you all for taking the time to respond. Onel5969 (talk) 14:12, 30 March 2015 (UTC)
Sorry about causing chaos here. I moved it to dodecaborate. It was just about the oldest unreviewed AFC page. My findings are that the article is a bit of a blend of information different substances, including a borane that does not seem to have been made, two kinds of ion, one exotic, and one quite real, and a carborane. The carborane writings might be able to go in a different article. We did have a need for an article on dodecaborate rather than just a redirect. We can continue with the idea to merge with Caesium dodecaborate. Graeme Bartlett (talk) 21:03, 30 March 2015 (UTC)

## Changing Molecular formula to Chemical formula in chembox

I suggest changing "Molecular formula" to "Chemical formula" in {{Chembox Formula}} (the chembox), it is used for salts too - like Sodium chloride. Right now, its a piped redirect to chemical formula e.g. [[Chemical formula|Molecular formula]] which I propose should be changed to [[Chemical formula]]. There is one objection aginst this change, please comment at Wikipedia_talk:Chemical_infobox#Changing_Molecular_formula_to_Chemical_formula Christian75 (talk) 17:26, 30 March 2015 (UTC)

## Hybrid vapour phase epitaxy

If anyone could help with this article, I'd be grateful. It's been tagged for notability, and many other issues, for 7 years. Best wishes, Boleyn (talk) 08:03, 31 March 2015 (UTC)

## Template:Oxygen compounds, Template:Nitrogen compounds and others

Due to the arbitrary selection (and necessary incomplete listing) such navigation templates are completely useless IMO. Or is there a project guideline that supports them? --Leyo 08:53, 4 April 2015 (UTC)

I doubt their usefulness in articles. First of all, Category:Nitrogen compounds should cover this. OTOH, why not add this template to that category (and rm from articles)? It shows alternative identifiers (by formula), and has redlinks for those who are searching. Complementary to the category list, I'd say.-DePiep (talk) 09:10, 4 April 2015 (UTC)
Because of incompleteness it would be better to just link to families, eg there is already a template:nitrates, perhaps we could have templates for nitrides, and amines and amides. And then there are all the biomolecules with oxygen and nitrogen we can't expect to navigate. There is already a Template:Oxides, and some like Template:Oxides of carbon, but really you can't expect to link to all the oxygen compounds in a navigation box. The closest we could do would be just to link to the family members in a nav template. Graeme Bartlett (talk) 09:39, 4 April 2015 (UTC)
(edit conflict) It has been TfD in 2011 Wikipedia:Templates_for_discussion/Log/2011_August_16#Template:Rubidium_compounds (no consensus) - personally I found them usefull because its easy to navigate between related simple compounds of an element (which isnt possible with categories) - but some of these templates need some cleanup. An inclusion criteria could be that they are described in elementary chemistry books. Some of the templates are more organized, like Template:Molybdenum_compounds, and Template:Ruthenium_compounds. Christian75 (talk) 09:42, 4 April 2015 (UTC)
Your examples are actually useful because Wikipedia does not have so many articles on these element compounds, but the oxygena dn itrogen templates are still quite new, and have too many candidates to cover properly. So where there is a reasonable representation of what you might want to navigate to, then this is useful. But I don't think reproducing oxides in an oxygen compound template adds anything useful. Graeme Bartlett (talk) 10:45, 4 April 2015 (UTC)

## Astatine FAC

Hi! The article astatine has been at FAC for quite some time now, and the process could really use some more input. If you could take some time to come in, please give it a look. Unfortunately, the daughter WP:ELEMENTS is very small and can't really organize a high number of editors who could come in. Any effort, positive or negative, would be much appreciated, and, if you wish, a favor in return is on me.--R8R (talk) 10:02, 6 April 2015 (UTC)

## Haber Process

An editor with strong views on political and technical history has overhauled large portions of Haber Process. IMHO, these edits are soap-boxy, so it would be good if others helped out. I tried to slow down the process but was quickly dismissed, indicating at an article ownership issue. Ideally, we would revert all and then the proposed changes would be discussed on the Talk page so that we can achieve consensus. The article is heavily consulted, being viewed 22,000 times last month alone.--Smokefoot (talk) 13:02, 7 April 2015 (UTC)

The additions are more than a little preachy (and wordy). There is some interesting history that could be added though, the Treaty of Versailles compelled BASF to license the Haber process to the French and the British managed to get them to sub-license it to ICI, so it was something of big deal politically. A lot of the other information could be cleaned up and moved over to Haber's page --Project Osprey (talk) 13:55, 7 April 2015 (UTC)

## Pyrazolone

Do the text and structures in pyrazolone actually describe dihydropyrazolones (or pyrazolinones)? See PubChem 11513733 for pyrazol-3-one. ChemNerd (talk) 18:53, 8 April 2015 (UTC)

Oh, you need to get a card-carrying organic chemist for that info, i.e. Edgar. --Smokefoot (talk) 22:39, 8 April 2015 (UTC)
I'm no Edgar, but I do have access to chemical databases. Scifinder resolves 3-pyrazolone and 1,2-dihydro-pyrazol-3-one to the same structure. It would seem that pyrazolone is used as a common name and 1,2-dihydropyrazolone is the IUPAC name; the Hantzsch–Widman nomenclature can become really confusing once you start substituting things so this might just be an historic cock-up. In any event searches using the IUPAC name get better results, which does make sense. Scifinder resolves pyrazolinone as the ring saturated compound (so the ketone of pyrazolidine, CASNo 27274-34-6), it's very rare in the literature and if you drop that CASNo into pubchem you get a different structure PubChem 351317 so there may be some confusion regarding that. Best I can do I'm afraid --Project Osprey (talk) 09:54, 9 April 2015 (UTC)
I agree with Project Osprey. "Pyrazolone" is a chemical name that is used ambiguously. The structures described in pyrazolone are technically better named as dihydropyrazolones, but the term "pyrazolone" is commonly used for the related compounds with any degree of saturation. -- Ed (Edgar181) 12:09, 10 April 2015 (UTC)

## Wikipedia talk:Articles for creation/Heterogeneous Catalytic Reactors

Dear chemistry experts: One more old AfC draft to consider before it is deleted. Is this a notable topic? Should it be improved, or let go? —Anne Delong (talk) 05:22, 9 April 2015 (UTC)

I'd say let it go. It's a subset of reactor design...viable topics would be the parent idea of reactor design and the child ideas of each individual reactor design. The sole claim of notability for this specific subset ("one of the most commonly utilized reactors in the chemical engineering industry") seems pretty weak: yhe only other possible types seem like they would be "homogeneous" or "non-catalytic", and those are also very popular. We do have articles about at least some of the specific types and some of the specific reactions mentioned (with cites), and they do not completely agree with the article here (what type of reactor is used in a certain context, what the flow characteristics are). DMacks (talk) 05:38, 9 April 2015 (UTC)
Thanks, DMacks. I have deleted it under db-g13. It can always be refunded if someone in the future decides that the topic has become notable, or wants to make a redirect out of it.—Anne Delong (talk) 02:18, 10 April 2015 (UTC)

## Who?

Which editor posted that serious question I'd like to reply to? Was it at Chemistry, Chemicals, Chembox, Drugbox, Chem infobox, xxx? -DePiep (talk) 22:15, 12 April 2015 (UTC)

## drugfuture.com

We currently have a bunch of links to drugfuture.com (see [3]). I think this website is just hosting content stolen from elsewhere such as Merck Index. Can anyone who has access to Merck Index please check? If the website is hosting copyrighted material, since Wikipedia:Copyrights says, "if you know or reasonably suspect that an external Web site is carrying a work in violation of the creator's copyright, do not link to that copy of the work", we should either retarget the links to the original source or remove the links. ChemNerd (talk) 17:25, 13 April 2015 (UTC)

## Flame retardant#California's fire safety laws

Sandcherry moved parts of the Chemtura article to Flame retardant#California's fire safety laws. The text does not seem to always be neutral. I am thinking of phrases such as `Blum appears to be unable to accommodate the views of other scientists and fire-safety experts`. I would appreciate if a native English speaker could go through the text. --Leyo 00:28, 14 April 2015 (UTC)

That section is pretty awful. Just deleting the whole section would be my recommendation. The style furthers the tradition of Wikipedia being a forum for a lot "hippie science." --Smokefoot (talk) 13:25, 14 April 2015 (UTC)
I disagree on deleting the whole section. The topic is of high importance. --Leyo 14:33, 14 April 2015 (UTC)
The article is generally "awful" and needs a lot of work (trimming!) particularly the material moved from Chemtura. I will edit it as time permits. Cheers! Sandcherry (talk) 23:38, 24 April 2015 (UTC)
Sandcherry, trimming is a good description of what needs to be done. --Leyo 19:12, 25 April 2015 (UTC)
Better? Sandcherry (talk) 04:07, 4 May 2015 (UTC)

Hello, chemists. While browsing in Draft space I came across these, in case anyone is interested:

Anne Delong (talk) 14:55, 17 April 2015 (UTC)

Some thoughts:
Draft:Division of Organic Chemistry of the American Chemical Society - I don't think it is notable on its own, but content could be merged into American Chemical Society.
Draft:Total synthesis of Mesembrine has already been merged into Mesembrine.
Draft:1P-LSD is a copy of the article that was deleted at Wikipedia:Articles for deletion/1-propionyl-lysergic acid. It would qualify for WP:CSD#G4 if moved to article space in its current state.
Draft:1,2-addition of allylmetal compounds to carbonyl groups could be merged into Allyl#Allylation, or split out into a separate article at Allylation (currently a redirect).
-- Ed (Edgar181) 20:35, 17 April 2015 (UTC)
Ed: Thanks for taking the time to check these out.
• (1) The American Chemical Society apparently has 32 of these divisions. What if I start a section called "Divisions", add a short summary of this division (a couple of sentences), and then move the draft to Division of Organic Chemistry of the American Chemical Society as a redirect pointing to this section? If I move the whole draft it will overbalance the article, and besides, some of it is similar to material in the main article
• (2) I moved the redirected draft to Total synthesis of mesembrine and added the appropriate merge templates on the talk pages, so that should be all done.
• (3) It appears that you are the one who has recreated this, so I'll leave it for you to work on, although from the comments in the deletion discussion there doesn't seem to be much hope.
• (6) This would need to be done by someone who knows the subject. I can help with the technical parts if necessary.
• (4) and (5) Maybe someone else would like to comment on these two. —Anne Delong (talk) 16:23, 21 April 2015 (UTC)
#4 looks OK to me, with some formatting fixes. You might get better insight on #5 at WT:MED since this is a clinical chemistry issue - my first thought is to merge to Isotonic hyponatremia#Pseudohyponatremia with a redirect at electrolyte exclusion effect.
Selective merge sounds right for #1. This is by a good margin the largest of the ACS divisions with some 15,000 members, so it's not too unbalanced to have a lot of information about it. Opabinia regalis (talk) 20:35, 21 April 2015 (UTC)
Opabinia regalis, a concern has been raised on the draft that the references are all from the same researchers. Some other sources have been found and added as general references. Can you move these into the article as citations to replace or suppliment the ones which may be too primary?—Anne Delong (talk) 01:39, 22 April 2015 (UTC)
you cannot replace the original citations with general references, the original authors have based their edits on these original citations. General references if relevant can always be added and supplement the article. The (peer-reviewed) primary sources are important for fact checking and validation via the article summary, secondary / general sources are usually difficult to access (paywall, not available in library). V8rik (talk) 16:36, 22 April 2015 (UTC)
Will look later tonight. Haven't had a chance to look at the papers in detail here, but agreed in the general case that Wikipedia's use of the term primary sources to refer to both peer-reviewed literature and fluff like press releases and blogs can be a problem. Opabinia regalis (talk) 19:32, 22 April 2015 (UTC)
Done, I'll leave the processing to you. I'm pretty sure I left templates scattered all over last time I tried to manually accept an AfC draft! Opabinia regalis (talk) 01:45, 23 April 2015 (UTC)
Yes, the AfC Helper Script really makes it simpler. It's in mainspace now at Diffusive gradients in thin films. I agree that general references which can't be read because of paywalls can't accurately be made into citations. I'm surprised, though, to see V8rik write that general references are not in libraries; in my experience it's the other way around, and the journal articles are the ones behind paywalls, while textbooks and science magazines are more accessible. That's likely because I'm not a scientist, so I don't have the usual subscriptions. I also agree that primary peer reviewed sources are better sources than blogs and personal websites for facts, although studies have been known to contain errors, so more than one such source is better. However, it's what the secondary sources say about a topic that demonstrates notability and acceptance by the scientific community, so it's good to have some of these too. Anyway, thanks to all who helped out here; I'll get to work on the society article in the morning.—Anne Delong (talk) 03:17, 23 April 2015 (UTC)
Note 1. Depends on your library and your library privileges? In my library I have access to all the electronic journals and a collection of general reference books but access to just any book is out of the question. Note 2. If the original author of the article is willing to replace references who am I to complain V8rik (talk) 21:52, 23 April 2015 (UTC)
I'm not the original author, who is seemingly long gone, but in this case it turns out that one of the sources recommended by the reviewer (the INAP white paper) is free, comprehensive, and relatively easy to read, so it's an effective addition to subscription-only journal sources. In general I'm not in favor of this pattern of presenting the most important distinction in sources as 'primary' vs 'secondary', rather than the quality of the evidence presented. Opabinia regalis (talk) 02:05, 24 April 2015 (UTC)
Moved allylmetal page to allyl V8rik (talk) 14:47, 26 April 2015 (UTC)
Thanks, V8rik. I moved the redirect to Carbonyl allylation, which I hope was an appropriate title, and added the usual attribution templates, so that's another one completed!—Anne Delong (talk) 01:46, 27 April 2015 (UTC)

## suggested COI edits at Dow Corning

Hi, I've proposed some additions to Dow Corning on the article's Talk page, here. I'm not editing directly because I have a COI (I work for a communications firm that represents Dow Corning), but if anyone here is interested in taking a look and providing feedback, I'd be really grateful. Thank you! Mary Gaulke (talk) 16:28, 20 April 2015 (UTC)

Thanks for being upfront and going about this the right way. --99of9 (talk) 22:26, 24 April 2015 (UTC)

## Chemistry societies navbox

I have created {{Chemistry societies}}; it should be deployed to each of the articles it lists, shortly. Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 09:43, 21 April 2015 (UTC)

Great. We need an article on the Federation of Asian Chemical Societies (FACS). There are plenty of articles that mention it. It would then be added to this navbox. --Bduke (Discussion) 10:03, 21 April 2015 (UTC)
Indeed. I've added that to the (long) list of red links for chemistry societies, at Wikipedia:GLAM/Royal Society of Chemistry#Organisations. Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 10:50, 21 April 2015 (UTC)

## Template:Mixbox

I'm creating a draft for various mixbox sub-templates, which can substitute the equivalent chembox sub-templates. Since I'm adding new fields, how do we decide in what order they (fields) are to be listed in? I'm currently working on template:Mixbox Identifiers. Plasmic Physics (talk) 01:00, 27 April 2015 (UTC)

Mix? What mix? Are you suddenly into music or snacks (but then why post it here?).
Anyways, what is the proposed content of this template? I think that is an important question to answer before we define what we .. need to identify there. And then, do we actually want a box for that (if my presumption that you are actually talking about a mixturebox template, then my answer is likely: "I oppose creating a template for that"). --Dirk Beetstra T C 21:47, 27 April 2015 (UTC)
Yes, a mixture infobox. It seems that you're a bit late to the party, so to speak. See the above section under Tin indium oxide. I've decided to create a drafts for consideration. The mixbox is going to contain information about heterogeneous and homogenous mixtures, when the mixture contains a solid, the mixbox will only pertain to the circumstantial, elected phase composition, such as the range of α+β in a hypothetical system. Furthermore, the mixbox will show properties and other data only for special compositions, such as eutectic melting point, eutectoid mp. azeotropic bp., etc. The mixbox has another goal, inspite of major overlap in some of the mixbox fields, it use implementation will ensure that fields which pertain solely to pure substances will not be mistakenly filled for the mixtures, as happened to Hydrochloric acid in the past. Plasmic Physics (talk) 02:51, 28 April 2015 (UTC)
If you end up creating this, would you be able to put in safety data parameters? NIOSH has IDLH, LC50, LD50, PEL, and REL values for a pretty decent number of industrial chemical mixtures and it'd be nice to have a slot for these in this infobox as well as the regular chembox. Thank you! Emily Temple-Wood (NIOSH) (talk) 04:17, 28 April 2015 (UTC)
Noted, I'll add these fields to the draft. Plasmic Physics (talk) 08:29, 28 April 2015 (UTC)
Ah, I see I missed that discussion, I've been out. So, someone asked about a chembox for a mixture, someone answered that mixtures do not go into chemboxes and then a bilateral discussion started regarding whether this could be caught in a template. There is no discussion whether the template should be there in the first place.
By the way, Hydrochloric acid is not a mixture, ITO is. --Dirk Beetstra T C 05:01, 28 April 2015 (UTC)
Solutions are classed as mixtures. If you're still in doubt, the article on the acid even uses the exact word "mixture" to describe it under the section Physical properties. Plasmic Physics (talk) 08:29, 28 April 2015 (UTC)
Solutions are not classed as mixtures. I argue again, hydrochloric acid is not a mixture (and using Wikipedia as a reliable source for that is a nono .. solutions are not mixtures). However, you obtain the solution by mixing two compounds. Moreover, you misread "Hydrochloric acid as the binary (two-component) mixture of HCl and H2O has a constant-boiling azeotrope at 20.2% HCl and 108.6 °C (227 °F)." .. that is talking about the gas phase, not about the liquid (which at best one might consider to describe as a mixture of solvated Cl- ions, solvated H+-ions solvated water molecules and maybe the occasional solvated HCl molecules, but not as a mixture of H2O and HCl), and the gas phase is (indeed) a mixture of HCl molecules and H2O molecules.
I would consider a solution a mixture (and I think that is what IUPAC does) if one in principle could take out the individual constituents, in other words, some solutions behave as mixtures (hexane in benzene, where the molecules do not physically change each other beyond Van der Waals interactions), some solutions are not mixtures (HCl in H2O, where the molecules in the system are not the components the solution was made off), and some mixtures are not solutions (sand and sugar). I get the feeling that that is also what IUPAC gold book suggests in their terminology (they certainly do not talk about mixtures in their definition of solution, or about solutions in their definitions of mixtures), so even the disctinction I made here may be far beyond what IUPAC describes as mixtures and as solutions.
Anyways, I still do not see why we need a mixture box, where the articles about (true) mixtures can describe them and link to the individual components, whereas for solutions a chembox can be more than appropriate to describe a typical concentration (and the rest of the article can describe other 'notable concentrations', and some 'standard concentrations' (1,5, 10, 20, 30% .. )). --Dirk Beetstra T C 13:12, 28 April 2015 (UTC)
H
2
O
| [H
3
O
]Cl + H
2
O
+ δ HCl | δ [H
3
O
]Cl + H
2
O
+ HCl | HCl - this is called the H
2
O
/HCl system, The second boundary is equivalent to the solubility of hydrogen chloride in water. I did not say that all mixtures are solutions, but instead that all solutions are mixtures. Plasmic Physics (talk) 13:19, 28 April 2015 (UTC)
Can you produce me some reliable sources stating that all solutions are mixtures? Again, IUPAC GoldBook does not use the word 'mixture' in their description of a solution, nor does their description of a mixture mention solution. And I still disagree that hydrochloric acid should be treated as a mixture (a mixture of what and what?). --Dirk Beetstra T C 15:53, 28 April 2015 (UTC)
Will the Oxford Dictionary of Science work for you? Heuristically Water and hydrogen chloride is just fine, they exist at the extremes, and all other species present in the system at any one time are in chemical equilibrium with them. Plasmic Physics (talk) 22:43, 28 April 2015 (UTC)
Over IUPAC .. mwaahg. Can I have a linky to that entry in the Oxford Dictionary? --Dirk Beetstra T C 03:59, 30 April 2015 (UTC)
Sorry, it's a paperback. If you're still interested, it is the fourth edition. Good libraries, such as those found at universities should have a copy or two, albeit of the more recent editions. It's good reading, I've read it cover to cover twice. Plasmic Physics (talk) 05:12, 30 April 2015 (UTC)
I still insist that I trust an organisation like IUPAC more to give the definitions than, even, the Oxford dictionary. --Dirk Beetstra T C 17:39, 30 April 2015 (UTC)
What's the proposed scope here? I get the feeling that its all mixtures, including things like aqueous solutions of common compounds (salt, hypochlorite etc), various liquid/liquid mixtures (EtOH/water) as well as alloys and ceramics etc. --Project Osprey (talk) 08:53, 28 April 2015 (UTC)
That is correct. Just so that I'm clear, I'm not going to create articles on mixtures, just to use this template to death. Plasmic Physics (talk) 13:10, 28 April 2015 (UTC)
In what circumstances do you envisage it being used then? Is this a replacement or an alternative to Chembox? Or would you have both on the same page? --Project Osprey (talk) 13:24, 28 April 2015 (UTC)
In exactly those circumstances which you listed. It is not entirely a replacement of the Chembox, since it uses the Chembox; what it is, is a selection of alternative sections which are more suitable than the standard Chembox sections. Thus it is a case of either/or - both will not be displayed, concurrently in the same article. Plasmic Physics (talk) 13:50, 28 April 2015 (UTC)
I'm sorry, I don't entirely follow. You say that it uses the Chembox; does that mean that this is actually a new subtemplate for Chembox? i.e in the same way that Chembox is comprised of {{Chembox Identifiers}}, {{Chembox Properties}}, {{Chembox Structure}} etc this would be {{Chembox mixtures}}? --Project Osprey (talk) 16:12, 28 April 2015 (UTC)
Huh .. a {{Chembox mixtures}}-subtemplate which then would reproduce identifiers, hazards, properties, structures .. and so the main Chembox would only contain this subtemplate. This does not make any sense. I presume that it is the other way around, that this is a new chembox, '{{Mixturebox}}' which contains {{Mixturebox identifiers}}, {{Mixturebox Properties}}, {{Mixturebox Structure}} etc. prepared for having mixtures of different composition in it. As for, e.g., hydrochloric acid, the possibilities go infinite in concentration-choice between 0 and 37% (excluding fuming varieties) I wonder how this will ever be a readable solution either - until now, I think that this is better solved with in-text prose and tables as is currently done. --Dirk Beetstra T C 16:29, 28 April 2015 (UTC)
Precisely! The new templates will be used in the Chembox under names such as {{Mixbox Identifiers}}, etc. With regard to HCl(aq), its Chembox will only display composition specific data at 20.2%, and at the four eutectic compositions. Plasmic Physics (talk) 22:43, 28 April 2015 (UTC)
Only? That is 5 datapoints. And although systematic, the randomness of these datapoints makes distinguishing trends difficult (so one would consider to add 1M, 5%, 10%, 15% to it .. and drown in the table. I argue again, this is better represented in tables in the prose. --Dirk Beetstra T C 03:58, 30 April 2015 (UTC)
Yes, but 5 useful data points nonetheless, where the solution exhibits very particular behaviour. As with the Chembox proper, it is not the intention of the mixbox to show trends. Trends can indeed be represented in the main prose, if they are actually desired. Plasmic Physics (talk) 05:12, 30 April 2015 (UTC)
If this goes ahead, this systematic method of choosing data points is really the only practical option. Consider what happens as the number of constituents are more than two. If the mixbox is to show a trend like you're proposing, then the number of required data points would increase exponentially (figuratively speaking) with each extra constituent. Plasmic Physics (talk) 05:41, 30 April 2015 (UTC)

──────────────────────────────────────────────────────────────────────────────────────────────────── I agree with Beetstra that phase diagrams don't belong in the Chembox - they've often very complex (particularly for alloys) and need to be explained. However, I do see a case where you might like to provide some information on how something behaves as a mixture without having to write a whole section about it (which might not fit the tone of the rest of the article). In the simplest sense that might involve creating some new parameters for {{Chembox Properties}} such as Eutectic point and Azeotrope --Project Osprey (talk) 09:37, 30 April 2015 (UTC)

Does that mean by extension that you agree with me too, because I am also opposed to having entire phase diagrams in the Chembox?. I'm drafting exactly what you're proposing, albeit in a dedicated sub-template to avoid confusion by novice editors, who will no doubt try and fill (incorrectly) non-applicable or otherwise inappropriate fields. Plasmic Physics (talk) 10:23, 30 April 2015 (UTC)
I also suggest that we limit the composition range to the isothermal phasic structure in which the most common formulation is located. For example, if at STP a mixture with the common formulation A:B has the phasic structure of α+β, then the compositional range of the Chembox is limited to the α/α+β and α+β/β boundaries. Also limit the temperature in a similar manner, take only the temperature range about RT, for which there are one to one transitions within the afore limited compositional range. Accordingly, the Hydrochloric acid Chembox will only cover the liquid solution, not the solid, vapour, or liquid and vapour portions, and will only cover 0-68% wt, if that is its solubility. I see one problem having arisen, what to do about miscibility gaps? Do we split the composition range in two, or do we ignore the gap entirely in terms of the range? I'm in favour of the latter, for the sake of continuity. Or, is there a third option not yet considered? Plasmic Physics (talk) 11:04, 30 April 2015 (UTC)
For what its worth, and I am sorry to have to say this - I have rarely seen anything done by Plasmic Physics that is good good for Wikipedia. He may have good intentions, but he is possessed by frantic instincts and strange or weak technical perspectives. IMHO, almost every article he touches is worse for his contributions. --Smokefoot (talk) 12:05, 30 April 2015 (UTC)
You're are most certainly not sorry, as this is an absolutely unnecessary criticism of my character. You've been warned before by others for laying into me for no good reason. I strongly suggest you stop before you take this somewhere we both don't want to go. Plasmic Physics (talk) 12:33, 30 April 2015 (UTC)
Not only unnecessary, but unacceptable. WP:NPA refers. Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 15:44, 30 April 2015 (UTC)

Look, there is nothing wrong with PP making the templates and see what comes out of this. I do however expect that PP regularly consults the community (like this question here) , including how this actually is going to be (maybe not as a replacement of the chembox (more boxes is less recognisability) but as a systematic box further down the page. I also suggest to apply the condition that before anything goes life in mainspace, it is first properly put into sandboxes in user or project space and discussed to death, and we get a clear 'go' by consensus (clear support to get it implemented in mainspace, not a situation where there is no one commenting and hence no opposition). --Dirk Beetstra T C 17:39, 30 April 2015 (UTC)

Agreed. I'm having a hard time picturing what this is going to look like; you say you don't want to include phase diagrams but then go on to talk about listing α+β, then α/α+β and α+β/β boundaries - which sounds very much like a phase diagram to me. Is there any way you could do a mock-up of it so we could see that it would look like? I feel I should point-out that PP can't actually edit Chembox. Partly because he's already banned from doing so, but also because its protected so that only template editors and administrators can edit it. We would at some-point have to move this conversation over to Wikipedia talk:Chemical infobox and see what DePiep makes of it. --Project Osprey (talk) 22:32, 30 April 2015 (UTC)
No, no, I didn't mean that the boundaries are to be expressed in detail, but only that they be used to limit the scope of the infobox. I'm not actually banned from editing the master chembox, only the field entries in articles which use it. Plasmic Physics (talk) 10:18, 1 May 2015 (UTC)
For what it's worth, I was planning on discussing it once the first drafts were completed, but it seems that I've been preempted. And for all that has been said, I still lack an answer to my original question. Plasmic Physics (talk) 22:20, 30 April 2015 (UTC)
Your first question was " Since I'm adding new fields, how do we decide in what order they (fields) are to be listed in? I'm currently working on template:Mixbox Identifiers" - its really hard to answer without knowing which fields we are talking about. Do you btw. have a link to the template? {{Mixbox Identifiers}} doesnt exist. Christian75 (talk) 23:12, 30 April 2015 (UTC)
So you're saying that there is no general method, that each new field is added in a particular position on a whim? So far, I'm going to add USN number to the identifiers mixbox, while removing others. It's in my sandbox, it has not come very far. Plasmic Physics (talk) 23:39, 30 April 2015 (UTC)
The identifiers are alphabetical order, and other fields in other "properties" are what the template editor thought was a good idea. Sometimes "the most important" are first ... Christian75 (talk) 08:59, 1 May 2015 (UTC)
Thanks. What is the purpose of the CASNos, CASNoOther, and CASOther fields? Is anyone aware that the EINECS field entry is a dead link? Plasmic Physics (talk) 10:10, 1 May 2015 (UTC)
If I don't get an answer from someone, I'm going to assume by default that they are unnecessary, and consequently remove them from the draft. Plasmic Physics (talk) 05:47, 4 May 2015 (UTC)
The identifiers are currently in alphabetical order (if the edit has not been undone), but there it seems there was no consensus for the bold implementation of that
CASNos, CASNoOther and CASOther are I think all obsolete now (replaced with multiple CASNo#-fields; it may be that one is left over for hand-formatting and addition of more in extreme cases), EINECS is of interest, though maybe the link needs to be adapted. --Dirk Beetstra T C 06:54, 4 May 2015 (UTC)
Thanks. Plasmic Physics (talk) 07:20, 4 May 2015 (UTC)
If the Mixbox call up a template, how do I add the template directly? For example, the Chembox calls up:
{{#if:{{{UNII|}}} |{{Chembox UNII |value={{{UNII|}}} }}}}
How would I add {{Chembox UNII}} directly into the chembox, rather than create a dedicated article? Plasmic Physics (talk) 09:35, 4 May 2015 (UTC)
Just use as normally: {{Chembox UNII|{{{UNII}}}}} - but then it shows up when there is no UNII parameter given. --Dirk Beetstra T C 10:32, 4 May 2015 (UTC)
I see, so would need a dedicated template for it to only show when the value is not empty. Plasmic Physics (talk) 10:37, 4 May 2015 (UTC)
You could also do {{#if:{{{UNII|}}}}|<what to display including {{{UNII}}}>}}, then all between '|' and the final '}}' will be displayed only if there is something in the parameter 'UNII'. You will however find that on more complicated templates that quickly turns into a form of spaghetti that is very difficult to read (especially if the 'what to display' becomes multiple lines). Keeping a line for each, with a short statement and calling a subtemplate keeps it more clear. Also to keep the subtemplates in line with each other is easier, and depending on the sensitivity of the subtemplates ('Chembox UNII' in this case), you can leave some free to edit, others to template editors, and yet others to admins only (the calling template ('Chembox Identifiers') generally gets a high protection level due to the damage a single edit (by any editor, or a vandal) can do to many pages). --Dirk Beetstra T C 11:02, 4 May 2015 (UTC)

## The Merck Index Online

Quick straw poll: how many of you have access to The Merck Index Online (perhaps though work or academic institution)? Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 15:24, 27 April 2015 (UTC)

I do, do you need something in particular? Emily Temple-Wood (NIOSH) (talk) 22:43, 27 April 2015 (UTC)