Wikipedia talk:WikiProject Chemicals

Stylized depiction of chemical structures

IMHO the dot structures found e.g. in Croconate blue, Croconate violet, Oxocarbon, Peroxydicarbonate, 1,3-Bis(dicyanomethylene)squarate and 1,2-Bis(dicyanomethylene)squarate do not comply with MOS:CHEM. Leyo 15:09, 18 April 2023 (UTC)

Agreed. They seem to have been added by Jorge Stolfi. The one I checked was done in 2010. Jorge seems to still be active (last edit this March) so perhaps he would like to change the drawings to more conventional ones, or I can do that if he is no longer interested. Mike Turnbull (talk) 16:23, 18 April 2023 (UTC)

I have now redrawn the individual compounds Croconate blue, Croconate violet, 1,3-Bis(dicyanomethylene)squarate and 1,2-Bis(dicyanomethylene)squarate. Another I've changed is 2-(Dicyanomethylene)croconate. The oxocarbon article has lots of drawing that are consistent, although not aligned with usual conventions, and I've left that alone, along with peroxydicarbonate. Mike Turnbull (talk) 15:59, 21 April 2023 (UTC)

Though perhaps the different image version should have a different name. Graeme Bartlett (talk) 12:10, 22 April 2023 (UTC)

@Graeme Bartlett I would have done that if any of the articles in which the diagrams were used had a reason to retain the old images but I could see no justification for that in MOS:CHEM. Of course, if the earlier versions were needed, they can easily be obtained from the Commons history and I would have no objections if my overwrites were reverted in that case. Mike Turnbull (talk) 17:19, 22 April 2023 (UTC)

That's not allowed by commons guidelines (commons:COM:OVERWRITE). Images that are substantively different need to be uploaded at a different filename. Please undo/revert those changes there. DMacks (talk) 18:15, 22 April 2023 (UTC)

c:COM:SPLIT exists to handle those cases while preserving history and avoiding unnecessary complications. –LaundryPizza03 (dc̄) 18:39, 22 April 2023 (UTC)

Thanks for the link. I've put in the splitting requests. Mike Turnbull (talk) 20:49, 22 April 2023 (UTC)

For the record, in order of amount of total work required: someone else handling your split-request > you re-uploading at a different name and reverting the old filename's contents > you filing a split-request. DMacks (talk) 03:42, 23 April 2023 (UTC)

I don't feel strongly about my diagrams in general. If someone wishes to redo them, please go ahead. But may I suggest better ways to spend that time. For example, last I checked there were dozens of fatty acid diagrams, used in dozens of articles, with the omega labels just wrong.
However, the new croconate diagrams, in particular, seem less informative than mine, and somewhat misleading. First, the convention that "unlabeled corners and ends are carbon atoms", while fully internalized by chemists, is quite confusing to a large section of the target public. Moreover, the new diagrams hide the aromatic character of the ring, and the "fractional" bonds and negative charges on the attached carbons that makes it work. (At least, that was the structure I gleaned from the papers I read.) The new image is just one of the "resonance" forms, isn't that so? And "resonance" is just a hack to fit the actual messy orbital truth into the old model of integer valences, localized integer charges, and binary bonds; isn't that so? For these reasons, shouldn't my diagrams (or others equivalent to them, e.g. 3D ball-and-stick) be kept as alternate representations, at least?
Finally, please note that uniformity of style and looks -- which is basically what the MOS is about -- has very little value for the reader. A commercial paper encyclopedia (dictionary, textbook, etc) must have strictly uniform style and typesetting, because otherwise the prospective buyer, leafing through it, would think that it is a mash-up of texts by disparate authors, randomly edited, with no plan and no oversight by a chief editor. But Wikipedia is a mash-up of texts by disparate authors, randomly edited, with no plan and no oversight by a chief editor. Thus, uniformizing its style and typesetting is downright dishonest: it leads the reader to think that Wikipedia is more reliable and complete than it actually is...
Methinks that the only "manual of style" that an editor needs to know is "look at a few other articles on related subjects, try to imitate what is good in them, and try to fix was is bad."
All the best, Jorge Stolfi (talk) 21:37, 24 April 2023 (UTC)

We chemists usually show the most representative resonance structure when possible (we can all agree that we aren't going to emphasize minority resonance structures). True, one needs significant knowledge to understand nuances of resonance structures. With the major resonance structure at least a reader can count electrons, check for conformance of trends in oxidation states and electron counting rules (octet rule, etc), and anticipate sites on a chemical that will be basic/nucleophilic vs acidic/electrophilic vs saturated/unsaturated. One cannot readily undertake those analyses with stylized images.

In terms of "fully internalized by chemists, is quite confusing to a large section of the target public." Yes indeed. One needs a significant knowledge to read encyclopedia articles on specialized topics in chemistry. That is the way it is: Wikipedia presents facts. At the same time, we rely on discussions like this to review and perhaps recalibrate our communication styles. --Smokefoot (talk) 21:57, 24 April 2023 (UTC)

Of course it is OK to use specialized jargon (textual or graphical) in those parts of articles that will be only of interest to specialists. However, the target readership of Wikipedia (or any general encyclopedia) definitely includes every non-specialist who read the term "geomagnetic jerk" or "neutrino oscillation" and wants to know what that is. Thus every article should strive to satisfy those readers, to the level of detail that will be useful to them, as well as the specialists. All the best, Jorge Stolfi (talk) 15:21, 25 April 2023 (UTC)

@Jorge Stolfi You make some interesting points. My view is that no encyclopaedia, even Wikipedia, can comment on the complexity of aromaticity and resonance forms in every article in which it is relevant. We do so occasionally, as at the archetype, benzene, where the diagram I've placed here is included and does cover these issues.

Benzene Representations

For better or worse, our MOS:CSDG specifies using a molecule editor and ACS drawing conventions. All these standard editors give Kekule-style representations of aromaticity and chemical drawings in Wikipedia mainly conform to these widespread standards also seen in Chemspider and Pubchem and virtually every professional chemical publication. My main concern with your drawings of the croconate examples, aside from the MOS, was that they didn't sufficiently emphasise that these are dianions: no charges are shown (see example below) and that outweighed the fact that they show the aromaticity better, albeit somewhat unconventionally.

Croconate violet, ACS conventions

Croconate violet, Stolfi

However, I was certainly in error when I overwrote your files and that has now been undone. There may well be a case for expanding the Pseudo-oxocarbon anion article to use both types of diagram. Currently it has only mine. Mike Turnbull (talk) 11:46, 25 April 2023 (UTC)

Problem images

Jorge Stolfi I'm not sure if you are aware, but there are ways of flagging images that have issues on Commons (like these fatty acid diagrams). Sadly these don't yet feed into our Alerts list --Project Osprey (talk) 09:00, 25 April 2023 (UTC)

Thanks! Jorge Stolfi (talk) 15:10, 25 April 2023 (UTC)

• Commons:WikiProject Chemistry/Deletion requests
• Commons:Category:Disputed chemical diagrams, /expired
• Commons:Category:Low quality chemical diagrams, /expired
• Commons:Category:Verified chemical structure diagrams
• Commons:Category:Media needing chemical classification

Re: TOXNET has moved

(Continuation of Wikipedia talk:WikiProject Chemicals/Archive 2023#Re:_TOXNET_has_moved)

I just finished working on this. I moved {{HPD}} to {{CPID}} and updated the links on all pages that used it. Enjoy! — Garrett W. {☎ ✍} 18:54, 4 May 2023 (UTC)

Also just finished going through insource:/householdproducts\.nlm\.nih\.gov/ and updating all the broken links in those. — Garrett W. {☎ ✍} 20:30, 4 May 2023 (UTC)

Thank you. What about deleting the redirect Template:HPD? --Leyo 22:23, 14 May 2023 (UTC)

Sure, I could propose it for deletion.

(edit) Done. — Garrett W. {☎ ✍} 06:14, 15 May 2023 (UTC)

Theanine

Discussion at Wikipedia talk:WikiProject Medicine#Tea component theanine and its putative cognitive effects. SandyGeorgia (Talk) 12:40, 21 May 2023 (UTC)

Organofluorine article titles

I am trying to make sense of our articles on various classes of organofluorine compounds. We of course have organofluorine chemistry as the broad concept article, which is fine pursuant to WP:CHEMGROUP. But then we have Fluorocarbon, which at first seemed like it was a content fork and should be merged, analogous to chlorocarbon redirecting to organochlorine chemistry, but the focus of that article is really perfluorocarbon compounds, i.e., compounds with only C-F bonds. But, we also have perfluorinated compounds, which seems to focus on compounds again with C-F bonds in place of C-H bonds, but those also containing heteroatoms/functional groups. And then we have Hydrofluorocarbon, which are compounds with a C-F bond that retain at least one C-H bond.

If this seems like an appropriate way to separate out the content, then I propose moving fluorocarbon to perfluorocarbon, since the former term is too vague and should really redirect to the broader organofluorine chemistry article. But, that increases the confusion between perfluorocarbon and perfluorinated compounds. Hatnotes may be the answer there. Any thoughts? Mdewman6 (talk) 00:12, 27 May 2023 (UTC)

I support the proposed reorganization. About 10 years ago, User:Shootbamboo, now inactive, created some fluorocarbon-related articles. The activity seemed to be motivated by that editor's interest in raising awareness of PFOS and related "forever chemicals" (which redirects to Per- and polyfluoroalkyl substances). One issue was whether organofluorine compound contained any C-H bonds or not. In any case, it seems timely to revisit the organization of our organofluorine subtopics.--Smokefoot (talk) 03:11, 27 May 2023 (UTC)

The main reason to keep hydrofluorocarbon separate is because the important ones are refrigerants with less potential to damage the ozone layer. Perfluorocarbon and perfluorinated compounds are essentially the same thing: although it could be argued that the latter should include SF₆ and UF₆ etc. so maybe the title to keep should be the first one to emphasise that the article's scope is only within organic chemistry. I agree that organofluorine chemistry is the correct place for the main topic, covering everything that has at least one C-F bond. I'm not sure where PFAS should fit, though. PFOS is clearly a single substance (+ salts/esters) that merits its own article. Mike Turnbull (talk) 10:50, 27 May 2023 (UTC)

The article title Fluorocarbon is probably owed to the IUPAC Gold Book entry. Despite of that, moving this article to perfluorocarbon would make sense IMHO. BTW: The respective article in de.wikipedia is de:Perfluorcarbone. --Leyo 21:00, 27 May 2023 (UTC)

Quinuclidine derivs

better

misleading.

Maybe a minor point but I have noticed that almost all of the cinchona alkaloids (quinine etc) are or were depicted with the quinuclidine group drawn with one skewed (CH₂)₂ backbone. The thing about quinuclidine is that it is rigid and all-chair.--Smokefoot (talk) 14:23, 27 May 2023 (UTC)

A likely explanation is that the misleading form is much easier to draw. If you wish to improve and replace the existing images then please go ahead - but I expect the situation might be replicated in the literature. The two forms are sufficiently different to the eye that some readers might struggle to reconcile the depictions. Would there be any merit to adding a note somewhere on the page? Project Osprey (talk) 18:58, 27 May 2023 (UTC)

Good points. It does seem that the drawing on the left captures the correct geometry however. And adding a remark on the page that the CH2's are eclipsed might be a good idea. --Smokefoot (talk) 19:44, 27 May 2023 (UTC)

One of the reasons that professional organic chemists are likely to use the "misleading" structure is that it is the only one correctly recognised by chemical drawing packages and conforms to the "rules" originally set out by MDL Information Systems and implemented in their molfile format, still widely used today. Perspective drawings involve drawing at least one bond with a gap (as seen in "better") or one ends up with an ambiguous image illusion. Both drawings have their place, depending on context. Mike Turnbull (talk) 16:50, 31 May 2023 (UTC)

Good article reassessment for CS gas

CS gas has been nominated for a good article reassessment. If you are interested in the discussion, please participate by adding your comments to the reassessment page. If concerns are not addressed during the review period, the good article status may be removed from the article. Onegreatjoke (talk) 01:07, 28 May 2023 (UTC)

Shall synthesis routes to various end products via the same intermediate be counted as routes to that intermediate?

Hello, I would like to account for methyl nitrite. It was an intermediate product in a synthesis of dimethyl oxalate. Including that synthesis, shall all routes via methyl nitrite be counted as routes to methyl nitrite? According to a previous discussion, yes it shall:

Any intermediate in an industrial process is a commercially important chemical in its own right, -- DMacks (talk) 15:15, 23 July 2017 (UTC)

-- Ktsquare (talk) 01:30, 8 June 2023 (UTC)

Requested move for Alpha hydroxy acid

An editor has requested for Alpha hydroxy acid to be moved to another page. Since you had some involvement with Alpha hydroxy acid, you might want to participate in the move discussion (if you have not already done so).

Help and mediation needed at Eucalyptol

I am involved in a revert battle at eucalyptol and the issue requires mediation because we are just going back and forth. It would be nice to resolve this struggle within the chemistry project. My case at least is going to be stated on Talk:Eucalyptol. --Smokefoot (talk) 13:08, 10 June 2023 (UTC)

Chembox or DrugBox mismatch

I came across this article (Sinclair, Gabriel; Thillainadarajah, Inthirany; Meyer, Brian; Samano, Vicente; Sivasupramaniam, Sakuntala; Adams, Linda; Willighagen, Egon L.; Richard, Ann M.; Walker, Martin; Williams, Antony J. (24 October 2022). "Wikipedia on the CompTox Chemicals Dashboard: Connecting Resources to Enrich Public Chemical Data". Journal of Chemical Information and Modeling. 62 (20): 4888–4905. doi:10.1021/acs.jcim.2c00886.) which is worth looking at for those in our sub-project. It raises a number of issues with some of our articles, which appear not to be sorted out yet. For example what is the connection between JWH-210 and [[]JWH-182]]? or why does JWH-203 include CAS no for JWH-204? But some were fixed, eg user:ChemConnector changed smiles on JWH-359. It appears that articles with multiple substances, may be indicated by multiple infoboxes or indexing, on non-indexed multiple strings or RNs cause trouble matching things up. So what can we do to make the Wikipedia data more useful and accessible for large database matching? Graeme Bartlett (talk) 02:33, 19 June 2023 (UTC)

Somewhat related: if you go to this resource [1] and select 'Browse Errors' you see a list of all pages with SMILES errors, chemboxes without SMILES and duplicated SMILES. Handy for error checking. --Project Osprey (talk) 09:55, 19 June 2023 (UTC)

Thanks, that list is giving me more SMILES values to fix. Graeme Bartlett (talk) 07:51, 20 June 2023 (UTC)

As you'll know, some of the authors of that article are active Wikipedia editors. One thing that has been done since it was published is that the DTXSID (and ECHA Infocard) values are not maintained in the Chembox/Drugbox but instead are maintained centrally in Wikidata. The linkage between Wikidata's QID and external IDs makes it more likely the correct one-to-one relationship can be maintained. I'd be happy to help out fix any ongoing issues but I think we need guidance from Walkerma etc. as to the current priorities. Mike Turnbull (talk) 10:58, 19 June 2023 (UTC)

I'm travelling at the moment (actually at a Romanian airport right now), so it's hard for me to follow through right now, but I'm sure we could set something up to fix things systematically once I get home. The main coordinator of the project is user:ChemConnector, but other co-authors are more familiar with Wikidata and should probably get involved. Thanks, Walkerma (talk) 08:56, 21 June 2023 (UTC)

Just to give an hint regarding the current discussion in WD about identification of molecules. If WD solved the question of stereisomers and position isomers (every different form has its own item), the question for zwitterions and tautomers is still open. This affects the generations of InChI/InChIKey/SMILES reprsentations and therfore the correct identification in the databases. Another welle frequent problem is the definition of covalent/ionic bond for salts and complexes. Current discussion to solve these problems is available here. Snipre (talk) 12:17, 14 August 2023 (UTC)

Sulfur dioxide and climate change pages related to it

Hello all! I normally participate over in Wikipedia:WikiProject Climate Change, but there is one matter which overlaps substantially with the scope of this project.

Essentially, I think you all know that sulfur dioxide has a reflective, anti-greenhouse effect in the atmosphere. This makes it a popular subject for all sorts of speculation about ways to address warming and even the "true" extent of current warming, and this speculation has produced a lot of Wikipedia articles with a lot of overlap as well. By my count, we currently have:

• sulfur dioxide

• sulfate aerosols

• stratospheric sulfur aerosols

• stratospheric aerosol injection

• solar geoengineering

• global dimming

They all have substantial overlap with each other. Some of it is justified (i.e. stratospheric aerosol injection is technically only one of several possible ways to do solar geoengineering, even if it is by far the most practical one), some not so much, and altogether, managing so many overlapping pages is not practical, so they weren't really managed. As I discovered earlier this year, pretty much all of them were out of date - sometimes by whole decades, with most of citations from 2000s. Considering that this is a subject of active interest, with some of these pages consistently scoring hundreds views per day, this is hardly an idle concern.

I have more-or-less managed to get global dimming up to date by now, and at least managed to update the lead and first paragraphs of solar geoengineering (the rest is still a semi-active battleground of active claims and counter-claims about competing proposals that'll take a while to untangle). However, I do not see much point in retaining a stratospheric sulfur aerosols page, when all it provides is very general (and currently very dated) information, some of which belongs in [stratospheric aerosol injection, some in global dimming, and some can most likely just be folded back into sulfur dioxide article. Sulfate aerosols is likely not needed for similar reasons.

What would you say about this proposal? I raised it on WP:ClimateChange earlier, but it unfortunately doesn't have enough editors to discuss every single matter in detail. I hope this is sufficiently close to the project's scope to be discussed here. InformationToKnowledge (talk) 19:55, 21 June 2023 (UTC)

Well, with regards to " I think you all know that sulfur dioxide has a reflective, anti-greenhouse effect in the atmosphere." Huh? This is a group of chemists. Reflectivity is hardly of interest in the chemistry world. But more to the point, my experience is that controversial topics like water fluoridation spawn many articles on related topics. Without speculating on why this spawning and splitting arises, it is undesirable because curation of the articles is awkward and all sorts of fringe perspectives slip in. So, assuming that you are not a jerk and science denialist, you should consolidate those articles. It could be a major service to our readership.--Smokefoot (talk) 20:29, 21 June 2023 (UTC)

I will add that sulfur dioxide in itself would not be "reflective" and is probably a greenhouse gas in itself, as it would have additional absorption in the infrared. However once it is oxidised to sulfur trioxide, it would nucleate cloud droplets, and then have the properties you say. If you think a couple of articles are unneeded then you can merge the content, and turn them into redirects in the appropriate sections. Graeme Bartlett (talk) 00:28, 22 June 2023 (UTC)

Since you have agreed with the notion, and no-one else had objected, it is now done. Sulfate aerosols and [Stratospheric sulfur aerosols]] have been merged into the closest appropriate articles, and a lot of information had been streamlined (not to mention better referenced and illustrated.) InformationToKnowledge (talk) 17:22, 28 June 2023 (UTC)

What do we think about Guidechem.com citations?

Recently a variety of far-eastern IP addresses have been adding plausible-sounding sentences to chemical articles, with citations to guidechem.com, so that as of today this insource search gives 54 hits. A few others have already been reverted by Project Osprey, e.g. here today, MadeOfAtoms e.g. here today and myself. The website to which all these link is not one on our list of chemical databases but if its homepage here is to be believed it lists over 9 million chemicals from 30,000+ suppliers and its MSDS such as this one for serotonin are nearly as comprehensive as the corresponding pubchem entry. Indeed, guidechem.com may have used pubchem as their source. Clearly guidechem.com is not a reliable source as normally defined since it is a database with only a few named sources. It has some interesting quirks, such as (from the serotonin "other information") Serotonin is the baby boomer of neurotransmitters..... What should our attitude to this website be? Mike Turnbull (talk) 11:32, 29 June 2023 (UTC)

I wasn't aware there was a pattern. Perhaps this is an attempt at Search engine optimization, by getting Wikipedia to cite guidechem.com --Project Osprey (talk) 12:01, 29 June 2023 (UTC)

Incidentally, that quotation comes directly from this chapter in a book. Mike Turnbull (talk) 12:05, 29 June 2023 (UTC)

I did not add that site to the list of chemical databases as I considered it to be a marketer. For the same reason I did not add chemical suppliers or manufacturers. But if someone else added it to that list, I would not remove it. As a reference it would be inferior, and better to cite something closer to where the information came from, even a manufacturer. Graeme Bartlett (talk) 21:56, 29 June 2023 (UTC)

This website shows info that is mostly copy-pasted from what seem to be reliable sources, usually without attribution. For example the pentane edit adds text that was copy-pasted from Patty's Toxicology (2012), without attribution. One could consider this to be useful info in the pentane case, but it would need a link to the proper source and paraphrasing to avoid copyvio. Seems worse than useless given the info on pubchem. –MadeOfAtoms (talk) 22:28, 29 June 2023 (UTC)

A few guidechem additions popped up on my watchlist lately, not even written coherently sometimes. Clearly spam IMO. Nuke it all. DMacks (talk) 05:18, 6 July 2023 (UTC)

I've now 31h-blocked 42.98.200.240, and will not hesitate to block others based on this seeming consensus here. DMacks (talk) 05:22, 6 July 2023 (UTC)

That were flagged by WikiProject Spam, including cross-wiki to multiple languages, in 2011! We also had a discussion here at that time about blacklisting it (Wikipedia talk:WikiProject Chemicals/Archive 2011#Blacklisting http://www.guidechem.com/), involving 4 admins at least somewhat supporting doing so. DMacks (talk) 05:29, 6 July 2023 (UTC)

Thanks User:MadeOfAtoms for helping to clean up the uses. A bunch of named accounts are now continuning this behavior across multiple-wikis and are getting g-locked for spam. I filed an enwiki blacklist request, no prejudice against upgrading it to global blacklist. DMacks (talk) 16:37, 8 July 2023 (UTC)

Thanks, @DMacks for the archive discussion and your other actions. MadeOfAtoms has done a good job of the cleanup so my insource search now shows just 12 instances. I'll help with removing the rest of these and any new ones that appear. Mike Turnbull (talk) 17:31, 8 July 2023 (UTC)

Thank you for blocking and cleaning, and I'm happy to help out. –MadeOfAtoms (talk) 17:59, 8 July 2023 (UTC)

I just removed the last handful from mainspace. DMacks (talk) 18:28, 9 July 2023 (UTC)

Journal links that go to another vendor

When editing Claisen condensation, the following refs were encountered:

• Claisen, L. (1887). "Ueber die Einführung von Säureradicalen in Ketone". Berichte der Deutschen Chemischen Gesellschaft. 20 (1): 655–657. doi:10.1002/cber.188702001150.
• Hauser, C. R.; Hudson, B. E. Jr. (1942). "The Acetoacetic Ester Condensation and Certain Related Reactions". Organic Reactions. 1: 266–302. doi:10.1002/0471264180.or001.09. ISBN 0471264180.

The URL's direct to zenodo.org and www.scribd.com, which seems undesirable because we are promoting an intermediate vendor. But maybe these sites are useful by providing access to articles that would otherwise be behind a paywall. I also increasingly see refs that link to a ResearchGate's URL. I have been removing these links to Research Gate because they do not seem to offer any advantage vs the journal URL, but maybe I shouldn't. Comments are welcome.--Smokefoot (talk) 14:34, 9 July 2023 (UTC)

I agree that we should not be generally preferring any intermediate vendor, and the DOI (or similar token) leads to the publisher already. Therefore, we should not have direct URL links to the publisher's site (this is already against citation guidelines). However, if there is a valid third-party archive it might be useable if it does not violate the license of the content. Scribd in particular is a problem because it's essentially a free upload site, and therefore ripe for copyright-violations--it is a violation of WP sitewide guidelines to link to such things. Specifically, the Organic Reactions ref is a 1942 publication and therefore typically still protected by copyright, so that link is not acceptable. Zenodo is more careful with the content it hosts. Specifically, the Berichte ref is an 1887 publication, and therefore no longer protected by copyright (public domain due to age), so it is not a violation to link to a copy of it. The publisher's own site (via DOI) paywalls it, so there is added value to linking to the Zenodo archive (it correctly identifies the content as "open access"). DMacks (talk) 17:40, 9 July 2023 (UTC)

The Royal Society of Chemistry in the UK has recently partnered with ResearchGate to make their open-access journals more accessible. So links to that resource are going to become more frequently used. For articles with DOI that link to a paywall, any ResearchGate URL offering open access should be welcomed. That said, I assume that the RSC's own OA journals will be accessible from the DOI directly, so an additional ResearchGate link seems unnecessary. Mike Turnbull (talk) 10:37, 17 July 2023 (UTC)

Silylgermane

I'm currently at in impasse with user:Bernardirfan over the fate of Silylgermane. I think the page should be deleted, they feel otherwise. For my part I think the compound fails our usual notability guidelines. It is produced by mixing two highly toxic and phyrophic gasses, Germane and Silane, both of which are hugely important in semiconductor synthesis. I think silylgermane was produced to answer the question of "what happens if you combine them" - but beyond this I can find no actual application. It's just a bit of chemical esoterica. Many current references are below our usual standard. I've decided to bring the matter here rather than Pages for Deletion as I suspect technical rather than procedural arguments will decide the outcome. Project Osprey (talk) 20:29, 16 July 2023 (UTC)

There are many articles about certain chemical compounds that have no application at all, they are just an esoteric compounds, even non-existent compounds, which are just of academic interest and for scientific research, all across Wikipedia, yet, they are not deleted. I would feel discriminated if my article Silylgermane was rather deleted, than kept for future improvement. But let's wait the consensus to decide the fate of my article. Bernardirfan (talk) 22:47, 16 July 2023 (UTC)

For weird reasons, I am kinda into germane, and I can say that H3SiGeH3 is real and well characterized. The early paper by (Nobelist) MacDiarmid is shaky, agreed. There are a lot of theory papers, but they will calculate anything it seems. One team really nailed this stuff though. Now about notability, that is a tougher question. Some of us (me) have added all sorts of esoteric compounds to this project, so I am not a good judge. In any case, here is a primary ref to silylgermane doi 10.1021/ja051411o. The compound is mentioned (only) in a recent review as follows "Extended tetrelane hydrides containing both Si and Ge centers (e.g., the butane analogue H3Ge-SiH2–SiH2–GeH3) have been developed for CVD ..." Matthew M. D. Roy, Alvaro A. Omaña, Andrew S. S. Wilson, Michael S. Hill*, Simon Aldridge*, and Eric Rivard (2021). "Molecular Main Group Metal Hydrides". Chem. Rev. 121: 12784–12965. doi:10.1021/acs.chemrev.1c00278.{{cite journal}}: CS1 maint: uses authors parameter (link). --Smokefoot (talk) 23:05, 16 July 2023 (UTC)

In Bernardirfan's defence, I think I might just be bias again hydrides heavier than Calcium. They seem to occupy some weirdly privileged position as automatically valid topics for articles - when in practice they are often utterly impractical to make, with few (often disagreeing) reports of their properties and no practical applications.

I don't for one moment doubt that this stuff exists. Anyone who can do this sort of chemistry (without resorting to picking bits of burning glass out of their face) must be a good chemist. Existence by-itself is not sufficient for notability. I'm fine with esoteric when it's interesting - but this stuff is exactly what you would expect. Structure and physical properties (bpt) are about midway between Disilane and Digermane. Tedious. Project Osprey (talk) 00:07, 17 July 2023 (UTC)

Then why articles about the compound Gold heptafluoride, which has no practical applications at all, and even non-existing compounds like Osmium octafluoride and Xenon octafluoride and many, many more similar articles across Wikipedia, writed by many editors, are notable? I consider them notable too. By the way, please, do not delete all those articles, because Wikipedia would be truncated by deleting a huge amount of important, notable information and knowledge. I think the user:Project Osprey might just be biased against hydrides heavier than Calcium hydride. But I am not biased against them, I am open minded for any esoteric and hypothetical compounds. Even hypothetical compounds are notable according to me and other editors who obviously approved all those articles about those compounds. Many structural and physical properties of Hexadecane are about midway between Tetradecane and Octadecane, and some structural and physical properties of Stannane are about midway between Germane and Plumbane, just as some structural and physical properties of Silylgermane are about midway between Disilane and Digermane, so what, other editors and me don't see any problem about all those midway articles. All those compounds are still notable since they are obviously approved (do not delete them too). Bernardirfan (talk) 00:44, 17 July 2023 (UTC)

Patrol approval does not necessarily mean that the topic really is notable. Please be wary of hypothetical compounds. AFD is still possible. But I prefer to have articles rather than delete them, so it's mainly the misleading articles that I will want to eliminate. Currently there is an outbreak or actinide oxyhalide articles. But the substances do seem to exist even if very unimportant. What I hope is that the next big important advance in materials or chemicals will already have an article on Wikipedia. Graeme Bartlett (talk) 10:03, 17 July 2023 (UTC)

Thank you. Bernardirfan (talk) 10:10, 17 July 2023 (UTC)

I reckon that Silylgermane is notable based on two references that have substantial content. However the article has several lower quality database references that could be improved. Graeme Bartlett (talk) 23:20, 16 July 2023 (UTC)

Some articles of questionable notability are poorly written or thinly supported. If these editors really want to help the project they could contribute to widely read topics, say, on polymers or chemicals in everyday life (boring white solids). Although these weakly notable articles seem harmless (and maybe they are), one problem is that these editors get invigorated and keep at it. So we get more and more such cruft. Another problem is that these often questionable articles do not reflect well on Wiki Chem. IMHO.--Smokefoot (talk) 01:50, 17 July 2023 (UTC)

FAR

I have nominated Hydrochloric acid for a featured article review here. Please join the discussion on whether this article meets the 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" in regards to the article's featured status. The instructions for the review process are here. Keres🌕Luna ^edits! 16:39, 25 July 2023 (UTC)

User:Louisajb/UCL-1530

What about moving back this stub into the main space? Does anyone have access to SciFinder to look for a CAS RN? Leyo 12:48, 3 August 2023 (UTC)

It's on Chemsider here (InChIKey=SXDHPHPRCINSFL-XUQYBVARSA-P) but they don't quote a CAS number. Chemspider has another drawing as a neutral but even that doesn't have a RN (InChIKey=SXDHPHPRCINSFL-XUQYBVARSA-N). I'm in doubt as to whether is stuff is really notable enough to warrant an article. The InChIKey leads to one patent hit for US20040229803 but that was abandoned more-or-less as soon as it was published. Pubchem doesn't come up with much. Mike Turnbull (talk) 13:39, 3 August 2023 (UTC)

CAS 172998-23-1, SciFinder shows a total of 4 refs. --Project Osprey (talk) 15:03, 3 August 2023 (UTC)

Thank you. --Leyo 00:38, 4 August 2023 (UTC)

Credibility bot

As this is a highly active WikiProject, I would like to introduce you to Credibility bot. This is a bot that makes it easier to track source usage across articles through automated reports and alerts. We piloted this approach at Wikipedia:Vaccine safety and we want to offer it to any subject area or domain. We need your support to demonstrate demand for this toolkit. If you have a desire for this functionality, or would like to leave other feedback, please endorse the tool or comment at WP:CREDBOT. Thanks! Harej (talk) 18:06, 5 August 2023 (UTC)

Fats vs fatty acids

Merging of polyunsaturated fatty acids and polyunsaturated fats might be a well intentioned, but it is a dumb or at least naive idea. Fatty acids are fatty acids, fats are triglyberides and related materials. What next? See Talk:Polyunsaturated fat. Can someone with time and skills please undo this mess brought on by user:Amakuru. --Smokefoot (talk) 21:10, 5 August 2023 (UTC)

@Smokefoot: I literally just told you I did not "bring on the mess". I did not do that merge. If you want it reverted, I'll be happy to do so, but please stop casting WP:ASPERSIONS and assuming bad faith. Thanks  — Amakuru (talk) 21:11, 5 August 2023 (UTC)

Requested move at Talk:Β-Butyrolactone#Requested move 16 August 2023

There is a requested move discussion at Talk:Β-Butyrolactone#Requested move 16 August 2023 that may be of interest to members of this WikiProject. ModernDayTrilobite (talk • contribs) 16:06, 25 August 2023 (UTC)

Classify molecular formula set index articles as list or disambiguation pages?

Hello! I going through the many list / disambiguation pages that fall under the WPChemicals umbrella. A good number of these fall under Category:Molecular formula set index articles, and only have a handful of entries on each page, which is justifiable in this situation. However, what I wanted to ask about is "how should these articles be categorized inside the wikiproject?" When going through these talk pages, there seem to be many different "project-category outcomes" that each of these articles fall into, seemingly arbitrarily. Some of the set index articles are listed as part of the WikiProject, yet may contain articles that are not part of the WikiProject. The vice versa is also true; some of the articles are NOT a part of the project, while all of the indices on the page are. But, this is kind of getting ahead of the program. The main question is which outcome would be most correct with dealing with these set index articles?

The status quo is all over the board, but just perusing for a bit led to the following categorization of common outcomes for set index articles (each of which contain articles that are all part of WPChemicals):

In WikiProject Chemicals:

• List class / Low importance (and project lists & index) = Talk:C3H7I, Talk:C4H2, Talk:C5H9NO3S, Talk:C8H18N4O2
• List class / Low importance (and project lists) = Talk:C4H10S, Talk:C7H6O6, Talk:C9H11FN2O5, Talk:C11H10N2O2, Talk:N4O
• List class / Low importance (no project lists) = Talk:C2H2, Talk:C4F8, Talk:C5H11Cl, Talk:C9H12N2O6, Talk:C11H15ClO2
• Dab class / Low importance (and project dab) = Talk:BrO, Talk:C6H14O3, Talk:C7H15Cl2N2O4P
• Dab class / Low importance (no project dab) = Talk:C3H3NS, Talk:C21H34O3
• Dab class / Low importance (no project dab, yet has project lists for some reason) = Talk:C2Cl3F3
• Dab class / NA importance (and project dab) = Talk:C4F6, Talk:C8H10N2O3S
• Dab class / NA importance (no project dab) = Talk:C8H5NO6, Talk:C11H17BrNO2

Not in WikiProject Chemicals:

• Just in project dab = Talk:C7H7NO, Talk:C8H6O, Talk:C9H17N, Talk:C10H8O, Talk:C10H15NO3
• No talk page entirely = Talk:C10H10O5, Talk:O2+

Going through this category was a strange experience, as its seemingly possible to click on any molecular formula index article, and be given a surprise box of wikiprojects on its talk page. Because there's a couple thousand or so of similar pages, it may be worth using a bot or script to go through and align the appropriate set index articles for WikiProject Chemicals, and/or any other concerned WikiProjects (Disambig, Lists, etc). The first thing though, I think, is figuring out the appropriate way to deal with these. Utopes _{(talk / cont)} 19:05, 8 September 2023 (UTC)