Wikipedia talk:WikiProject Chemistry/Archive 48

Aminobenzal
Is this correct and notable? Ketal formed using 4-dimethylaminobenzylidene? BTW it seems that this name is applicable to only one drug. Similar with e.g. Cyclopentanonide, Pentanonide. Acetophenide and Acroleinide seems a bit more popular, but still... I came across it on Wikidata. Wostr (talk) 18:25, 18 June 2019 (UTC)
 * I think the meaning given in the article is a drug-term (a shortened form of a piece of a systematic name), just like the other two words in "Triamcinolone aminobenzal benzamidoisobutyrate". This should probably be merged into Benzylidene acetal, as a specific and novel example of class. DMacks (talk) 14:33, 19 June 2019 (UTC)
 * Agreed. I looked up crystal structures with N-C6H4C(H)(OC)2 skeletons in the Cambridge Xray database, thinking that maybe the 4-dimethylaminobenzylidene might be common.  About 10 structures, and most are nitro derivatives (O2N-C6H4C(H)(OC)2), not anilines. --Smokefoot (talk) 14:46, 19 June 2019 (UTC)

Expert help is needed at Gel point
You are invited to join the discussion at Gel point. Shhhnotsoloud (talk) 11:26, 22 June 2019 (UTC)

Saturated and unsaturated compounds vs Saturation (chemistry)
We probably should resolve these two articles so that the distinction is a little more crisp.

One scenario: --Smokefoot (talk) 13:44, 1 July 2019 (UTC)
 * Saturated is a disambiguation page. The adjective is widely used (saturated solution, etc)
 * Saturated and unsaturated compounds to inherit most of the content in Saturated. It will become highly chemically oriented.

C15H25N3O
Hello. I am from the New Pages Patrol. Someone created this page: C15H25N3O into an index page for Caproxamine and Lisdexamfetamine. I have no idea if this is accurate. Can someone from this project or the daughter projects verify the accuracy of this page. Your help is much appreciated. Regards ---Steve Quinn (talk) 04:45, 7 July 2019 (UTC)
 * the Infobox for each of those pages lists "C15H25N3O" in the "Formula" field. I also checked the structure-diagrams (the line-image) in each infobox and found that they match as well. DMacks (talk) 05:55, 7 July 2019 (UTC)
 * OK. I didn't notice the infoboxes. Thanks for looking into this. ---Steve Quinn (talk) 05:59, 7 July 2019 (UTC)
 * No worries. Thanks for NPPing and thinking to ask in a relevant active place! DMacks (talk) 06:03, 7 July 2019 (UTC)

Polymer
There is a group of polymer chemists from IUPAC who want to work on bringing the Polymer article to FA. Hopefully there will be some serious work done on that article soon, but some guidance from here would be very useful and welcome. Thanks, Walkerma (talk) 10:14, 10 July 2019 (UTC)
 * That's good to hear. It's an important article that could definitely use some improvement.  Since this project is much more active than WikiProject Polymers, I would encourage them to bring any questions or concerns here.  They should get more prompt responses here and the regulars are friendly and helpful.  -- Ed (Edgar181) 12:19, 10 July 2019 (UTC)
 * The polymer area is so big and in a way so mature, that most of the referencing should/could be achieved by reference to textbooks and encyclopedia, per WP:TERTIARY. Good luck.--Smokefoot (talk) 19:35, 10 July 2019 (UTC)
 * Why not aim for GA first? -DePiep (talk) 19:42, 10 July 2019 (UTC)
 * Some missing sections would be on history, use, and biologic function. But the article has to have a suitable level of detail, so that some content may have to go into the sub/related articles. Overall there should probably be 2 to 4 times as many references. Another step is peer review prior to a FA. Graeme Bartlett (talk) 06:09, 11 July 2019 (UTC)
 * Thanks for the feedback, this is all helpful advice. I'd certainly support the idea of GA first.  Thanks, Walkerma (talk) 03:36, 16 July 2019 (UTC)

WikiProject Chemistry/Article alerts update
As a heads up, the alerts will now report proposals for mergers and splits, as well as AFC submissions. There's a bit of a backlog, but now you have a way to track it! &#32; Headbomb {t · c · p · b} 02:08, 31 July 2019 (UTC)

Some orphaned chemistry articles
Hello, I've been trawling through the orphaned articles categories and found a couple I could use help with: thioselenide and purinones. Are these important enough subjects to require standalone articles? If not, could they be merged, somewhere? Or is deletion in order? I can do any necessary legwork, I just need to be steered the right way by people who know what they're talking about (ie, not me). &spades;PMC&spades; (talk) 13:17, 2 August 2019 (UTC)
 * I added a bit of referenced content to thioselenide, enough to suggest it shouldn't be deleted, but perhaps it can be merged somewhere. -- Ed (Edgar181) 15:19, 2 August 2019 (UTC)
 * Ooh, and you de-orphaned it, brilliant, thank you :) &spades;PMC&spades; (talk) 22:20, 2 August 2019 (UTC)

Science project
I just happened across the article Science project, which looks rather unloved. Expansion would be welcome and probably not that difficult. XOR&#39;easter (talk) 01:49, 14 August 2019 (UTC)

&#123;{Sidebar periodic table}}
Can anybody look at this new concept for the sidebar? It provides hints for notation of groups and periods which may look cryptic for some people. Incnis Mrsi (talk) 18:10, 11 August 2019 (UTC)
 * I don't understand the question. There are no recent "new" things. "Hints"? (I pinged WT:ELEMENTS). -DePiep (talk) 20:53, 11 August 2019 (UTC)
 * No recent "new" things, Yes, it perhaps is more topical for WP:WikiProject Elements than here,  unfortunately forgot about it. Incnis Mrsi (talk) 21:10, 11 August 2019 (UTC)
 * Sandbox proposals, then. Please propose changes properly. -DePiep (talk) 21:18, 11 August 2019 (UTC)
 * Comparing the latest versions of the template and its sandbox (special:diff/896356272/910384468), the only differences I see are the addition of, which doesn't seem to have any impact that I can see. Unless there is a specific reason for adding that stuff, I'd prefer to stay with the current one. But perhaps someone can enlighten me as to what benefit the provides. Perhaps I'm missing something really obvious. YBG (talk) 22:50, 11 August 2019 (UTC)

I don't understand the request. Under "By periodic table structure" I can see three headings: Groups (1--18); Periods (1--7, …); and Blocks (s, p, d, f, …). So, I guess the PT can be structured by Groups, Periods, and Blocks. And if I want to know more I can click on a w/link. For an info, this looks OK to me.

The sandbox changes look OK to me. They add little fly-out boxes to each of the w/links. Sandbh (talk) 03:05, 12 August 2019 (UTC)
 * Yeah, I like those extra boxes that appear when you hover over the links. Double sharp (talk) 03:41, 12 August 2019 (UTC)
 * Here is the . -DePiep (talk) 13:25, 13 August 2019 (UTC)

Will anybody help to characterize the group 3? Or any idea to make s less verbose? To some extent we should conserve the end user’s bandwidth yet. Incnis Mrsi (talk) 06:37, 12 August 2019 (UTC)
 * OK, now I see the difference. My general impression is that it is trying to cram too much info into an navbox and presenting that info in what seems to me to be an unexpected way that seems to come close to an WP:EASTEREGG. But this is not a hill I'd die on. If the consensus determines that what appears to me to be unnecessary clutter, then let's change the period titles, for example, from ' to the more quickly readable ' or something similar. YBG (talk) 07:57, 12 August 2019 (UTC)
 * And just a random thought: suddenly disliked [my own] “Li–Ne” as the dash may be taken for a symbol of covalent bond. Going to replace it with “Li … Ne”. Incnis Mrsi (talk) 10:18, 12 August 2019 (UTC)


 * Also Periodic table has essentially the same section. In absence of objections ’ll deploy the changes to both navboxes soon after resolution of the crisis with Group 1. Incnis Mrsi (talk) 10:25, 13 August 2019 (UTC)
 * Now I get it. The changes use the &lt;span>  attribute a span to describe the topic (wheareas otherwise we would see the target article title). The title appears as a box, also knows as "tooltip box". As it happens, when hovering over with the mouse, my settings also show a preview of the article lede section (don't know the gadget name, sorry).
 * As YBG writes, it is cramming extra info in there (while still not being complete eg re the elements list of a period). Unlike YBG, I am not convinced yet. I think this is a slight misuse of the title attribute, and therefor not recommended HTML-wise. However, I cannot find the documentation on this. (Unfortunately, we have used this gimmmick a long time, eg here; I'm not sure about that one too).
 * So I'd prefer this usage be researched first (ask WP:VPT?). -DePiep (talk) 13:43, 13 August 2019 (UTC)
 * If  is used in abbr which is transcluded to thousands articles, then what’s the merit to discuss its use in navboxes specifically? Incnis Mrsi (talk) 16:56, 15 August 2019 (UTC)
 * From abbr: "The template Abbr is used to write an abbreviation with its meaning. It is a wrapper for the HTML element &lt;abbr>...&lt;/abbr>, the element used by most web browsers to create a tooltip indicating the meaning of an abbreviation or acronym."
 * So: the http element &lt;abbr> is not &lt;span>, and so is not its title attribute definition. So the abbr reference is inappropriate.
 * Now both title attributed do signify a true title (for example, showing the title of an article in regular wikilink hovering). But in no way a title should be confused with a description, as the current sandbox proposal does.
 * On top of this all: the template mentions (in top) a link re deprecation: Redirects_for_discussion/Log/2018_May_9. I think this RfD clearly prohibits "tooltip" text other than abbreviations. -DePiep (talk) 17:37, 15 August 2019 (UTC)
 * The discussion cited WP:Manual_of_Style/Accessibility which advises against such things… in articles. It was silly not to consult MoS beforehand, but now asked for clarifications about navboxes. Incnis Mrsi (talk) 20:05, 15 August 2019 (UTC)

SME needed for Draft:Inorganic carbodiimides
Could somebody please review Draft:Inorganic carbodiimides. Thanks. -- RoySmith (talk) 23:52, 19 August 2019 (UTC)

Request for input regarding Merge Request
There is a request for the merger of the article into  at the Merge Request Noticeboard. Discussion is at an impass. Your input is welcome at the discussion page >>>HERE<<<. Thank you, GenQuest  "Talk to Me" 17:49, 20 August 2019 (UTC)

&lt;chem>: an AI for people having structureless mind
A miraculous AI  achievement: the software is able to determine when the formula reaches a certain "complexity" and switches its syntax rules without warnings. The people of 2010s like AI – it brings equality between right and crooked hands, between the smart and the stupid. Everyone intelligent is susceptible to making the syntax wrong as much as an idiot who can’t tell a hyphen of a colon. Poor old guys like Incnis_Mrsi are confused – they are accustomed to predictable syntax patterns which permit for making localized tweaks without considering complexity of the whole code. Poor Incnis_Mrsi was able to only using suggestions by, who added several phrases to the manual. The phrases are about things not interesting for modern people – really, who may override default typesetting or care about other similarly dull things? It’s the domain of (Microsoft Office)-style AI. What an arrogant prick is this Incnis_Mrsi to imagine he knows how $hν$ should be set in glyphs. And who likes the (Cold War)-era syntax now? This legacy cruft was favored by such people as Dennis Ritchie (C) or Donald Knuth (TeX), but modern developers are cooler than the dinosaurs. Modern developers may master even such languages as PHP which was unlikely possible in the 1970s or so. What for nowadays? Just push your dumb keyboard, username, and don’t try to bring any order into the resulting groups of characters.

Seriously speaking, users who voted this AI punk into WP:MOSCHEM now earn my disgrace. Incnis Mrsi (talk) 10:11, 6 August 2019 (UTC)
 * I am sure that use of and  is deprecated here. undefined has some acceptable features. Graeme Bartlett (talk) 12:07, 6 August 2019 (UTC)
 * Good news. suppose nobody here objects throwing the unsyntax out of the atmosphere of Mars into deep space. Incnis Mrsi (talk) 12:51, 6 August 2019 (UTC)
 * We don't really stake much of a claim on the astronomy pages. --Project Osprey (talk) 13:00, 6 August 2019 (UTC)
 * An example of astronomy topic is atmosphere of Makemake. Atmospheres of Mars and even of Pluto are not astronomy… anymore. Welcome to the Space Age, . Incnis Mrsi (talk) 13:18, 6 August 2019 (UTC)

The thing escalated to Help talk:Displaying a formula where a user edit-wars against me apparently in favor of &lt;chem> (or perhaps mostly for personal reasons, not sure). Incnis Mrsi (talk) 13:46, 10 August 2019 (UTC)

Related: 	Template talk:Chem2‎‎. Incnis Mrsi (talk) 20:02, 16 August 2019 (UTC)

now work for improving chem2 where the original creator left many gotchas and faults. Especially opinions on encoding of prime symbols (or apostrophes, for typewriter fans) are welcome. Incnis Mrsi (talk) 16:07, 27 August 2019 (UTC)

Intermetallic compound
Do we have any naming conventions about intermetallic compounds such as CaPt2, MgCu2, etc.? --Leiem (talk) 17:16, 20 August 2019 (UTC)
 * As far as I know we use the most common name. Sometimes the literature only uses a formula. The title would then be the flattened formula. CaPt2. MgCu2. Then we could use an IUPAC name, but it may be unsourced. I have made up names for some articles I wrote. You could use calcium platinum or ?? Calcium diplatinide?? ... Let me see if that's a thing! Graeme Bartlett (talk) 07:40, 22 August 2019 (UTC)
 * It appears not to be in use, as the term is only used on Wikipedia talk pages. But platinide appears valid. Graeme Bartlett (talk) 07:43, 22 August 2019 (UTC)
 * Dictionary of Inorganic Compounds calls MgCu2 "copper magnesium (2:1)". ChemNerd (talk) 12:24, 22 August 2019 (UTC)
 * The names in SciFinder are "Copper, compd. with magnesium (2:1)", "Magnesium, compd. with copper (1:2) (8CI)" and "Magnesium copper (Cu2Mg)" . --Leiem (talk) 02:22, 23 August 2019 (UTC)

In our article for MgCu2 we give it the IUPAC name of "copper-magnesium (2:1)". I think this comes from an old IUPAC recommendation to name intermetallics in alphabetic order, rather in order of electronegativity. CaPt2 is an intermetallic rather than a platinide. Sandbh (talk) 23:21, 23 August 2019 (UTC)
 * In the Russian Wikipedia, names such as "diplatinumcalcium" are used. Burzuchius (talk) 18:44, 29 August 2019 (UTC)

Chemistry icon
Hi all, during our refresh of MediaWiki icons, the chemistry icon (used in the visual editor to insert formulae) was updated. There is an ongoing discussion on the Phabricator task about whether to used a closed beaker or an open top beaker. If any of you have an opinion, please reply here or on Phabricator. Thanks, ESanders (WMF) (talk) 18:17, 30 August 2019 (UTC)
 * A note here, the icon under discussion - whether open or closed - does NOT represent a Beaker_(glassware), but an Erlenmeyer flask. The gif quoted in the phabricator case(File:More_simple_chemistry_apparatus.gif) calls the "Erlenmeyer flask" a "conical flask".
 * Now unless there is some difference in terminology in other English-speaking countries, I would posit that the very fact that the incorrect terminology is used in the phabricator item indicates either carelessness or a disconnect with the target audience.
 * Using a picture of a Erlenmeyer flask instead of a picture of a beaker is a good idea since it has a more distinctive shape. To make a beaker distinctive, one would have to over-emphasize the "beak" or pouring spout, which I don't think would work out.
 * The statement is made that "When drawing chemical apparatus, the top is left open unless the beaker has a lid". But the question is, why? Is it a matter of convention, esthetics, recognition, or usefulness?  I believe that the reason for this observation is that the pictures referenced in the pbabricator case are intended to be combined with other icons to create a large diagram containing multiple vessels.  If this convention were not followed, a diagram such as the one in File:Anaerobic respiration equipment.png would appear to show fluids flowing through walls.
 * But if I understand correctly, the purpose of this icon is to stand alone, not to be combined with other objects to create a complicated piece of chemical apparatus. That being the case, the need to not show fluids flowing through walls is immaterial; what is paramount is recognition and esthetics.  On that basis, I believe the closed form is more recognizable and esthetically preferred.
 * I would gladly defer my opinion to others who are fluent in chemistry, but I would strongly encourage people to emphasize the opinions of the chemically fluent instead of the opinions of those who do not know the difference between a "beaker" and an 'Erlenmeyer flask". YBG (talk) 20:00, 30 August 2019 (UTC)
 * I responded on phab (executive summary of my thoughts: "'closed outline', but add 'solid filled' as third option"). DMacks (talk) 04:47, 31 August 2019 (UTC)

Diketone vs dicarbonyl: future move?
We have a nice compact article on diketones, encompassing 1,2-, 1,3-, and 1,4-diketones. I am guessing that most chemists would rather consult an article on 1,2-, 1,3-, and 1,4-dicarbonyls, which would include the keto-aldehydes and the dialdehydes. Its a big class of compounds, and one could foresee future splitting into individual articles, such as 1,2-Dicarbonyl (biacetyl, glyoxal being prominent), 1,3-Dicarbonyl (acetylacetone and malondialdehyde being prominent), etc. --Smokefoot (talk) 16:26, 18 August 2019 (UTC)
 * Sounds like a useful re-organization of the material. It could also absorb Keto acid, an article that likewise does not have any unique unifying chemistry except by structural definition. DMacks (talk) 05:37, 19 August 2019 (UTC)
 * As specific unifying themes of position regardless of functional group, then the 1,2 section/article could talk about the general effect of the adjacent C=O (bond length, electrophilicity); the 1,3 section/article about formation by aldol-like addition, enhanced tautomerization, and as metal ligands; etc.. DMacks (talk) 05:52, 19 August 2019 (UTC)
 * Maybe this idea was naive or too ambitious. --Smokefoot (talk) 00:01, 2 September 2019 (UTC)

Adsorption trash
The palladium article [ adsorbs some trash]. The warning was dismissed. Watchers (other than myself) are slow to react. Unfortunately didn’t ever hold a piece of palladium in my hands, hence deem inappropriate to engage in a hardcore edit war over it. Volunteer to undo waste adsorption? If not to intervene timely, superficial adsorption may gradually turn to waste absorption characteristic to poorly maintained Wikipedia articles. Incnis Mrsi (talk) 17:43, 6 September 2019 (UTC)
 * , school-texts (and even reputable undergrad texts) often emphasize that Pd adsorbs Hydrogen (which frankly, is the most important property) and does not go to the extent of discussing further subsurface adsorption i.e. absorption. What's the issue and the corresponding assumption of bad faith? &#x222F; WBG converse 18:00, 6 September 2019 (UTC)
 * Let’s read into Palladium readily adsorbs hydrogen at room temperatures, forming palladium hydride PdHx…
 * then to palladium hydride . What does palladium to form PdH? Isn’t the latter a three-dimensional solid, after all? As for faith, the problem in hand is mostly scientific and better to avoid religious dimension. Incnis Mrsi (talk) 18:44, 6 September 2019 (UTC)

Nomination for deletion of Template:Chem A-Class
Template:Chem A-Class has been nominated for deletion. You are invited to comment on the discussion at the template's entry on the Templates for discussion page. PC78 (talk) 19:29, 7 September 2019 (UTC)

Deletion discussion
The discussion at Articles for deletion/4-Ethylamphetamine had to be extended because additional input is needed. Members of this Wikiproject may be interested in contributing. ChemNerd (talk) 15:15, 24 July 2019 (UTC)
 * I agree with this deletion and the need for additional input. Hayleysmitty18 (talk) 02:29, 12 September 2019 (UTC)

Organic Syntheses refs
Background: We can probably agree that Organic Syntheses is a nearly ideal source, being WP:SECONDARY and open-source.

Lately I have been converting citations in the OrgSyn template Template:OrgSynth to the generic journal template. Upon reflection maybe I should just stick with the Template:OrgSynth.

Here is the situation. OS publishes annual volumes. Presently these volumes are exclusively on-line. But at one time they were actual booklets. Every 15 years or so, the individual volumes would be organized into a collected volume, with new pagination and new publication year. The scholarly information (date of original work, the official journal record) is in the individual volumes, not in the collected volumes. Many of our Template:OrgSynth citations only include info on the collected volume. That material should probably be voided and replaced with the actual volume.--Smokefoot (talk) 09:22, 14 September 2019 (UTC)

Chemical formula pages
I wrote an anon bot that gathers a few data from chemical infoboxes including chemical formulas. (Here is the list of formulas and articles.)

Now I am checking formula pages in enwiki and correct them manually. 80% of formula pages are redirs to compounds and over 3000 such redirs are missing. The list is on my user page.

I want to create them with a bot and am asking for your approval to mass-creating. Gyimhu (talk) 10:04, 7 August 2019 (UTC)
 * I like the principle.
 * So "formula page" is like [[C100H132N26O13 ]] and you want to create these, as a redirect? Is this a common rewriting in chemistry? What if the formula is not just empirical (symbols & number-of-atoms only), but has structural info like -brackets?
 * It could be helpful to check formula on a infobox with the formula on wikidata. A difference might indicate an error. -DePiep (talk) 10:12, 7 August 2019 (UTC)
 * Many isomers of C6H16Si may exist, not necessarily triethylsilane. Moreover, redirects are cheap, but not exactly costless. Does Wikipedia really need this burden in redirects to thousands compounds? Incnis Mrsi (talk) 10:16, 7 August 2019 (UTC)


 * these redirects are not useful. However for the simpler inorganic compounds the formula redirect will be useful, as it is quite likely to determine the compound and article. For most of the multicarbon organics there are many known isomers and so the page should be a disambiguation or set index, even if many of the possibilities are not notable at this point in history. Graeme Bartlett (talk) 13:29, 7 August 2019 (UTC)
 * Welcome to chemistry, . --Smokefoot (talk) 22:34, 7 August 2019 (UTC)
 * Special:Search seems to do a good job of finding articles by chemical formula as long as the infobox itself does not both manually override the default Hill order of the chemical formula and also omit the InChI. And it does so with zero maintenance (neither creating a redir not converting a redir to a DAB). DMacks (talk) 05:34, 8 August 2019 (UTC)
 * There's possible (probable) overlap with Category:Dictionary_of_chemical_formulas. I'm indifferent to this idea, I never search by formula myself but I'm sure there there are those that do, or would wish to without having to resort to Special:Search. Would some sort of complexity cut-off be necessary? - I can't imagine anyone actually searching for C100H132N26O13. --Project Osprey (talk) 10:43, 8 August 2019 (UTC)


 * Chemical formula consists of atoms and number of atoms. All characters are alphanumeric. Organic compounds begin with C continued with H, the rests are in abc order. E.g. isomer page of formula C6H2(NO2)3CH3 will be C7H5N3O6.


 * I think this pages are more useful for organic compounds. The formula page contains isomers. If only one compound exists with a formula then the page is redir to the compound. 80% of formulas are uniq (redirs). I create/update the (not redir) isomer pages manually so it is an other case.


 * The isomer page is not my idea. My experience is that ⅔ of organic (more exactly: C-containing) compounds have correct isomer pages. There is ~18000 compound articles in enwiki, C is in ~15000, and in ~1400 my bot didn't find formula because they are polimers, more then one compounds in Formula field of infobox, or my bot didn't recognise formula because of crystallic water, more given formulas, isotope in it and there are few other reasons. Gyimhu (talk) 16:53, 9 August 2019 (UTC)
 * What the user is speaking about and why s/he pings me? Again, for most of the multicarbon organics there are many known isomers – it is about a scientific fact, not the user’s idea. Which namely of isomers should have (or are expected to have) distinct articles in en.Wikipedia is not a question solvable by a bot. Incnis Mrsi (talk) 17:15, 9 August 2019 (UTC)
 * He. Sorry for ping. I came recently from Hungarian wiki and there it is custom.


 * I wrote a bot that gathers chemical formulas from articles, order them and make them searchable. If there is only one compound with a formula then it is possible to create redir article by a bot. This is only a technical problem. Isomer pages with more then one compounds are different because they are used as disambiguation pages in enwiki and contain not only formulas but other information too. Gyimhu (talk) 17:28, 9 August 2019 (UTC)

To user:DePiep: I tried to compare formulas in wikidata, enwiki and huwiki. Wikidata is hopeless: full of errors. There are many compunds where there are quite other compounds in content and article name. I corrected a few then gave up.

Yes, nobody will search for C100... but the most formulas have only 10-20-30 carbons.

InChi is a good idea and I have plans with it and with SMILES. Gyimhu (talk) 17:40, 9 August 2019 (UTC)
 * My point with InChI is that by defintion it already always includes the exact formula in its first layer. So it's guaranteed that the formula will be findable by searching. And I re-iterate my serious concern about keeping this up-to-date. I think it's worse that we have a formula page that does not link all existing articles than to have no formula page at all. It substantially hides what we actually do have as new pages are created (bias towards older compounds), rather than having them all automatically and equally visible.
 * If I understand your last sentence, you have a longer-term plan to create redirects for InChI and SMILES strings? I strongly oppose. Nobody wikilinks to specific compounds that way and again they are all already and automatically visible to searching both using the wiki search-engine and google itself. We tested that extensively when developing the hideable fields of chembox and during several validation and bot-monitoring projects. DMacks (talk) 17:56, 9 August 2019 (UTC)
 * DMacks, in my experience a search using the molecular formula of a certain chemical compound will not always result in finding the page for that chemical, even when that page includes both the molecular formula and the InChI in the infobox. Taking a random example, if I put C19H22F2N4O3 in Wikipedia's search box, the results don't include sparfloxacin. -- Ed (Edgar181) 18:15, 9 August 2019 (UTC)
 * If I put it in quotes, that article was the only hit (which also means it's somewhere in the list when not quoted, though I'm not going to page through 52K hits to find it). As an alternative, I tried limiting the search to subcats of top-level chemistry and drug cats, but the number and depth of categorization overflowed Mediawiki's little brain. DMacks (talk) 05:29, 10 August 2019 (UTC)
 * Don't worry, I'm not that dangerous. :) My plans are for my homepage. First I want to write a program that compares chemical formulas with InChi and SMILES and list articles where they are missing. The results can be uploaded to a wiki page in my homepage or to an enWiki user page as you wish.
 * Don't worry, I'm not that dangerous. :) My plans are for my homepage. First I want to write a program that compares chemical formulas with InChi and SMILES and list articles where they are missing. The results can be uploaded to a wiki page in my homepage or to an enWiki user page as you wish.


 * There were several thousands of formula pages (including redirs) when I started correcting them. The set of chemical articles is a special form database. I have been database admin for 20 years: I know that a database is either complete in some respects or not worth much. At least as bad are the wrong data. The database already exists: the best we can do to fix it I think. Later the maintenance is possible using a bot: it can list the changes in articles. Subsequent manual maintenance is no longer a big task.


 * After creating the redirs I find necessary another manual check where the bot checking fails. My bot is already monitoring the changes: the only thing to do is formatting the output. This is the next step.


 * A have created ~1000 redirs manually. This is a boring and time consuming task. Gyimhu (talk) 20:31, 11 August 2019 (UTC)


 * The remarks by DMacks re InChI and searching are worth more consideration. It might give us a guideline on maintaining and curing and . -DePiep (talk) 10:38, 14 September 2019 (UTC)

Chemical Abstracts and PubChem as sources?
Question: Chemical Abstracts and PubChem provide a great deal of data on chemical compounds. Are these reliable sources? Should they be cited? Suggested answers: --Smokefoot (talk) 21:10, 29 September 2019 (UTC)
 * In general: no, but the sources that they cite might be (although WP:SECONDARY and WP:TERTIARY are preferrable when possible).
 * We should accept their data to populate ChemBoxes with information on physical properties and structural/safety descriptors
 * PubChem is a reliable source of names.
 * About PubChem, I think only the PubChem generated IDs (SMILES, InChI, InChIKey) can be reused. The names should be avoided as many people don't distinguish between stereoisomers. And PubChem generated IDs are not primary sources: PubChem team uses a tool to generate those IDs. Snipre (talk) 12:11, 1 October 2019 (UTC)
 * For molar mass calculations, I cannot trust PubChem. PubChem uses standard atomic weight values different from the formal (CIAAW) ones; some of these are stated in WD as std atomic weight (Ca, ). -DePiep (talk) 12:20, 1 October 2019 (UTC)


 * The generated IDs are derived by processing of other structural data, so as long as we trust that they actually have the correct structure, I trust their implementation of a purely mechanical algorithm based on it. For example, by definition, everyone who generates InChI from the same structure would get the same result because InChI is literally derived exactly on the structure. MW is based on the formula, but depends as DePiep notes on their atomic weights. We don't need to do that at all because our infobox can do the MW calculation locally and we can make sure we're using whatever atomic weights are consensus for our site. It's true that stereochemical detail is sometimes omitted on PubChem, but I think it's also true that a non-stereospecific name is 1) useful and 2) just missing stereoisomeric detail (adding those details would not alter the constitutional-isomeric name aspect). For physical properties, I see it as a secondary/teriary that is usable depending on what source they cite for it. But in all cases, need to check for hydration and salt forms (PubChem sometimes does funny things with conjugate bases of acidic compounds). DMacks (talk) 12:30, 1 October 2019 (UTC)


 * For PubChem I have found numerous errors. Structures and names can be wrong. There may be extra CAS numbers or EC numbers that actually belong to related substances. However SMILES and InChi do match the structure they have, and so will be right if that is right. When I contacted the staff they were not interested in fixing anything and blamed the contributors, which for some entries you can see where the info came from. Mostly the information is correct, but it is good to have a sanity check and compare it to other databases/sources. Also don't count on PubChem for proving notability. I do use PubChem to populate safety information, but this too is an aggregation and so may have a lot more codes than you would find on the average container for the product. Safety will also depend on how much you are dealing with, there is a difference between 1 g and 1 ton. I am also adding PubChem CIDs to those pages missing them, and adding any other ids that PubChem has (RTECS DSTXID chebi chembl unnumber unii) For Chemical Abstracts, isn't that authoritative for CASNo?Graeme Bartlett (talk) 12:35, 1 October 2019 (UTC)
 * Definitely a GIGO database. Their structure diagrams are sometimes laughable nonsense too—correct connectivity, but impossible 3D forms. DMacks (talk) 13:14, 1 October 2019 (UTC)

Who has access to Food Chemistry?
claims there's a copyvio from Food Chemistry (an Elsevier journal) in Menengic coffee. Unfortunately, I only have access to the abstract, so can't verify the copyvio. Anybody have a subscription and can check this out for me? -- RoySmith (talk) 19:27, 8 October 2019 (UTC)
 * , I see that the copyvio has now been redacted by another admin. All the text was a direct copy-paste from the paper. If you'd like to see it, I found a free-to-read author's copy on ResearchGate: . PS, in case you didn't know already, you can get free access to many academic sources with your Wikipedia account through The Wikipedia Library. In a pinch, you can also try Sci Hub. Hope that helps... --IamNotU (talk) 03:18, 9 October 2019 (UTC)
 * Yeah I saw. That's fine.  I do have access to JSTOR via TWL, but this wasn't available from them.  I just put myself on the waitlist for Elsevier ScienceDirect; thanks for the suggestion.  -- RoySmith (talk) 21:37, 9 October 2019 (UTC)

Plasmalogen
Does anyone have access to 10.1016/j.bbadis.2012.05.008? If so, could you please check whether a better version of the biosynthesis diagram may be extracted and uploaded? --Leyo 12:42, 21 October 2019 (UTC)


 * The problem is not access to the journal (you can use scihub which gives you any paper for free), the issue is the diagrams in the paper are copyrighted hence you cant just put them on wikipedia unfortunately. EvilxFish (talk) 12:27, 23 October 2019 (UTC)
 * Well, it is claimed as being copyrighted. However, I doubt that Figure 2 of that paper is above the threshold of originality. --Leyo 20:27, 24 October 2019 (UTC)

Need help tracing a citation
In Orthoacetic acid, there is this citation I can't, for the life of me, find what in the world that is supposed to be. ''Chem. Zeit.'' is an old abbreviation, but I can't figure out what it's supposed to be, other than probably something like Chemiker/Chemische Zeitung/Zeitschrift. If it's Chemiker Zeitung, the title of the article is surely in German rather than English (possibly "Über Ätzalkalischmelzen"). I think it's cited in, but I don't have access to it. &#32; Headbomb {t · c · p · b} 07:42, 24 October 2019 (UTC)
 * According to SciFinder: Chemicker Zeitung. An obscure, uncited article with no DOI.  That kind of ref should be struck. Dont know why anyone would ever cite that kind of nothingness.--Smokefoot (talk) 09:34, 24 October 2019 (UTC)
 * I can't find the ref. The substance in question is trisodium orthoacetate? SciFinder acknowledges neither the name nor the structure nor the claimed reaction. I wouldn't have thought it possible to make any of the orthoacetate anions (except a briefly lived intermediates), the mono-anion would just rearrange to give water and acetate.--Project Osprey (talk) 09:51, 24 October 2019 (UTC)
 * Chemiker-Zeitung, the title is listed in Chemisches Zentralblatt (kind of chemical abstracts in Germany in the past) Jg. 85 ; 1914 Systematisches Register of Band 1 with the no/page 1281  as Ätzalkalischmelzen. You may find the German abstract in .  JimRenge (talk) 09:57, 24 October 2019 (UTC)


 * Updated the citation to, although someone can feel free to provide one that's more useful. &#32; Headbomb {t · c · p · b} 16:03, 24 October 2019 (UTC)
 * The description of Feuchter´s publication in Orthoacetic acid appears to be misleading. According to the summary in the Chemisches Zentralblatt, Feuchter reacted Ethin with molten NaOH which resulted in sodium acetate and hydrogen as products. He postulated hydrogenorthoacetate and orthoacetate as intermediates.  JimRenge (talk) 21:58, 24 October 2019 (UTC)

Request for information on WP1.0 web tool
Hello and greetings from the maintainers of the WP 1.0 Bot! As you may or may not know, we are currently involved in an overhaul of the bot, in order to make it more modern and maintainable. As part of this process, we will be rewriting the web tool that is part of the project. You might have noticed this tool if you click through the links on the project assessment summary tables.

We'd like to collect information on how the current tool is used by....you! How do you yourself and the other maintainers of your project use the web tool? Which of its features do you need? How frequently do you use these features? And what features is the tool missing that would be useful to you? We have collected all of these questions at this Google form where you can leave your response. Walkerma (talk) 04:24, 27 October 2019 (UTC)

Shameful self promotion
Self promotion seems to be a big issue with plenty of computational chemistry articles. One only needs to look at various lists on articles like Molecular_dynamics or Force_field_(chemistry). Now some of these genuinely represent notable advances or popular forcefields in the case of the second example, however a great deal do not... Most are based on primary literature. Should we delete lists like this replacing them with short paragraphs based on review articles? EvilxFish (talk) 16:44, 28 October 2019 (UTC)
 * You should see the self-promotion in the synthesis areas. About two cases per week, I reckon.  Here is my approach:


 * 1) ) if the self-promotor adds their ref to an article lacking citations, I leave the ref, even if the self-promoting ref is primary. The theory is something is better than nothing.  Later, time-permitting, I try to find a secondary article to replace the promotor's article (I do not want self-promotors to feel rewarded).
 * 2) ) if the self-promoting article already has a foundation of a decent refs, I revert self-promotors.
 * 3) ) I check the history of self-promotors, and try to apply rules 1 and 2 above to their other edits.
 * The overarching worry is that some of these self-promotors, if treated in a welcoming way, will become good contributors. (the concept: "don't bite newbies" or something like that) Almost never have I seen self-promotors do good. Self-promotors come here to promote themselves, period.  It seems.
 * One surprise is that self-promotion is also practiced by senior, established scientists.--Smokefoot (talk) 22:06, 28 October 2019 (UTC)
 * I disagree in part with Smokefoot. Even if the article lacks other citations you should still delete self-promotion. It can be difficult to spot and if you ignore it you may eventually forget about it. If you feel that refs are necessary but can't find/access any then just flag it here, I'm sure we'll act in those circumstances. Of more concern to me are whole articles that appear to be self-promotional such as Matthew Linford or Sean Ekins, it feels like we have more articles on living chemists than dead ones, and that can't possibly be right. --Project Osprey (talk) 07:16, 29 October 2019 (UTC)
 * I feel as if the entire lists are not necessary, genuine advances will/should be covered in the history section of the article and they are just opening the door to easy abuse (not exactly hard to add an element to a list with a brief summary of your own work). Should we just delete the entire section? As for the bios let's nominate them for deletion, I will certainly vote in favour. Honestly wikipedia is a tool all academics use (whilst hypocritically condemning it as unreliable) and seeing them abusing it like this is very frustrating. EvilxFish (talk) 09:53, 29 October 2019 (UTC)
 * In Molecular dynamics any genuinely important refs from "Examples of applications" could be added back in at "Areas of application" or maybe "History" and the section deleted. In Force field (chemistry) "Popular force fields" could be largely copied over to "Comparison of force field implementations", maybe leave a short paragraph to cover the basics. That's just my opinion though. --Project Osprey (talk) 11:31, 29 October 2019 (UTC)

Example of the day
Here is a typical ref-spamming case from. This editor made these edits, today or in 2015: and a series of identical connected coils. The most common approach is to require that we have a magnetic field profile that varies in the $$z$$ direction such that the atoms experience a constant acceleration $$a=\eta a_{max}$$ as they fly along the axis of the slower. It has been recently shown however, that a different approach yields better results.
 * Zeeman slower
 * Zeeman slower (2015) edit

One of the recent advancements in the field is the merger of velocity map imaging with ion, and atom traps (MOT-VMI ), enabling to study electron emission from trapped cluster anions , and cold reactive collisions.
 * Photofragment-ion imaging:

One of the recent advancements in the field is the merger of velocity map imaging with ion, and atom traps (MOT-VMI ), enabling to study electron emission from trapped cluster anions , and cold reactive collisions.
 * Isotopic shift

Combined with velocity-map-imaging, a MOT was used to study the energetics of cold reactive collisions.
 * Magneto-optical trap

Exciting a beam of noble gas to the metastable state.
 * Inductively coupled plasma (2015 edit)

The Lambert W function have been recently shown to be the optimal solution for the required magnetic field of a Zeeman slower.
 * Lambert W-function (2015 edit)

--Smokefoot (talk) 12:27, 29 October 2019 (UTC)

Nomination for deletion
I have nominated a few articles chemistry related articles for deletion: MARTINI, Merck Molecular Force Field, X-Pol: the Explicit Polarization Theory, Please contribute to the discussion. Many thanks EvilxFish (talk) 16:06, 29 October 2019 (UTC)
 * MARTINI, has been reslisted in afd due to lack of consensus, please contribute to this discussion. EvilxFish (talk) 12:05, 7 November 2019 (UTC)

Fixing chemistry typos
At Correct typos in one click, you can fix typos or tag them for attention in a single click. However, there are a lot of chemistry terms that we need help with. Can anyone help out with checking whether the typos relating to chemicals are indeed typos? Thanks! Bellowhead678 (talk) 09:16, 6 November 2019 (UTC)
 * Well, one term that could be searched is "fully miscible" to be replaced with "miscible". But Wikipedian chemists would need to achieve consensus on whether miscibility is a "binary property": two liquids either are or are not miscible. IUPAC and Britannica diverge on the binary-ness of this definition. See Talk:Acetic acid.--Smokefoot (talk) 13:03, 6 November 2019 (UTC)
 * Thanks, I meant just for people to go through the existing list and check whether the suspected typos are indeed typos. Bellowhead678 (talk) 14:02, 6 November 2019 (UTC)
 * I am checking, but most of the chemistry terms are correct. I am adding some things to Wiktionary, but some may usefully be redirects. A question for people here for : 11β-trihydroxy-5α-ergost-22(E)-en-6-one, should the "E" be in parenthesis? and for ergost and ergosta we could do with a Wiktionary entry. (I think the original in the typos listing is correct though). Graeme Bartlett (talk) 22:01, 6 November 2019 (UTC)
 * Thanks, there are several additional lists to check through if you have gone through the main page. Bellowhead678 (talk) 22:22, 6 November 2019 (UTC)
 * So what lists are those? Are these with a number suffixed like Correct typos in one click/19? I did notice that this one click task fixed some typos I made. Graeme Bartlett (talk) 22:28, 6 November 2019 (UTC)
 * Yes that's right, you can see them at the top of the main list. Bellowhead678 (talk) 00:02, 7 November 2019 (UTC)
 * All chemistry words now look to be finished. When will more come? Graeme Bartlett (talk) 11:39, 8 November 2019 (UTC)
 * It's up to Uziel302 who runs the page, but probably once all the current typos have been fixed. (I would also like it to be sooner rather than later!) Bellowhead678 (talk) 11:55, 8 November 2019 (UTC)
 * , I uploaded new list now, based on words I found on chemistry books, so many will be chemistry typos.&#32; Uziel302 (talk) 01:04, 9 November 2019 (UTC)
 * Quite a few of these have already been fixed in the last few days, is this an out of date database dump?
 * Do we have a ref that the name is correctly laid out with the "E" in the middle of the name at all? Usual convention is that stereochemical designators go as a prefix not infix. DMacks (talk) 07:02, 7 November 2019 (UTC)

Category:Pyridoisoquinolines and ring counting
Hello, last month this CfD involving Category:Pyridoisoquinolines was closed with a consensus to merge manually to parents. All articles seem to be about nitrogen hetrocycles, no problem there, however I'm a bit confused whether all of them are appropriate for Category:Heterocyclic compounds (3 rings), as far as I can tell most have 5 rings. Could someone help me out and clarify how this ring counting is done? ‑‑Trialpears (talk) 22:12, 20 November 2019 (UTC)
 * We need a top-note on the Heterocyclic compounds (n rings) to say how the rings are counted. Is it the total number of rings, or the number of fused rings? I assumed the latter, in which case most of those compounds would go to both Heterocyclic compounds (3 rings) and Heterocyclic compounds (2 rings). This would be equivalent to tricyclo and bicyclo compounds. Graeme Bartlett (talk) 23:25, 20 November 2019 (UTC)

Nominated article on chemist for deletion.
Nominated Nathan C. Gianneschi for deletion, agreed when this was in draft space that it should be deleted. Please contribute to the discussion. EvilxFish (talk) 12:58, 23 November 2019 (UTC)
 * Once these biographical articles get into main space, they are almost impossible to stop. The article was created by someone at the same institution who had been promoting Gianneschi's work previously.  Its just the way that it is.  There are more useful ways of expending our energy here.  --Smokefoot (talk) 13:08, 23 November 2019 (UTC)
 * Regardless of the origin of the article, the subject appears to meet our notability guidelines so we should have an article about him. In my opinion, problems related to self-promotion or other conflicts of interest can be better solved by editing and improving the article rather than by deleting it.  -- Ed (Edgar181) 13:23, 23 November 2019 (UTC)
 * Basic XfD: Discussion should only be performed at Articles for deletion/Nathan C. Gianneschi. The creator should be notified. -DePiep (talk) 14:31, 23 November 2019 (UTC)

As an aside, I've long thought that WP:PROF needs to be radically tightened.--Project Osprey (talk) 21:03, 24 November 2019 (UTC)

Forging temperatures are wrong
The explanation on the forging temperature page is great, but the temperatures are wrong. It lists melting points, not forging temperatures. — Preceding unsigned comment added by 73.71.254.108 (talk) 04:46, 30 November 2019 (UTC)
 * Thanks, I changed the headings on Forging temperature to have correct info, even if it is useless for this article. Graeme Bartlett (talk) 09:56, 30 November 2019 (UTC)

Homework discussions on Talk
I confess to not being a fan of unsupervised homework assignments involving Wiki Chem articles, but it is what it is ... The aspect that I do question and have recently reverted are students using Talk pages to debate their edits. But maybe I am overstepping. My view: Talk pages are exclusively about improving articles and comments are addressed to the entire editor-universe. In contrast, homework discussion groups are: --Smokefoot (talk) 12:29, 7 November 2019 (UTC)
 * private conversations for a small working group (regular editors are not invited),
 * have an agenda that differs from Wikipedia's. The agenda is set by the instructor,
 * suffer from " the blind leading the blind" phenomenon: inexperienced editors instructing other inexperienced editors.


 * Well perhaps you should respond to their talk. Don't worry that they think it's private. Steer them onto what is appropriate for Wikipedia. Give an opinion on the proposed edits, even it it is try it out and if I don't like it I will remove it. Graeme Bartlett (talk) 21:46, 7 November 2019 (UTC)


 * I see now there is a main group chemistry class writing and drawing electron cloud images. See here https://dashboard.wikiedu.org/courses/MIT/Main_Group_Chemistry_(Fall)/students for the users and their pages. Though at this stage it looks like only Trivalent group 14 radicals has made it to article status. Graeme Bartlett (talk) 11:23, 24 November 2019 (UTC)
 * Sandboxes here: User:Tristan-Xin/sandbox=Nontrigonal pnictogen compounds; User:Alkemiya/sandbox=Ge(II) dications; User:SWeng19/sandbox=borenium User:BASkeel/sandbox=phosphaalkyne; User:Paperburner/sandbox=boroles; User:Tetraphenylporphine/sandbox/Triboracyclopropenyl Graeme Bartlett (talk) 10:06, 30 November 2019 (UTC)

Liquid Nitrogen
Recently an WP:ER was made at Liquid nitrogen to change the name of the 'first liquefied by'. I had a look through, but I know nothing about this subject, and I think a may have caused a WP:CIRCULAR effect. Can someone check and see what needs fixing at LN, Liquid oxygen and Raoul Pictet (if applicable)? Thanks for your help. - ChrisWar666 (talk) 19:09, 28 October 2019 (UTC)
 * Anyone? - ChrisWar666 (talk) 00:36, 1 December 2019 (UTC)

New organic chemistry 3D resources
Please see https://qrchem.net and https://rschemistry.com which were just announced. EllenCT (talk) 06:18, 6 December 2019 (UTC)
 * Thanks for the heads-up! Do you have any contact with the people working on the qrchem project? There is at least one pattern of substantial mistakes in some of the structures, which we found years ago and they are only now starting from the same square one. DMacks (talk) 16:50, 6 December 2019 (UTC)
 * There is a contact page in the menu dropdown or you could try contacting Garg directly thru UCLA. YBG (talk) 01:16, 7 December 2019 (UTC)

Input at alkine please
Please help decide what to do with alkine, thanks. The Language Learner (talk) 21:53, 11 December 2019 (UTC)

Non-helical models of DNA structure
I saw a Science Reference Desk question about this article. I've edited some of the references but have concerns about the content in this article. I've started a discussion at Talk:Non-helical models of DNA structure about my concerns. Any and all comments, edits, etc welcome. Thanks, EdChem (talk) 04:13, 13 December 2019 (UTC)

Question at hexavalent chromium
Would someone look at Talk:Hexavalent chromium Thanks. —[ Alan M 1 (talk) ]— 07:06, 26 December 2019 (UTC)

Citation bot is down
This handy tool is not working lately. See User talk:Citation bot.--Smokefoot (talk) 15:22, 28 December 2019 (UTC)

Tetrakis(methylammonium) hexachloroferrate(III) chloride
I notice that we have an article on tetrakis(methylammonium) hexachloroferrate(III) chloride, (or possibly ). The image accompanying the infobox is File:Tetrakis(methylammonium)hexachloroferratechloride.svg which shows the heachloroferrate with a 3&minus; charge on the iron centre, surrounded in what appears to be a square planar arrangement by methylammonium cations. This is (at best) misleading. Can someone provide a replacement? The uploader of the image was in 2010 but, according to his global contributions, he last contributed in April 2019. Thanks. EdChem (talk) 03:01, 3 January 2020 (UTC)
 * Looks ok to me. Its a strange one in that there free chloride in the lattice. Agreed that we dont want readers to reach any special conclusions about the location of the MeNH3+ cations in the picture. Some odd ducks (i.e. their notability being arguable) get written up in Wikipedia, and this is one.  It might be worthwhile if other editors look at double salt to make sure we are in consensus.  --Smokefoot (talk) 03:39, 3 January 2020 (UTC)
 * I think it's a mistake that the "3–" looks like it's associted with the Fe itself rather than the [FeCl6] cluster. It's actually weirder than that...not "free chloride in the lattice", but effectively "a [(CH3NH3)4Cl]3+ complex" (I just updated the article based on the cited X-ray structure ref). And based on that, I think it is a mistake to have all the methylammoniums and the chloride as loose separate ions. DMacks (talk) 03:45, 3 January 2020 (UTC)
 * H-bondingFeSO47aq.tif. The second coordination sphere consists of a water of crystallization and sulfate, which interact with the [Fe(H2O)6]2+ centers.]]Editors here are rediscovering the wheel: ammonium ions (those with N-H) virtually always H-bond.  Similarly, naked chlorides and esp fluorides virtually dont exist. M-NH3 complexes (metal ammine complexes) and M-OH2 complexes (metal aquo complexes)) universally engage in H-bonding to their anions (chloride, sulfate). Think hexamminecobalt(III) chloride.  H-bonding confers high lattice energies, i.e. have high m.p.'s, crystallinity, etc. By depicting these multiple H-bonding networks, the images would be very messy.  So, by tradition, the first coordination sphere is emphasized in our images, not the second.   So a few of us specialists might be satisfied with these fancier images, but the more general readers would be completely lost.  For tetrakis(methylammonium) hexachloroferrate(III) chloride, it doesnt matter because that salt is inconsequential. --Smokefoot (talk) 09:52, 3 January 2020 (UTC)
 * The edits made today by add further reasons to consider the existing image problematic.  The interstitial chloride ions are each surrounded by four methylammonium cations to form a  unit, something entirely obscured (at best) by the image, which implies no association between the chloride and methylammonium ions.  Smokefoot is correct about the coordination spheres and that the salt is relatively inconsequential.  The H-bonding is at best vaguely implied in the current image, however.  Surely we can think of a better representation without going to something so complicated that it is only comprehensible to chemists?  EdChem (talk) 11:58, 3 January 2020 (UTC)

Mct
I was looking at the article about Medium-chain triglyceride. It is very confusing; mixing information of triglycerides with information of acids and not relating them to each other and not clerify if one of them are natural and the other manmade.

The first sentence."Medium-chain triglycerides (MCTs) are triglycerides with two or three fatty acids" Is it true? Or maybe they are called diglycerides if they are with two fatty acids?

Sentence two. "Rich food sources for commercial extraction of MCTs include palm kernel oil and coconut oil" Are MCT really extracted from oils or is it more like medium chain fatty acids ( acids instead of triglycerides) are extracted and then exposed for chemical processes to make triglycerides? There might or might not be small amounts of triglycerides naturally occuring? But everything available in the market is manmade chemicals.

The marketing of MCT is huge. So it is important the wiki is not confusing us, the customers. From this article a customer might think that MCT is something natural. Please clerify.Oloffo (talk) 06:19, 7 January 2020 (UTC)
 * the first sentence definitely says it is a triglyderide, so if there are 2 medium chain acids only, then there must be a third of something else, probably a long chain fatty acid. Don't insert your full stop too early! Our article does not say how they are "made", but it is likely a simple extraction from a natural source. Why make the process expensive? Graeme Bartlett (talk) 12:07, 7 January 2020 (UTC)
 * Axona was intended for medical use and that was just fractionated palm kernel oil. I agree with Graeme Bartlett that natural sources seem the most likely.--Project Osprey (talk) 13:13, 7 January 2020 (UTC)

A link to a DAB page
Does anyone know which of the Wittig rearrangements is being referred to in Radical clock? Narky Blert (talk) 16:38, 20 January 2020 (UTC)
 * Went back to the 1976 JACS reference that the other reference was referring to, and appears to be a 1,2-Wittig (doi.org/10.1021/ja00422a041). Have fixed the disambiguation and added in the extra citation RRBinwood (talk) 17:31, 20 January 2020 (UTC)
 * Thanks! I was guessing 1,2, but it's good to be sure. (1976 is a bit after my time.) Narky Blert (talk) 18:43, 20 January 2020 (UTC)

Merck Index citations
There was consensus, back in 2015 (when I was Wikimedian in Residence at the Royal Society of Chemistry), for this proposal to replace three Merck templates (Merck11th, Merck12th, Merck13th) with Cite Merck Index; however that never seems to have happened. It needs the involvement of chemists, as in each case the data needs to be verified and if necessary updated. The there templates have 13, 20 and 8 (eight) transclusions respectively, so it's not a mammoth task. Can anyone oblige? Andy Mabbett ( Pigsonthewing ); Talk to Andy; Andy's edits 16:37, 18 January 2020 (UTC)
 * As I recall, the consensus among us chemists was that it was fairly dubious, which might explain the lack of action. I don't have access to the The Merck Index so I'm unable to help. --Project Osprey (talk) 21:04, 19 January 2020 (UTC)
 * You recall incorrectly; consensus is recorded at the first link in my post. Andy Mabbett ( Pigsonthewing ); Talk to Andy; Andy's edits 23:00, 20 January 2020 (UTC)

Draft:Lithium gold boride
Can someone please review this draft? My concern is that the only two references are by the same two authors, which is close to original research. Also, the draft does not list a CAS number, either in an infobox (which is not required and is not present) or in the text, and the lack of a CAS number for what would seem to be a compound makes me wonder about verifiability. Robert McClenon (talk) 02:59, 21 January 2020 (UTC)
 * For a draft it's not badly written but I don't think it's sufficiently notable. It's primary use is proposed as being "superconducting batteries" but that term is virtually unheard of in the literature. It's calculated as being a superconductor below ∼5.8 K which is far from impressive, it's actually worse than lead. Unless they can show a notable property I'd decline. --Project Osprey (talk) 10:16, 21 January 2020 (UTC)

Example: Tishchenko reaction
Many of our articles, especially ones about classic organic chemistry, start with heavy reliance on historic references. We can all be grateful to the editors that put these articles in place and felt it appropriate to pay homage to the pioneers of chemistry. But realistically, moderrn readers are unlikely to want to consult the original work by Vyacheslav Tishchenko when they read about the Tishchenko reaction. They would rather read not So I suggest that we aim shift the historic, original references out of the ledes and into other sections such as "Other reading" or "History", etc. The early refs will be retained, but an overall effort will be to support the lede with broad, modern sources, often textbooks like Carey or March.--Smokefoot (talk) 01:39, 6 February 2020 (UTC)
 * V. E. Tishchenko | title= О действии алкоголятов алюминия на альдегиды. Сложного-эфира конденсации, как новый вид уплотнения альдегида. |trans-title=On the effect of aluminium alkoxides on aldehydes.  Ester condensation, as a new kind of aldehyde condensation. | journal=Журнал Русского Физико-Химического Общества (Journal of the Russian Physico-Chemical Society) | volume=38 | year=1906 | pages=355–418 | url= https://books.google.com/books?id=iy9CAQAAMAAJ&pg=PA355#}} ; 482–540. (in Russian)
 * В. Е. Тищенко and Г. Н. Григорьева (V. E. Tishchenko and G. N. Grigor'eva) (1906) "О действии амальгамы магния на изомасляного альдегида" (On the effect of magnesium amalgam on isobutyric aldehyde), Журнал Русского Физико-Химического Общества (Journal of the Russian Physico-Chemical Society), 38 : 540–547. (in Russian)
 * М. П. Воронҝова and В. Е. Тищенко (M. P. Voronkova and V. E. Tishchenko) (1906) "О действии амальгамы магния на уксусный альдегид" (On the effect of magnesium amalgam on acetic aldehyde), Журнал Русского Физико-Химического Общества (Journal of the Russian Physico-Chemical Society), 38 : 547–550. (in Russian)
 * В. Тищенко (V. Tishchenko) (1899) "Действие амальгамированного алюминия на алкоголь. Алкоголятов алюминия, их свойства и реакции." (Effect of amalgamated aluminium on alcohol.  Aluminium alkoxides, their properties and reactions.), Журнал Русского Физико-Химического Общества (Journal of the Russian Physico-Chemical Society), 31 : 694–770. (in Russian)
 * Sounds reasonable. I would tend to include cites to the originals in a sentence such as:
 * The reaction is named for Vyacheslav Tishchenko, who first reported it in 1906.&lt;ref>[cite the original works]&lt;/ref>
 * I could even envision having that sentence in the lede, since it does summarize a bunch of details that would be in the article, placing the reaction in the context of person and time. I would want to include "name reaction" in that sentence (unpiped, since it's a topic known by that term) but I can't think how without being redundant ("a name reaction named for..."?). DMacks (talk) 07:34, 6 February 2020 (UTC)
 * Depends. For non-eponymous pages like toluene I don't mind (providing we don't create a section that's just "Is named after..."). If the reaction or substance is named after someone it seems odd not to mention who in the lead. --Project Osprey (talk) 09:33, 6 February 2020 (UTC)

Organising the metals and nonmetals
FYI: Here's a link to an open access article of the same name, authored by me, and recently published in Foundations of Chemistry. Sandbh (talk) 04:06, 12 February 2020 (UTC)
 * So does that mean that you should avoid citing this work (in Wikipedia), since doing so would be a COI? Smokefoot (talk) 19:49, 15 February 2020 (UTC)

Please see WP:SELFCITE. Sandbh (talk) 21:28, 15 February 2020 (UTC)

Script to detect unreliable sources
I have (with the help of others) made a small user script to detect and highlight various links to unreliable sources and predatory journals. The idea is that it takes something like and turns it into something like
 * John Smith "Article of things" Deprecated.com. Accessed 2020-02-14.
 * John Smith "Article of things" Deprecated.com. Accessed 2020-02-14.

It will work on a variety of links, including those from cite web, cite journal and doi.

I'm still expanding coverage and tweaking logic, but what's there already works very well. Details and instructions are available at User:Headbomb/unreliable. Questions, comments and requests can be made at User talk:Headbomb/unreliable. &#32; Headbomb {t · c · p · b} 13:01, 19 February 2020 (UTC)

4f sub-shell involvement in lanthanum
Is this possible?

MacKay et. al (2002, p. 256) speculate that:

"The one case in which contributions to the bonding from the f orbitals is possible is in complexes of the heavier elements in which the coordination number is high. Use of the s orbital, together with all the p and d orbitals or one valency shell, permits a maximum coordination number of nine in a covalent species. Thus, higher coordination numbers imply either bond orders less than unity or else use of the f orbitals In addition, certain shapes (such as a regular cube) or lower coordination number also demand use or f orbitals on symmetry grounds. These higher coordination numbers have only become clearly established recently, but their occurrence in lanthanide or actinide element complexes suggest the possibility of f orbital participation.  Examples include the 10-coordinate complexes mentioned above, LaEDTA(H2O)4 and Ce(NO3)52- or 10-coordinate La2(CO3]3.8H2O; 11-coordinate Th(NO3)4.5H2O (coordination by four bidentate nitrate groups and three of the water molecules); and the 12-coordinate lanthanum atoms in La2(SO4)3.9H2O-with twelve sulfate O atoms around one type of La atom position."

— MacKay KM, MacKay RA &Henderson W 2002, Introduction to modern inorganic chemistry, 6th ed., Nelson Thornes, Cheltenham

OTOH, Parish (1977, p. 151) firmly rules this out:

"Two features are particularly striking in the chemistry of the 4f—elements, Viz. (a) the uniformity of the +3 oxidation state and the small number of other oxidation states, and (b) the irregularity of structures and occurrence of high coordination numbers. In the compounds described here, coordination numbers of six, seven, eight, and nine have been mentioned, and in other compounds ten- and even twelve-coordinate metal ions are found, eg. in La2(SO4)3.9H20 and (NH4)2Ce(NO3)6. It is tempting to think that the f-orbitals must be involved in the bonding, since the maximum number of hybrid orbitals which can be constructed from an s-p-d -set is nine, and to obtain eight bonding orbitals directed towards the corners of a cube (as in C602) requires at least one f-orbital. There is, however, no evidence to suggest that the f-orbitals are involved at all in the bonding, and even ligand-ﬁeld effects are extremely small. All the compounds appear to be essentially ionic, with very little covalency involving even the 6s- or 6p-orbitals. The curious structures and high coordination numbers are similar to those found with other large cations (e.g. salts of Ba2+ or Pb2+) and are presumably a result of the optimisation of electrostatic forces. The large internuclear distances necessitated by the radii of the cations will cause the electrostatic energy per pair of ions to be relatively small, despite the high cationic charge, and many such pairs must be formed to achieve a suﬂiciently large lattice energy. Similarly, the large radii diminish considerably the polarising effect of the +3 charge which would otherwise be expected to lead to considerable covalency." (p. 151)

— Parish RV 1977, The metallic elements, Longman, London

Thank you, Sandbh (talk) 22:51, 14 February 2020 (UTC)
 * With the first 4f6s2 excited state at 1.8842 eV, well within the range of chemical bond energies? Yes, of course. Double sharp (talk) 00:25, 15 February 2020 (UTC)

Are there any other views in this matter, particularly the contradiction between the two cited references? Sandbh (talk) 03:25, 28 February 2020 (UTC)

Issues with CAS Number and ECHA InfoCard in my Infobox
I asked this same questions in my Sandbox talk page User_talk:Gabriele_Segalla but I'm been suggested to ask this WikiProject Chemistry page too. I have created a Sandbox User:Gabriele_Segalla/sandbox for a chemical and I have created an infobox as well. In the infobox I have two issues: Thank you. --Gabriele Segalla (talk) 08:01, 20 February 2020 (UTC)
 * 1) The CAS number does not work, by clicking it I get (correctly) in the Common Chemistry Website but it states Your Search Returned Zero Results. How can I handle this?
 * 2) The Input from Wikidata section of the Template:Chembox states that "ECHA InfoCard ID is read from Wikidata", yet I do not see the ECHA InfoCard in the infobox. Again, how can I handle this?
 * Regarding the CAS# Commons Chemistry lookup, it fails for virtually every chemical; I wouldn't worry about it. I do not know anything about ECHA in particular and very little about wikidata item lookups technical details. DMacks (talk) 08:13, 20 February 2020 (UTC)


 * Can we just remove the link to Commons Chemistry? For me at least, all it does is make the CAS N° difficult to copy and paste. --Project Osprey (talk) 10:16, 20 February 2020 (UTC)
 * I would support unlinking the CAS. Maybe the link was more appropriate in the early days of the ChemBox validation project when we collaborated with some CAS-related external entities, but that was a decade or more ago and now it's not a positive (useless) and is a negative (providing a link to a useless target and interfering with a different useful action like copying). DMacks (talk) 16:57, 20 February 2020 (UTC)


 * The ECHA infocard is only going to appear in the chembox, when the page is linked to the Wikidata item. For drafts and sandboxes this is not a good idea. Graeme Bartlett (talk) 21:48, 20 February 2020 (UTC)

✅ here. See Menthyl nicotinate. By now, ECHA infocard is used as a ref, and also appears in the Chembox because WikiData exists (by cooperation). CAS RN reference is sourced well in this instance (manually). However, we should revisit the 'bad automated CAS NR reference' footnote later on. -DePiep (talk) 22:28, 3 March 2020 (UTC)

Draft:1,6-hexanediol diacrylate
Can someone please work up the infobox for this draft? I will accept it once the infobox is done. Robert McClenon (talk) 21:52, 3 March 2020 (UTC)
 * Done, added basic info. -DePiep (talk) 22:20, 3 March 2020 (UTC)
 * I revised and created an article in main space. Will add image later.  Its a good addition. --Smokefoot (talk) 22:30, 3 March 2020 (UTC)
 * eh, did you copy/paste, really? That's not honorable to the creator User:Robert McClenon, and not wiki-OK. From Draft to Mainspace is a Move (=Rename) thing. Could you take an other look at your process? -DePiep (talk) 22:35, 3 March 2020 (UTC)
 * (wrong H in title)
 * , please correct this asap, including the attributions/history. -DePiep (talk) 22:42, 3 March 2020 (UTC)
 * User:DePiep - I was not the creator of the article; I was only a reviewer. That was User:GRALISTAIR.  But I have requested a history merge.  Robert McClenon (talk) 01:40, 4 March 2020 (UTC)
 * My excuses to for my mistake. With the hist merge, I think everything is fine. -DePiep (talk) 08:08, 4 March 2020 (UTC)
 * My excuses to for my mistake. With the hist merge, I think everything is fine. -DePiep (talk) 08:08, 4 March 2020 (UTC)

GRALISTAIR (talk) 02:57, 4 March 2020 (UTC) I am not too worried over who gets the credit for creating the article as long as it gets published so others can improve - which looks like is already happening.
 * I messed this thing up, apologies. One of these years ...--Smokefoot (talk) 12:06, 4 March 2020 (UTC)

Synthetic diamond featured article review
I have nominated Synthetic diamond 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. Sandy Georgia (Talk)  23:26, 20 March 2020 (UTC)

Maybe these pages need to be merged
BTW, I've linked List of isomers of decane to C10H22 pages of French and Chinese in wikidata. I wonder if this page is best in the form of a list or in the form of disambiguation.--Htmlzycq (talk) 07:26, 6 February 2020 (UTC)
 * C9H20 and List of isomers of nonane
 * Stilbene and Diphenylethylene
 * On its face, these seem like reasonable proposals, but when I look closer:
 * List of isomers of nonane is a MOS mess...links in headers and duplication of links. It uses strictly systematic names, which is good if that's what you have, but it's not a proper listing in DAB terms because some of the articles do not use systematic name as their title (DAB says we don't pipe) and they are almost all redlinks (hard to find our actual aricles). And why only include structural (vs stereo) isomers, given that sometimes for other chemical-sets each separate stereoisomer of a compound has its own article. I'm not sure that list article should exist, but if it does, it fits a different niche than the formula one. DMacks (talk) 07:48, 6 February 2020 (UTC)
 * I think if we connected List of isomers of nonane to fr:C9H20 in frwiki, which lists all stereo isomers, it will help to improve this page.--Htmlzycq (talk) 11:34, 6 February 2020 (UTC)
 * 1,1-Diphenylethylene is not a stilbene or stilbenoid in the classical sense. So stilbene is a defined set that is the parent of one major larger class of compounds, and diphenylethylene includes something that is not part of that class. So neither is a subset of the other.
 * So I don't think either is a case to merge, based on Set index articles and related DAB/list guidelines. DMacks (talk) 07:48, 6 February 2020 (UTC)


 * I reckon that C9H20 may as well redirect to List of isomers of nonane. However I sould like to see the list sourced to prove that it is a complete list. Some other languages have rticles on every isomer. But their content and sourcing certainly don't prove that every isomer is notable. So the number of links should be cut. The MOS mess was fixed easily, as those links in the headers are not useful. Graeme Bartlett (talk) 02:40, 9 February 2020 (UTC)
 * I think C9H20 may redirect to list of isomers of nonane because the formula C9H20 represents saturated 9-carbon alkanes. --Leiem (talk) 05:01, 21 March 2020 (UTC)

Should we consider amine oxides as zwitterions?
Gold Book says so, another editor disputes it...I would appreciate additional chemists' eyes and input at the zwitterion article (Talk:Zwitterion seems to be at an impasse) regarding the scope/definition of the topic and the authority of references for it. DMacks (talk) 02:51, 30 March 2020 (UTC)
 * Just so we are all on the same page, here is the Goldbook definition:


 * "Neutral compounds having formal unit electrical charges of opposite sign. Some chemists restrict the term to compounds with the charges on non-adjacent atoms. Sometimes referred to as inner salts, dipolar ions (a misnomer). E.g. H3N+CH2C(=O)O− ammonioacetate (glycine), (CH3)3N+–O− trimethylamine oxide."
 * Possible compromise language: "Trimethylamine oxide can be classified as as zwitterion, but this description is debatable because the charges are located on adjacent atoms (N and O)." --Smokefoot (talk) 12:13, 30 March 2020 (UTC)
 * That's reasonable. Could you give that a try at the article, or somehow else try to work some sense into an editor who persists in rejecting cited sources in place of uncited content? DMacks (talk) 03:41, 2 April 2020 (UTC)

Chemistry of ascorbic acid and Vitamin C: Wikidata items and interlanguages links
Please see Talk:Chemistry of ascorbic acid. --Mezze stagioni (talk) 12:58, 9 April 2020 (UTC)