Wikipedia talk:WikiProject Chemistry/Archive 50

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Proposed RFC on nonmetal categories

Colleagues

I've drafted this RFC at WP:EMEN, here.

I'd be pleased to hear your thoughts re NPOV, coverage, and anything else.

"Moderately active nonmetals" was suggested to me by Peter Nelson after I asked him about "light nonmetals". From speaking with other non-WP chemists, and chemistry teachers, some of them have heard of CHONPS, CHNOPS, and SPONCH. One said, "Yes, I have used CHNOPS for years." @EdChem:, a chemist, is familiar with it too.

The RFC hasn't gone live yet. I intend to run it from the nonmetal talk page.

thank you
--- Sandbh (talk) 07:14, 6 November 2020 (UTC)

Sandbh, I think there are some issues.
  • NPOV: Presenting the option "other nonmetals" with the comment "meaningless", or commenting simply a link to the literary genre "popular science," appears to me to convey a point of view. There are others where the comments are much more arguments than a balanced / unbiased summary, such as "[i]mplies halogens, noble gases are ≠ nonmetals."
  • The RfC does not mention the metalloids, presumably as they are a separate category. Should this be mentioned? If so, and presuming astatine is classified as a metalloid, is the modification "non-metal" still required after halogen.
  • How should commenters respond if they don't support two or three categories, or don't agree with the ones proposed?
  • What about a "keep the status quo" option?
  • "Depending on the source,[13][14][15][16][17] essential (nonmetal) elements include from 5 to 9 of P; HCNOSCl; F(?)SeI; Si" is confusing to me. I don't understand how any source could not include at least the six elements C, H, O, N, P, and S as essential non-metals given that they are all necessary for amino acids / proteins or RNA / DNA or both. Further, you have listed 11 elements.
  • In Table 3, what is an "anonymous nonmetal"? Is this meant to be anomalous?
EdChem (talk) 10:23, 6 November 2020 (UTC)

Thanks EdChem.

  • NPOV. My comment on the category name e.g. "other nonmetals" was intended to provide a concise snapshot on a possibly relevant consideration. From past discussions at WP:ELEM, nobody likes "other nonmetals" since it doesn't mean anything apart from appearing to treat the subject nonmetals as leftover, forgotten, or orphan nonmetals. Might you have an alternate suggestion for a comment?
  • My comment for the category name "orphan nonmetals" was "popsci". I.e. I found it in a popular science book. While I personally think it's a clever name, I'm less comfortable about relying on a popsci book. Put another way, if I hadn't mentioned this then someone else, no doubt, would've complained about it during the RFC proper.
  • The category name "nonmetals" for HCNOPSSe appears to infer e.g. that the "noble gases" are not nonmetals. Some authors categorise all group 17 elements, using the term "halogens". The nonmetals to the left of the halogens are then categorised as "nonmetals". Does this mean halogens are not nonmetals? I feel this is a relevant consideration.
  • Metalloids. For brevity, the RFC 2-part question doesn't refer to metalloids, as they belong to one of the three "super-categories" of metals; metalloids; and nonmetals. They are however mentioned in the preamble, and in Table 3, for context.
  • We show At as a PTM. Thus, the halogens are composed of four nonmetals, and one metal, where "halogens" is an IUPAC collective name for F–At. It follows that F–I are halogen nonmetals.
  • Alt-editors. Editors who don't support 2, or 3 categories, or who don't agree with the ones proposed could comment in the discussion section. I'll look closer at this. But an RFC should be concise, and I don't want it to be any longer that it already is; the scope creep light is flashing.
  • Status quo is the 2 categories option.
  • Anonymous nonmetals. In table 3, I call them (HCNOPSSe) that as they have no single standout category name in the literature. Since it caused confusion, I'll change it.
  • I suppose the "anomalous nonmetals" might be HHeCNOFNe ^_^

--- Sandbh (talk) 23:39, 6 November 2020 (UTC)

I will be overhauling the Phosphinidene page

A 90% completed draft is in my sandbox. I plan to upload my changes within the next few days.

--T2g eg (talk) 19:12, 9 November 2020 (UTC)

@T2g eg: Great project and thank you! Comments:
  • Spare us your calculations. Wiki does publish primary research. Primary research is removed summarily.
  • Try to focus on reviews and books per our guidelines: WP:SECONDARY and WP:TERTIARY.
  • details: the great majority of phosphinidine complexes are clusters, if you havent noticed. Perhaps you might relabel your article complexes of terminal phosphinidines. Wikipedia has an article Phosphinidene. Be careful with the word "stable". Happy editing.--Smokefoot (talk) 20:40, 9 November 2020 (UTC)
@Smokefoot:
  • Based on my and my WikiEdu course instructor's understanding, reproducing calculations from primary literature does not constitute as original research.
  • I have included some reviews and books in my reference list, but given how niche the topic is, primary sources are necessary.
  • I kept two sentences about phosphinidene clusters at the end of this section (these were from the previous version of the page), but I am not personally interested in expanding this area. Others are free to contribute to this section.

Update to peer review page

Hi all, I've boldly updated your project's peer review page (Wikipedia:WikiProject Chemistry/Peer review) by updating the instructions and archiving old reviews.

The new instructions use Wikipedia's general peer review process (WP:PR) to list peer reviews. Your project's reviews are still able to be listed on your local page too.

The benefits of this change is that review requests will get seen by a wider audience and are likely to be attended to in a more timely way (many WikiProject peer reviews remain unanswered after years). The Wikipedia peer review process is also more maintained than most WikiProjects, and this may help save time for your active members.

I've done this boldly as it seems your peer review page is pretty inactive and I am working through around 90 such similar peer review pages. Please feel free to discuss below - please ping me ({{u|Tom (LT)}}) in your response.

Cheers and hope you are well, Tom (LT) (talk) 23:45, 14 November 2020 (UTC)

Rhondite

Is this notable? Is this stub WP:OR? Bearian (talk) 02:14, 20 November 2020 (UTC)

I probably can't judge whether it is notable enough, but I want to point out that one of the links in the "Further Reading" section, though currently broken, leads to a Bloomberg article specifically mentionning rhondite (updated link: https://www.bloomberg.com/news/articles/1992-01-19/steel-with-much-more-muscle). More secondary and tertiary sources are definitely needed, though. --ElMagyar (talk) 10:33, 20 November 2020 (UTC)

AFD: Biodegradable athletic footwear

Wikipedia:Articles for deletion/Biodegradable athletic footwear. I thought this would be automatically entered onto our 'Article alerts' page when I flagged it - but it turns out that it's not assigned to this project, so I'm doing it manually. Opinions are gratefully sought --Project Osprey (talk) 23:25, 20 November 2020 (UTC)

Periodic table has an RFC

Periodic table has an RFC for possible consensus. A discussion is taking place. If you would like to participate in the discussion, you are invited to add your comments on the discussion page. Thank you. --- Sandbh (talk) 01:38, 21 November 2020 (UTC)

Hexachloroethane

Application in a specific protest was added into the article and I do not believe that inclusion of such into the chemical page is WP:DUE. Discussion at Talk:Hexachloroethane Graywalls (talk) 02:33, 10 December 2020 (UTC)

Samarium(III) sulfide

Samarium(III) sulfide came to my attention as an unsourced stub that nonetheless meets our notability guidelines. It appears to be a semiconductor that is mostly studied as a thin film. Example sources include:

  • Kumbhar, V. S.; Jagadale, A. D.; Lokhande, C. D. (15 July 2013). "Supercapacitive evaluation of soft chemically deposited α-Sm2S3 thin films". Journal of Power Sources. 234: 107–110. doi:10.1016/j.jpowsour.2013.01.078. ISSN 0378-7753.
  • Marin, Chris M.; Wang, Lu; Brewer, Joseph R.; Mei, Wai-Ning; Cheung, Chin Li (25 June 2013). "Crystalline α-Sm2S3 nanowires: Structure and optical properties of an unusual intrinsically degenerate semiconductor". Journal of Alloys and Compounds. 563: 293–299. doi:10.1016/j.jallcom.2013.02.082. ISSN 0925-8388.
  • Aruga, Atsushi; Tsujimi, Sachiko; Nakai, Izumi (1996). "Crystal Structure of Samarium Sesquisulfide, .ALPHA.-Sm2S3". Analytical Sciences. 12 (1): 151–152. doi:10.2116/analsci.12.151.

I'll be too busy to expand this article right now. –LaundryPizza03 (dc̄) 10:10, 7 December 2020 (UTC)

I have expanded the article, but in return can you please stop nominating chemical categories for deletion? Graeme Bartlett (talk) 22:13, 11 December 2020 (UTC)

Is The Faraday Institution within your ambit?

They are all about batteries, it seems, and have no WP article. One of their employees has been given the job to write about them, but everything online is all based on their website, press releases, etc. No history seemingly is documented, for instance. However, I would guess that the Institution has archives on hand.

The unfortunate employee may not manage to get an article approved. If anyone out your way happens to be into batteries and history, they may want to help out on Draft Talk:The Faraday Institution or at the draft creator's Talk. In fact, anyone near London could even contact the Institution about their archives and try to gain access to them. risk offending the draft's creator.

I'm from the USA and from the insect and plant world, so I'm not that drawn to writing about the Institution; it just amazes me when something big and prominent is so hard to write about on WP.--Quisqualis (talk) 22:00, 25 December 2020 (UTC)

Plagiarism in Elsevier book

The newly published book is "The Periodic Table: Nature's Building Blocks An Introduction to the Naturally Occurring Elements, Their Origins and Their Uses" By J. Theo Kloprogge, Concepcion P. Ponce, Tom Loomis. isbn=9780128215388, 0128215380. Much of the chemistry content is taken directly from Wikipedia without attribution. I wrote to the lead author who responded: "We have used many different resources to write our book including the chemistry as reflected in the extensive References and Futher reading lists at the end of the chapter." Note: Wikipedia is not acknowledged. I also contacted Elsevier, the publisher, but it is a very large organization, so I am not optimistic that they will address the problem. It is inevitable that some losers would eventually repackage and take credit for our content, but it is still unfortunate. What can you do? Not much probably. If anyone has the time to independently inspect on-line versions of the book, you might notify Elsevier of any overlap that you detect. --Smokefoot (talk) 16:28, 28 December 2020 (UTC)

Better contact some journalists:having an article in a newspaper spotting that problem will force the publisher to react. Snipre (talk) 20:34, 29 December 2020 (UTC)
Some examples of copied or at least closely paraphrased content are in User_talk:Smokefoot#Possible copyright issue with an Elsevier book (should have posted my comment here instead of there) Is there some noticeboard where to report these kinds of plagiarism cases? Obvious WP:CIRCULAR potential here, if someone decides to cite this book when editing Wikipedia. jni(talk)(delete) 16:06, 2 January 2021 (UTC)
I wrote to Retraction Watch. This book is nearly 1000 pages with lots of color images. My guess is that it was expensive to produce. Lead author claims to see no problems. The other two authors did not respond to my query. Elsevier is tough to crack. They dont exactly have a "report plagiarism here" link. --Smokefoot (talk) 16:22, 2 January 2021 (UTC)
@Nitraus: Email received this AM from Elsevier: "I wanted to let you know that we investigated the plagiarism claim and found that many large sections throughout the book were taken from Wikipedia or similar sources, as you indicated. We are in the process of making the book unavailable on all of our platforms and withdrawing it for sale from all of our resellers.
Thank you very much for bringing this to our attention, and so quickly, so that we could remove it right away.
Best wishes for 2021," Many thanks for User:Nitraus for finding the problem.--Smokefoot (talk) 17:57, 6 January 2021 (UTC)
Really a sad case, I have to just wonder how the authors didnt see this as an issue. You would assume that they would be familiar with the ethics of scientific writing having the positions they do. At least Elsevier acted. --Nitraus (talk) 18:08, 6 January 2021 (UTC)
Good questions. Someone spent real money on this 1000-page color-illustrated book. My guess is that two senior authors wanted to showcase their geo-knowledge and their rock collections. And the junior author, a young woman in a Philipine university, was stuck with generating the chem content.--Smokefoot (talk) 18:30, 6 January 2021 (UTC)
Full credit to you both for finding this and getting it dealt with. You might be able to get the whole story on 'In the Pipeline' or some-such, I'm sure a non-covid story would go down well at the moment. It serves as a interesting example: plenty of people still consider Wikipedia's articles to be of suspect quality, but in this case the book's editor/reviewer was reading them without knowing it and found the content good enough to be in a scientific textbook. It's a sign perhaps that this project is generating very good work in places. --Project Osprey (talk) 10:50, 7 January 2021 (UTC)

List of compounds

I was reviewing the list of compounds and I noticed that a lot of super heavy compounds like SgCO6 are not in there and I don't know how to wikicode without doing to much damage. Not to mention some article are very vague about whether its a compound or not like NhOH. Can someone help? UB Blacephalon (talk) 21:57, 18 January 2021 (UTC)

The longest half life of Seaborgium is 14 min, for Nihonium it's about 10 seconds. What can we sensibly say about the chemistry of such elements - other than that it is brief? I doubt any 'normal' data exists as only vanishingly small amounts could ever be made (such levels of radioactivity would make bulk samples even less stable). What we're left with is fleeting observations, modelling, and to a certain extent conjecture. --Project Osprey (talk) 22:19, 18 January 2021 (UTC)
Um, the fact that it exists and how its made? Besides NhOH and SgCO6 exist to I think, the article isn't very clear on that. plus fermium has to have some and einsteinium does too. Can't we put that in there? UB Blacephalon (talk) 03:50, 19 January 2021 (UTC)
Hi Blacephalon. You seem to be very interested in the chemistry of the super-heavy elements. For the reasons of very short half-life already mentioned, there is unlikely to be sufficient information in the chemical literature to make them independently WP:NOTABLE (in the very specific sense used in Wikipedia). For that reason, I feel that any discussion of them should go in the article about the relevant element. Any list of compounds such as at Glossary of chemical formulae should, for similar reasons, stick to those which have articles in Wikipedia (although I see that currently some are red-linked). There are at least 200 million organic chemicals in databases (see List of chemical databases) and clearly Wikipedia cannot have an article for each one, any more than it can have an article for each person on the planet. Mike Turnbull (talk) 17:04, 20 January 2021 (UTC)
I actually am very interested in the chemistry of ANY radioactive element. However I do suggest that we do something straight out of Wikipedia Pokemon and merge them into a group. But since I was previously told that it'd be too long, maybe we can group them by element rather than just grouping them anywhere. I feel like the lists of elements and compounds needs some work to be done on it and its gotten to the point to where we need to group it another way, ya know? UB Blacephalon (talk) 17:20, 20 January 2021 (UTC)
OK, can you make a specific proposal based on whichever example you think shows your idea the best? Mike Turnbull (talk) 17:55, 20 January 2021 (UTC)
Well, I think we should do 118 lists of every element and every compound it has and maybe a little more info? Just an idea. UB Blacephalon (talk) 19:22, 20 January 2021 (UTC)
I figured you were going to say that but it seems overkill to say the least ;-) Are you the one who is going to type up the 200+ million each for hydrogen and carbon — and do you think readers will be interested? That's what databases are for and we already have Chemspider and Pubchem freely available, with links back to Wikipedia articles where one exists. I hoped you might suggest the more feasible task of listing the few well-characterised compounds known for the transuranics, where the list could go into the element's article. Mike Turnbull (talk) 10:35, 21 January 2021 (UTC)
I really haven't thought of that. Well to solve this, maybe we can shorten those by not only linking the article like you said, but link an article of all the Hydrogen and carbon compounds if wikipedia has one. I was hoping to showcase the actinide series and the transneptunium series (Am I using that right?) by doing this but maybe we could add a separate column for any well known uses it might have. What ideas did you have? UB Blacephalon (talk) 18:14, 21 January 2021 (UTC)

I've looked into this in more detail now and I fear that we are in more of a mess than I thought. Take [[Category:Inorganic molecular formulas]] for example. One might have hoped that all Wikipedia articles on inorganic compounds would be in this category via the re-direct pages for their molecular formula. This is only true for a minority. So while we find Uranium dioxide there as UO2, Uranium hexafluoride as UF6 is not included, although the redirect page exists. I suspect that the same may be true for organic compounds as well: the redirect from the molecular formula may exist but the formula itself may not be in [[Category:Molecular formulas]]. Furthermore it turns out to be impossible to search Pubchem, Chemspider, or eMolecules to find all compounds containing an element like Nh, your original example, Blacephalon. That's because the substructure searches are designed to be run on (part) organic drawings and the first step gets too many hits when the search doesn't contain anything except a rare element. So I'm afraid such list articles, even if warranted in some cases, will be impossible to generate in practice without great effort that is arguably not justified. Mike Turnbull (talk) 14:20, 22 January 2021 (UTC)

So is it really not possible to have all the compounds in Wikipedia? Maybe we can rearrange and add to the list. Can't we take from what wikipedia says about the compounds and update the lists there? UB Blacephalon (talk) 17:40, 22 January 2021 (UTC)
You will also have to decide inclusion criteria. For the super heavy elements most compounds are hypothetical, and have no information published on them. There is no upper limit to complexity so there will be an infinite number of possible compounds. Wikipedia reflects published information, so we will have to be limited to that. That may include real or hypothetical compounds. And as mentioned before, the page has to be useful. We also have limits on the size of a page. For more extensive lists of substances, use wikidata. However I am working on many list articles containing mixed anion compounds, most of which are not-notable themselves. For common anion compounds of fleeting elements, they may get a mention in the article on the anion. I will also note that there are a lot of molecules of two elements that are not stable in bulk. These may exist in stars or be important theoretically, or even may need an article to say why the substance is not stable. Graeme Bartlett (talk) 21:24, 22 January 2021 (UTC)
Well we can maybe make a separate list of that in the future, but for now let's focus on compounds that we can prove are real first. I'm not sure what anions are (I think its negatively charged compounds but I could be wrong) but we could use some of that info to make the article. How about we can split the list up into organic compounds (H-Mo and Ru-Ra) and inorganic (Tc and Ac-Og) compound lists. We could exclude the H and C compounds by putting some of the most well known ones and moving on. What do you think? UB Blacephalon (talk) 22:49, 22 January 2021 (UTC)

Structural inconsistency among acetylacetonate complexes

I noticed that there is an inconsistency in the structural formulas in Category:Acetylacetonate complexes, namely concerning the dashed bonds:

Is anyone aware of a IUPAC recommendation on how to draw the lines?

In addition, there are different types of ball-and-stick images, i.e. with and without dashed lines, e.g.:

--Leyo 09:51, 12 January 2021 (UTC)

the real problem is that at least two structures are incorrect. No way Ba is 4-coordinate and the Dy complex would typically has additional Lewis bases.--Smokefoot (talk) 15:42, 12 January 2021 (UTC)
I made the Dy-complex diagram solely based on its given chemical formula ("Dy(acac)3 itself"). I agree it's likely to have additional ligands (looks like the commercial product is the hydrate but I don't know the hydration number). I can't find a gas-phase or matrix-isolation structure of the specific substance itself. DMacks (talk) 16:20, 12 January 2021 (UTC)
Part of the issue probably lies with the most common CAS numbers. 14637-88-8 (Dy) and 12084-29-6 (Ba) resolve the structures above and appear prominently in goggle if you search for the compounds by name. There are CAS numbers for Dy-acac as a trihydrate (18716-76-2) and Ba-acac as a general hydrate (206752-34-3) but they're obscure by comparison. Chembox supports multiple CAS numbers so we could include both sets with an explanation in the body text. --Project Osprey (talk) 16:33, 12 January 2021 (UTC)
Well there's no fault for anyone, and admittedly I am picky about hydrates. Part of the problem is that these compounds are used as precursors by materials scientists, and all they really care about is that the precursor degrade to the oxides. I do think that Ba(acac)2 should be AfD'd. --Smokefoot (talk) 20:52, 12 January 2021 (UTC)
I'd support that. Many of the more esoteric examples seems to have come from one enthusiastic editor. Our usual requirements for notability should apply, otherwise it's just stamp collecting. --Project Osprey (talk) 10:17, 13 January 2021 (UTC)
I also support deleting the less notable ones (do we have consistent criteria for chemicals?). The OP asks about "how to draw the lines". I don't think that IUPAC gets in to that issue, since it usually sticks to nomenclature. For articles in Wikipedia, I think that the pseudo-3D representation is fine (assuming that the structure illustrated is in line with for example X-ray structures in sources). Note that representations in Chemspider and elsewhere often show these organometallic structures as salts with disconnected fragments. Chemical databases don't, AFAIK, allow partial bonds of the type implied by a dotted bond: they have to represent structures in conventional connection tables, and hence InChI strings. This leads to some difficult problems of representation, since the tendency is to draw one ketone in its enol(ate) form and the other as a ketone, which can lead to problems, since in practise the system is a resonance. Mike Turnbull (talk) 12:41, 13 January 2021 (UTC)
Should we delete the errant pictures? If they remain on commons then some well-meaning editor will eventually reconnect them to the articles.--Project Osprey (talk) 22:56, 20 January 2021 (UTC)
Definitely a good idea. But make sure there is a comparable correct image as replacement. Commons has a weaker standard than enwiki's WP:V/WP:NOR: "delete A because it's wrong" might be rejected by "but it's the best/only we have", whereas "delete A because B is a more correct version" is generally trivial. DMacks (talk) 23:49, 20 January 2021 (UTC)
The errant images (could you list them?) should at least be removed from all articles before requesting deletion. Incorrect and orphaned files have a good chance of being deleted. --Leyo 08:40, 2 February 2021 (UTC)
I've nominated the Ce and Dy images above for deletion. Not sure what to do about the Ba one as it's used in de:wiki and I don't know how to explain myself over there. I assume the other images are fine (@Smokefoot:)? --Project Osprey (talk) 09:52, 2 February 2021 (UTC)
I updated several of the imperfect images. The Ln(III) complexes apparently are always 8-coordinate with two aquo ligands, although many L's are possible. The Ce case is curious because a Ce(IV)(acac)4 is also known (like Zr and Hf cmpds). I left a note on German article about the 4-coordinate Ba(acac)2 being bad. The English article on Ba(acac)2 is so heavily tagged that readers will know to be wary.--Smokefoot (talk) 13:06, 2 February 2021 (UTC)

Wikipedia:Sandbox organiser

Sandbox Organiser

A place to help you organise your work

Hi all

I've been working on a tool for the past few months that you may find useful, especially if you create new articles. Wikipedia:Sandbox organiser is a set of tools to help you better organise your draft articles and other pages in your userspace. It also includes areas to keep your to do lists, bookmarks, list of tools. You can customise your sandbox organiser to add new features and sections. Once created you can access it simply by clicking the sandbox link at the top of the page. You can create and then customise your own sandbox organiser just by clicking the button on the page. All ideas for improvements and other versions would be really appreciated.

Huge thanks to PrimeHunter and NavinoEvans for their work on the technical parts, without them it wouldn't have happened.

Hope its helpful

John Cummings (talk) 11:23, 6 February 2021 (UTC)

Inconsistency in some Chemistry articles

I was doing some editing and research and came across this situation. https://en.wikipedia.org/wiki/Maleic_acid_dibutyl_ester https://en.wikipedia.org/wiki/Dimethyl_maleate Dimethyl maleate https://en.wikipedia.org/wiki/Diethyl_maleate Diethyl maleate

So Dimethyl maleate article is called that as is diethyl maleate. However, Dibutyl maleate (DBM) article redirects to Maleic acid dibutyl ester. Surely there needs to be some consistency. Probably needs a very experienced chemistry editor to look at. GRALISTAIR (talk) 17:11, 16 February 2021 (UTC)

There is probably no reliable way to fix all these issues. In principle we have the general Wikipedia guidance to use MOS:COMMON, and hence give article titles the name most commonly used. Personally I think that Dibutyl maleate would be the one to choose and hence justify a move to be consistent with the others. However, as the Chemspider entry for that compound shows, it has been referred to by over 30 synonyms! We can use redirects to help with that (although I note that DBM as a synonym is not listed as one of the disambiguation terms for dibutyl maleate). Do you have a proposal to fix this and related issues, GRALISTAIR? Mike Turnbull (talk) 17:59, 16 February 2021 (UTC)

My proposal would be to rename the Maleic acid dibutyl ester to Dibutyl maleate. (I dont think I have the permissions or skill to do that though) Once that is done I can add DBM as a synonym later. GRALISTAIR (talk) 20:27, 16 February 2021 (UTC)

Our article titles are indeed a little messy, but hey, we have redirects, which solve lots of problems. --Smokefoot (talk) 21:49, 16 February 2021 (UTC)

I have moved the page. Dibutyl maleate does sound more systematic.--Project Osprey (talk) 23:12, 16 February 2021 (UTC)

Mary Ann Mansigh

deletion discussion

Female programme writer, co-creator of moldyn method. Yo, we all need to come out for this one, especially if you're in the computational community in phy sci, bigly. Already posted on science wp's super-forum as well. Alder, Rahman and Wainwright are dead let's do this one while she still lives. Ema--or (talk) 00:09, 12 February 2021 (UTC) This one's still tight, people. If you know about Tsingou, the ENIAC Ladies, the Hidden Figures, Hamilton, and others (though not so much Hopper, she didn't really work in sci comp) then you should back Mansigh. She's a card-carrying member of that fellowship. Ema--or (talk) 03:53, 12 February 2021 (UTC)

Sorry for my non-NPOV canvas! Ema--or (talk) 21:15, 15 February 2021 (UTC)

Hi, just an issue to discuss. Just wanted to name an issue, which I asked for consultation on, but was not able to get any thing on before the end of discussion. There is the issue of my inconsistencies on Mansigh btw main space and other-space, particularly afd- and Wp project-space, although it is particularly a matter for subjective interpretation. I’d like to end by once again apologising for any trouble and thanking anyone who offered any opinion or contribution to the chat, as well as for the space and audience in a place such as this. Bye, until the next time. Ema--or (talk) 18:31, 18 February 2021 (UTC)

FKM

The article FKM could use some work. I already did a cleanup pass on it, but it needs attention from an expert. For now, it does not really provide any information about the properties of the substance that make it suitable for the claimed applications, and it relies almost entirely on low-quality primary-source materials from manufacturers/vendors (and may be over-dwelling on them and their brand names in the lead).  — SMcCandlish ☏ ¢ 😼  14:27, 5 March 2021 (UTC)

PS: See also Talk:FKM#Merge from Viton (about getting rid of a spammy WP:POVFORK).  — SMcCandlish ☏ ¢ 😼  14:38, 5 March 2021 (UTC)

Noticeboard discussion on reliability of MDPI journals

There is a noticeboard discussion on the reliability of MDPI journals. If you are interested, please participate at Wikipedia:Reliable sources/Noticeboard § MDPI journals. — Newslinger talk 13:29, 8 February 2021 (UTC)

There is nothing about MDPI on the page pointed to, although there is discussion in the (non-editable) archives. How and where do I add a comment? Do I re-open the discussion with a new title on the current page - although this would seem to break the thread. Petermr (talk) 16:12, 15 March 2021 (UTC)
The discussion seems to have been archived although no consensus was reached, as far as I can see. The archive is WP:Reliable_sources/Noticeboard/Archive_329#MDPI_journals and I guess you could re-activate it if you have opinions, Petermr. Mike Turnbull (talk) 18:05, 15 March 2021 (UTC)

Chemical data pages - move to Wikidata?

I recently became aware of the "data pages" located in Category:Chemical data pages and Category:Chemical element data pages - containing numerical information relating to various elements and compounds. These were all created long before Wikidata was a thing, and it's been brought up several times before that these types of pages probably aren't suitable for Wikipedia itself. (in 2007, 2015, 2016, and 2019) In the 2015 discussion, a couple of users objected to using Wikidata on the basis that it wasn't quite suitable for there at the time either due to technical limitations. As far as I can tell this is now a moot point, as all of the data included on these pages should fit into the site's current data structure without too much hassle (correct me if I'm wrong). Since it's been about four years since this issue was last brought up on this specific talk page, I wanted to know if there are still any objections to migrating this info to Wikidata. Would it be easiest to accomplish this by parsing the pages with a bot? Ionmars10 (talk) 05:16, 31 January 2021 (UTC)

The information is probably too diverse for a bot. Wikidata may need more things created on a case by case basis to absorb this info. I see quite a bit that should be added to the chembox of the main article (eg Aluminium chloride (data page) could be fully merged), or could be in the main article, eg bond-lengths. Some might be moveable to a more specific page, eg solubility of xyz, or spectrum of acetaldehyde. Graeme Bartlett (talk) 23:57, 2 February 2021 (UTC)
I agree that some of the Category:Chemical data pages could be removed - namely those consisting of blank (or almost blank) tables which haven't been populated in 15-16 years (e.g. Valine (data page), Hydrogen iodide (data page)). I don't expect they'll ever be filled in, so we may as well merge them in to the main articles. Other pages, like Water (data page) I think should be left, merging to main-page is impossible but it's also probably a challenge for wikidata. Category:Chemical element data pages are different, I think they should be left as they are. --Project Osprey (talk) 10:38, 3 February 2021 (UTC)
Chembox checks if a page is named "pagename (data page)" and then links to it with the link "Supplementary data page". I guess nobody sees it... See Aluminium chloride for the link Christian75 (talk) 21:09, 26 March 2021 (UTC)

Discussion at Jabir ibn Hayyan

There is a discussion at Jabir ibn Hayyan about whether to include the title "father of early chemistry". Members of this WikiProject are kindly invited to express their opinion. Apaugasma (talk|contribs) 13:40, 27 March 2021 (UTC)

Chemical Markup support for files

Hi. We have had a project in mediawiki to allow chemical markup support for Wikimedia (let .mol, .rxn files to be uploaded and shown in Wikipedia). Some links: phab:T18491, mw:Extension:MolHandler, mw:Chemical Markup support for Wikimedia Commons. I would like to revive/finish the project or decline it. First I want to know if this is something that you would find useful. Is svg enough? I don't think we can deploy Jmol support as the extension needs lots of work but MolHandler would be rather straightforward. Is there a way to massively produce and upload these files in Commons if the support is added? Ladsgroupoverleg 14:00, 27 March 2021 (UTC)

The huge advantage of .mol files is that chemical drawing software can take them as input so that they can be used as starting points for new drawings. svg files are hopeless in this regard, limiting their re-use to simple things such as altering some text. However, I appreciate that for general use as browser-supported zoomable images, svg will always have the Edge (pun intended). Molfiles were originally developed by MDL Information Systems back in the 1980s but are now public domain. Any record in Chemspider which can be represented by a connection table can be downloaded from that website as a .mol file. Dassault Systèmes who are the descendants of MDL still keep their .skc file format (for chemical reactions, sketches and more in what I suppose to be a vector graphic-type format) proprietary and .rxn files are a sort of half-way-house between .mol and .skc since they are specifically designed to encode reactions of the type A -> B. So, I would strongly support having Wikimedia focus on .mol files and ignore .rxn ones. If you could persuade Dassault Systèmes to give you a viewer for .skc files, so much the better but I doubt you'll get a licence for that. Whether Commons should attempt a bulk upload of .molfiles from Chemspider's API or elsewhere is another matter. Mike Turnbull (talk) 16:26, 27 March 2021 (UTC)
(Disclaimer, as author). Molfiles and InChI work when there is a clear covalent connection table and are very widely used in pharma and related industries. However they are not easily extensible and start to fail for inorganics, nanomaterials, polymers, composites, mixtures, etc. Many years ago Henry_Rzepa and I created Chemical_Markup_Language which, being XML, is extensible and semantic and which can manage 2D and 3D coordinates simultaneously as well as SVG. It's therefore an adaptable container for well-defined chemical objects. With the development of chemistry in Wikidata, many more complex concepts can be developed through annotation of XML elements. Being XML it can be transformed into other molecular formats. (See also next topic). Petermr (talk) 17:18, 29 March 2021 (UTC)

Wikidata support for solutions

I am starting to use Wikidata to annotate published chemistry semantically, concentrating on synthesis. A common concept is concentration of solutions as in: 

100 mL of 6M HCl


This comprises several concepts:

  • quantity
  • volume
  • concentration (molarity) + number
  • mixture (in this case HCl and water)

Has anyone used Wikidata to model this? It's quite complex in RDF and it may be useful to have specific Qitems or Properties which are required by scheme. And, more generally , is Wikidata able to model relationships other than naked triples? Petermr (talk) 17:29, 29 March 2021 (UTC)

CAS Common Chemistry greatly expanded

(Also posted in WT:Chemicals) Chemical Abstracts Service just made this official announcement: CAS Common Chemistry has now been expanded from the original 7800 to almost half a million substances, and new content added. This puts far more CAS Registry Numbers into open use, and the site itself is now listed as having a CC BY-NC 4.0 license. Previously the pages was mainly names, structure and Wikipedia links; the new version now includes some basic physical properties such as MP, BP, density. Some of you may recall the discussion last year on choosing the "top million substances"] - this was in fact part of this project, but we needed to keep the source of the project under wraps at the time - but it helped us define the substances that matter. I hope Wikipedians appreciate the value of CAS working in the open domain much more than we saw previously.

The long-term plan is to refine the site as time/code allows, and both Wikipedia and Wikidata links will be added once we've figured out all the matches. Links from Wikipedia to CAS do seem to work, and I think that's true even for substances not previously in Common Chemistry. Egon Willighagen is coordinating this project and the cross linking in Wikidata. Walkerma (talk) 19:49, 17 March 2021 (UTC)

This is fantastic news. Thanks Walkerma and Egon Willighagen for making this possible. In this discussion, it was proposed to use CAS numbers for authority control for drug substances. Before this latest announcement, this proposal was a complete non starter, since CAS had not made public CAS numbers for many drugs. In their official announcement, CAS states that CAS numbers will be made public for compounds on regulatory lists. I assume that this expanded list would then at a minimum include all FDA approved drugs. Even better would be for make public CAS ids for the approximately 8000 Wikipedia. drug articles. Has this been done? If so, it might then make sense to use CAS numbers as authority control for drugs. Boghog (talk) 20:36, 17 March 2021 (UTC)
Boghog, if you have a list of the 8000 CAS numbers, I can check them tomorrow. --Egon Willighagen (talk) 21:05, 2 April 2021 (UTC)
Great news, and thanks to everyone who has and is working on it! This limits Boghog's search to those that don't already have CASNo listed in the article. DMacks (talk) 21:04, 17 March 2021 (UTC)
Thanks DMacks for the link. Many CAS numbers were added to drug articles without consulting CAS Common Chemistry. The critical question is how many of these Wikipedia drug CAS numbers have working links to CAS Common Chemistry which would be a prerequisite for using CAS numbers as authority control identifiers. Boghog (talk) 21:31, 17 March 2021 (UTC)
Two excellent and separate issues here. Would be trivial to pull a [wikipage]:[infobox-casno] table from a set of articles that can be described in terms of a certain infobox detail or category or link to/from another article or... DMacks (talk) 23:49, 17 March 2021 (UTC)
We should be doing a cross check at some point, to see the variants. Graeme Bartlett (talk) 01:04, 18 March 2021 (UTC)
For the drug articles missing CASNos, I cannot find any on the new list so far. Most of these articles are new and are for experimental or recreational drug variants. Some are complex mixtures, eg vaccines. Graeme Bartlett (talk) 01:04, 18 March 2021 (UTC)
OK after 20 I found one for 4-Methylthioamphetamine. Graeme Bartlett (talk) 02:44, 18 March 2021 (UTC)
Egon is planning to run a validation script in Wikidata to match substances there with CAS numbers. Would that be helpful in finding the right matches? If their site is missing significant registry numbers, CAS may be open to adding more substances if we can demonstrate they are important medical drugs and not just experimental or obscure recreational drugs. Walkerma (talk) 03:17, 18 March 2021 (UTC)
I just reported on the first results on this page. The list of CAS numbers validated in Wikidata is found at https://w.wiki/39oN This query uses the reference info added by the validation script. --Egon Willighagen (talk) 21:05, 2 April 2021 (UTC)
Thanks for the suggestion, but I don't think it would narrow down the list enough. We would also need some indication that the drug is approved for use in at least one country. As far as I can tell, this information is not stored in Wikidata. I don't have time for this at the moment, but I plan to write a script that would look for articles containing {{Infobox drug}} templates with with non-blank legal status fields that would also return the CAS number and then query Common Chemistry with those CAS numbers. I think in addition to approved drugs, illicit drugs that are on government regulatory lists are also fair game. Boghog (talk) 09:03, 18 March 2021 (UTC)
One highly relevant drug list to check would be Category:World Health Organization essential medicines which currently has 474 members. Boghog (talk) 11:23, 18 March 2021 (UTC)
That is indeed good news. As well as providing links could this be used to validate our CAS No's? While there has been some work with databases in the past I expect most of our CAS No's have been added manually over many thousands of edits by dozens of editors using a variety of sources. It would be interesting to see if there are any disagreements (are we using any old deprecated numbers?). I expect we'd need access to the backend list to do that though? --Project Osprey (talk) 09:40, 18 March 2021 (UTC)
Update - Pubchem has now added links to all the CAS Common Chemistry pages, as well as a nice "Related CAS" section that includes links, as in this example. That may help us in getting matches aligned properly. Walkerma (talk) 14:22, 18 March 2021 (UTC)
Well done, Walkerma and Egonw. The CAS site is broken today so I can't investigate some of the thoughts I had about it when I looked yesterday. It seems to provide a sort of "infocard" for the compounds, with InChI key etc that would be the obvious way to confirm that the relationships to Wikidata and hence Chemboxes are correct. I wondered if CAS were going to provide a API to scrape their data like other databases do. I was a little disappointed that they don't seem to offer more information than can be obtained elsewhere (e.g. Chemspider, which as CAS now does, offers the chance to download a .mol file for a chemical). I hoped they might provide, for example, a citation to the first (i.e. earliest) reference known for a given CAS number, which would help immensely in writing Wikipedia articles. More thoughts later! Mike Turnbull (talk) 11:54, 19 March 2021 (UTC)
After checking many more articles missing CAS numbers I found many more RNs, even for calamine lotion, but rather than drugs, the best results from this collection are for the other molecular compounds and ions. Graeme Bartlett (talk) 11:33, 20 March 2021 (UTC)
One useful feature of the new release is that it gives "deleted or replaced" CAS numbers for a given hit. When used as queries, these outdated CAS numbers redirect to the correct current CAS number. This means that any Wikipedia article using a now-defunct identifier will still link correctly if it is in the 500,000. I also discovered that anyone can ask for API access "using this form".. I don't know what criteria they use for granting access. Mike Turnbull (talk) 11:55, 20 March 2021 (UTC)
It might anyway be good to identify deleted or even invalid CAS numbers. --Leyo 20:41, 26 March 2021 (UTC)

CAS Common Chemistry hydrogen problem

For oxy salts, the CAS Common Chemistry entries have errors in structure. eg https://commonchemistry.cas.org/detail?ref=7778-80-5 for potassium sulfate indicates the material is a mixture of potassium metal and sulfuric acid, with a SMILES and inchi that support that idea. This means that the structure / SMILES / INCHI will not match what we have in our articles. What is CAS up to? For halides like NaCl https://commonchemistry.cas.org/detail?ref=7647-14-5 they are matching. Graeme Bartlett (talk) 22:39, 31 March 2021 (UTC)

The problem will be in their data model. Note that NaCl is only "correct" because they show it as a covalently bound Na-Cl. Likewise they could have used K-O(SO)2O-K for potassium sulfate and hence achieved a better result (indeed, that version may well have a different CAS number). Neither of these examples are fully "correct", given that most chemists want to see both materials as ionic, not covalent. I am aware from literally hours and hours of discussion with colleagues and IT specialists that representing organic or inorganic salts in a chemical substance database means making certain compromises, according to the purposes and priorities you want to achieve. Mike Turnbull (talk) 11:42, 1 April 2021 (UTC)

Chemistry World role

I wouldn't normally post this sort of thing here, but for those in the UK there's an internship going as a science writer at RSC's chemistry world. I would think that the overlap in skills with a chemistry wikipedian would be significant. Closing date is Monday. --Project Osprey (talk) 07:43, 10 April 2021 (UTC)

Wikipedia - Wikidata mismatches?

So, everyone who started looking at the missing CAS RNs will immediately recognize some patterns. One pattern is that sitelinks between Wikipedia and Wikidata are not always correct. Wikipedia may be more stereo-specific, or less. There are multiple solutions to solve this: 1. make the least stereospecific page more specific, 2. make a new Wikidata page to match the English Wikipedia (and make the appropriate links), 3. accept as is. And probably a few more. The Wikipathways teams has solved a number of these kind of issues over the years. What do the two WikiProject Chemistry teams think the best course of action is? Cross-post: https://www.wikidata.org/wiki/Wikidata_talk:WikiProject_Chemistry#Wikipedia_-_Wikidata_mismatches? --Egon Willighagen (talk) 11:45, 10 April 2021 (UTC)

Coverage of solid-state chemistry

Hey all, been perusing a number of pages related to solid state chemistry/condensed matter physics and finding a number of issues. Curious if there's a taskforce or anything specifically dedicated to these pages. Thanks! -- 2ReinreB2 (talk) 16:15, 12 April 2021 (UTC)

Not really - but you can raise issues here. --Project Osprey (talk) 15:13, 13 April 2021 (UTC)
@2ReinreB2: If you have identified major topics that are under-developed - and there are many - then dedicate your editing energies to very general themes with an emphasis on textbook-based content (e.g. Kittel's book on SS Physics). Too often, it seems, when an editor claims to rectify an under-reported area, what they really aim to do is write about something specialized and/or promote work by themselves or their pals. Happy editing. --Smokefoot (talk) 17:05, 13 April 2021 (UTC)

Steady-state approximation

Hi, I am new on Wikipedia, so please forgive me if don't do things right. I notice that there was no page about the quasi-steady-state approximation and the partial-equilibrium approximation, which are among the basics of chemical kinetics. I wrote an article about them which is waiting review: https://en.wikipedia.org/wiki/Draft:Quasi-steady-state_approximation_and_partial-equilibrium_approximation_(Chemistry) Maybe someone on the chemistry community could review this article ? Agnespt (talk) 15:08, 13 April 2021 (UTC)

@Agnespt: Looks pretty hairy to me! Many of us editors occassionally write hyper-specialized articles because we are nerdy and have pet topics, but we mainly aim for general, digestable themes. A hallmark of general themes is that almost all refs are to textbooks or major reviews. Another guideline about which we editors are cognizant: WP:NOTTEXTBOOK. We editors are presenting facts, not explaining them. Finally, under what Wikipedia is not is this quote "A Wikipedia article should not be presented on the assumption that the reader is well-versed in the topic's field. Happy editing. --Smokefoot (talk) 17:19, 13 April 2021 (UTC)

Introductory Organic Chemistry

This page has that student-project look about it:

It seems to be about topics that one would find in a course (alkanes, alkenes, ...) rather than about the course itself (when schools started offering it, what the standard books are, etc.). XOR'easter (talk) 20:47, 19 April 2021 (UTC)

I draftified it while you were posting this message, then my edit here edit-conflicted:) That article was definitely not ready for mainspace. I'm pretty sure it's a course at MIT and that it is not registered with wiki-edu. 21:10, 19 April 2021 (UTC) — Preceding unsigned comment added by DMacks (talk • contribs)
Ah, there it is. Thanks! XOR'easter (talk) 21:28, 19 April 2021 (UTC)

Redox vs. Oxygen Reduction Reaction (ORR)

Even though I got A's on all 4 chem courses I took back in college, definitely not my forte. The second article, Oxygen Reduction Reaction (ORR) was recently created. When I went to move it to Oxygen reduction reaction as per naming conventions, was informed a redirect already existed, pointing to Redox. Are these two similar, but different processes? Or is the new article simply about the existing article? Thanks for any help. Onel5969 TT me 14:37, 28 April 2021 (UTC)

IMO, Oxygen Reduction Reaction (ORR) should have been created in draft space, and in the current shape it is in, I would think that it should be moved there first. As I understand it, an oxygen reduction reaction is a redox reaction in which the oxidizing agent is O
2, i.e., these are a specific subset of redox reactions. As such, it could either belong as a section of the Redox article or could be a separate article referenced by a section in that article, once its shape is coherent enough (e.g. as a start class article). At the moment it looks too much like notes from a class project on a particular application. —Quondum 15:43, 28 April 2021 (UTC)
I agree that the current Oxygen Reduction Reaction (ORR) is not ready for mainspace. It appears to be styled as a school essay on some fuel-cell aspect but written as if it's a broader-scope on a parent topic. The intro to the new page does correctly note that an oxygen reduction reaction is just a redox reaction where oxygen is the chemical getting reduced. I don't see notability for this specific variant as a general topic. The new aricle only seems to be about a the fuel-cells application of that variant, which could potentially be a notable intersection of parent topics. DMacks (talk) 16:04, 28 April 2021 (UTC)
@Catbathat: DMacks hit the nail on the head: "not ready for mainspace". Its an important topic, because it is the half reaction of many fuel cells. The original author, a student who was forced to write this thing, has distorted the article with a focus on "M-N4 and its derivatives ORR electrocatalyst", which is verging on ridiculous (no one is using coordination complexes! it all about alloys). The article is yet another example of the fluff that sometimes comes from courses where teachers assign essays but are not smart or energetic enough to edit their students' work. So we get handed a bag of crap to clean up. Its a very big area of research/technology. Cytochrome c is the bio-part of the ORR, our respiratory existence depends on it, I think.--Smokefoot (talk) 17:43, 28 April 2021 (UTC)
The oxygen half-cell reaction is important, but is it an article-worthy topic? We don't (to my knowledge) have articles on any other half-cell reactions. Realistically, how much could be said without becoming very esoteric? (I don't meant that rhetorically) - it feels like a content-fork for a fuel cell article. Electro-chemistry baffles me though, so maybe don't pay me any heed. --Project Osprey (talk) 18:28, 28 April 2021 (UTC)

Folks, thank you very much for the detailed input. I've moved the article to the draftspace, with a note for the student to reference this discussion to see what the issues are. Again, thanks. Onel5969 TT me 00:58, 29 April 2021 (UTC)

@Smokefoot: sounds like the course will have multiple pages of interest (or headache, depending on how it goes) for you: and their other currently-listed ones are all existing articles: Zintl phase, Borate, Metal-metal bond, Terphenyl. DMacks (talk) 02:17, 29 April 2021 (UTC)

I don't mean to sound rude, but...

There are several scientific findings listed in timeline of physical chemistry that have next-to-nil relevance to physical chemistry, or even chemistry as a whole. Einstein's theory of relativity? Newton's classical mechanics? Particle physics? What do these stuff have to do with chemistry? Why are you chemists so obsessed with claiming milestones from other sciences to chemistry? Why are you pretending that stuff pertaining to physics belong to chemistry now? --190.124.30.42 (talk) 08:58, 29 April 2021 (UTC)

For a start in an important area of chemistry, which is likely to expand, Einstein's theory of relativity seriously affects the properties of heavy elements and their compounds. Physical chemists also have to understand classical mechanics. Particle physics might be less important, but I guess some chemists have to know at least something about it. --Bduke (talk) 09:19, 29 April 2021 (UTC)
I mean, I know there are branches of physics that are closely interwined with chemistry, namely thermodynamics, electromagnetism and quantum mechanics. But the only thing from classical mechanics that carries over to chemistry is the conservation of energy and the concept of speed or rate (chemical kinetics). By themselves, the laws of Newton are extremely distanced from what you study in chemiatry. Do Newton's second law play any sort of role in explaining chemical reactions? Because I'm pretty sure that only quantum mechanics can be applied in them. As for relativity, that feels like an overly specific application that doesn't compare to the case of the aforementioned areas of physics; if it's nonetheless relevant, then the timeline article should at least make a brief mention of importance in studying chemical elements, because by itself the phenomenology of relativity is strictly physical instead of chemical. And I still don't understand what part of particle physics is necessary, because the majority of chemical processes occur at an atomic-to-molecular scale. Once again, I don't mean to sound confrontational, and I apologize in advance if thse posts read like I come off as such, but it's pretty odd to see the physical chemistry template as it is now -- it looks almost like a copy-and-paste draft from timeline of physics, only mixed with struff from actual physical chemistry. I feel like the timeline article should only include events that are closely relevant to the subject of physicial chemistry. I don't recall timeline of physics borrowing anything from chemistry-related milestones (and for the record, it doesn't obsess with citing almost every single discovery from mathematics either, despite the extensive application of math to physics), so why is the other way around OK? To cite another example, timeline of biology and organic chemistry limits itself to discoveries and findings in those mentioned areas, as there is very litle from inorganic chemistry or radiochemistry that is of use there and thus isn't mentioned.
I admit I'm in the minority here, because the current state of the physical chemistry timeline page has been around for, likely, forever. But I don't think it's fair to cite stuff from physics that only have an extremely perfunctory connection to chemistry. Nevertheless, I don't plan to argue about this forever, because I have the somber feeling that I'm just supporting a lost cause (especially here which is the heart of chemistry-based articles). --190.124.30.42 (talk) 17:07, 29 April 2021 (UTC)
The list does seem to be short on discoveries relating directly to physical chemistry and long on discoveries that are only tangentially related. I'm sure the list in the timeline would benefit from an extensive reworking. As with most of these things, it would need someone who wants to actually do it. —Quondum 19:24, 29 April 2021 (UTC)

Category: chemical suffixes

I'm still quite new here, and I'm not so sure this is supposed to go here, but I would just like to bring up that the category: chemical suffixes seems to be missing a few suffixes. Maybe this is because of not having a few pages published? I'm not so sure if -ate and -ide are supposed to be there, but just bringing this up for further discussion. Lelojello (talk) 02:18, 3 May 2021 (UTC)

For much of these with nothing much to say, Wiktionary may be better wikt:-ate, wikt:-ide Graeme Bartlett (talk) 07:48, 3 May 2021 (UTC)

Referencing for chemistry examples at Group (mathematics)

Over at Group (mathematics), we're doing a Featured Article Review, most of which has come down to clarifying phrasings here and there and supplying references where necessary to bring it up to modern standards. Some of the examples in the "Symmetry groups" section are about molecular symmetry, so they might be of relevance to the community here. Given the nature of the article, most things in it can be found in many references; the challenge is picking among them for particularly clear, insightful or classic ones. XOR'easter (talk) 03:41, 4 May 2021 (UTC)

List of quantum chemistry and solid-state physics software

There is a conflict at List of quantum chemistry and solid-state physics software about what to include in this list. Wikipedia:Stand-alone lists suggests that a selection criterion of "being notable/having its own article" is valid. Unfortunately someone else disagrees and keeps restoring the full list including many red links. The discussion is going nowhere so more eyes are needed at Talk:List_of_quantum_chemistry_and_solid-state_physics_software#Notable. Thanks in advance. The Banner talk 14:11, 4 May 2021 (UTC)

144 articles without a CAS RN but with one in the CAS Common Chemistry database

According to this PetScan search, there are currently 144 articles without a CAS RN in the chembox or drugbox, but with one in the CAS Common Chemistry database (as referenced on Wikidata). I would appreciate to get some help for checking the CAS RNs and to add them locally. Using {{subst:#invoke:Wikidata|claim|P231}} allows to do this task quicker, but the CAS RNs still need to be checked before adding. --Leyo 00:16, 6 May 2021 (UTC)

I've added the first 20 and will continue to work my way through as time allows. I couldn't find one for Atomic carbon. Isavuconazonium had a CAS number added on 7th Jan... is this an old list? There appear to be issues with the infoboxes of SB-649868 and Emedastine, namely a lack of sectioning. --Project Osprey (talk) 11:29, 6 May 2021 (UTC)
Happy to help: I'll start at the bottom of the list, assuming that Project Osprey is working from the top. I guess that the best way to proceed if there are any issues with individual articles is to move on, so a re-do of the search on PetScan will highlight them later. I'm checking that the CAS number "invoked" matches on InChI key, which seems like a robust way of doing things. Mike Turnbull (talk) 11:45, 6 May 2021 (UTC)
I think we are  Done Project Osprey! No problems in the ones I did and the magic #invoke made it very easy, Leyo Mike Turnbull (talk) 17:12, 6 May 2021 (UTC)
Thanks to everyone who contributed!
What are the reasons why 6834-98-6 for Pentamycin have been left out? They seem to be correct to me on the first sight.
@Egon Willighagen: You might want to update Wikipedia talk:WikiProject Chemistry/CAS validation/CASCommons to reflect these additions. --Leyo 20:24, 6 May 2021 (UTC)
Check. I will run the scripts this weekend. (Fighting project reporting today...) --Egon Willighagen (talk) 09:44, 7 May 2021 (UTC)
I've checked both Pentamycin and atomic carbon and updated them now, as they were indeed correct, Leyo, so the search above now gives no hits. Mike Turnbull (talk) 11:17, 7 May 2021 (UTC)

Help request with a citation

For the article on groups, I am looking for a citation backing up "Hexaaquacopper(II) complex ion, [Cu(OH2)6]2+. Compared to a perfectly symmetrical shape, the molecule is vertically dilated by about 22% (Jahn–Teller effect). ". Looking at Jahn-Teller effect, this is pretty much what is stated there, but I'm not sure whether the references given there support this precisely (I'm a mathematician and have only little background in chemistry). Can someone knowledgeable about this help out in pointing me towards a precise reference that matches this claim? Thanks! Jakob.scholbach (talk) 18:02, 7 May 2021 (UTC)

The Cambridge Crystallographic Database (CSD) lists 106 structures of [Cu(OH2)6]2+ salts, and there are still more not in the database. If I were a better man, I would be able to produce a histogram of the Cu-O distances. Ben Mills might be able to do that.
One proviso is that the anions interact with the O-H groups. Also, aqua complexes never have a "perfectly symmetrical shape" because water is bent and bound water is usually pyramidal.
  • for CSD code ZUCYUT . doi:10.3998/ark.5550190.p008.911. {{cite journal}}: Cite journal requires |journal= (help); Missing or empty |title= (help), four Cu-O distances at 202.5 pm and two (mutually trans) are at 218.3 pm.
  • for comparison, I checked hexaammine complex CSD code OLELEW . doi:10.1021/cg034071w. {{cite journal}}: Cite journal requires |journal= (help); Missing or empty |title= (help) for [Cu(NH3)6]2+ (with complicated anion), the effects are reversed: four Cu-N bonds = 215 and two (mutually trans) are at 205. The Jahn-Teller distortion can go either way.--Smokefoot (talk) 19:00, 7 May 2021 (UTC)
OK, if I understand you correctly (?) this statement is not as straight as it seems (in the sense that the actual effect depends on further circumstances). Is there a more unambiguous example of the Jahn-Teller effect that we could use as an unquestionable example in the group article? Thanks a lot! Jakob.scholbach (talk) 18:01, 8 May 2021 (UTC)
These examples I provided are legit and about as unquestionable as you will get. In chemistry, there is no God that whispers to us that "this bond distortion 100% due to J-T effect." We are always walking on ice of varying thicknesses. So take these examples!--Smokefoot (talk) 21:14, 8 May 2021 (UTC)

This ScienceDirect summary has lots of useful content. Every textbook or review I've read on the Jahn-Teller effect uses [Cu(OH2)6]2+ as the main example. --Ben (talk) 18:24, 8 May 2021 (UTC)

Thanks, Benjah-bmm27 and Smokefoot, for your help. I have removed (in the group article) the assertion about the precise %-age of the distortion. Jakob.scholbach (talk) 12:52, 9 May 2021 (UTC)

Category:Science articles needing expert attention

You are invited to participate in a discussion Wikipedia_talk:WikiProject_Science#Category:Science_articles_needing_expert_attention about the following articles:

–LaundryPizza03 (dc̄) 14:31, 12 May 2021 (UTC)

Key intermediates

"Key intermediate" sounds good, and I confess to using that cliche. But aren't intermediates automatically "key"? I was going to remove the adjective key" in many articles, but I just wanted to hear possible alternative views. Similarly for "key enzymes". In essence, when we say that something is key, what we are usually saying is that its one of my pets.--Smokefoot (talk) 20:24, 23 May 2021 (UTC)

I think it's a fairly common diction, even in the literature. I agree that it's superfluous but does it enhance readability or help clarify notability? I can't see anyone getting confused by the lack of 'non-key intermediates'. --Project Osprey (talk) 09:16, 24 May 2021 (UTC)
I agree that it is a cliché that, if it means anything, is shorthand for "a compound we fully characterised en-route to the real target of the work" (as distinct from one that we used without full purification and characterisation). There are certainly a lot of articles that use these words without any real justification, as this search shows [1]. I'm not sure I could be bothered to remove the "key"s, though — there are too many other ways articles could be improved to make this one a priority, in my opinion. Mike Turnbull (talk) 10:09, 24 May 2021 (UTC)
Thanks for the feedback. I agree that it is a small matter and kind of a cultural thing. The part that bugs me is the implication that other intermediates/enzymes are not key.--Smokefoot (talk) 12:51, 24 May 2021 (UTC)
To be honest, I don't think that anyone is going to revert you if you change them. --Project Osprey (talk) 14:09, 24 May 2021 (UTC)

Most viewed stub in this Wikiproject

Material 11,298 376 Stub--Coin945 (talk) 14:09, 30 May 2021 (UTC)

I have rated this to start, SO what was the second? @Coin945: Graeme Bartlett (talk) 22:38, 30 May 2021 (UTC)

Two other stubs:

And a few starts:

--Coin945 (talk) 22:42, 30 May 2021 (UTC)

Fischer carbene

I have accepted this article from draft after giving it some formatting improvement, and without any detailed research of the accuracy of the chemistry. I think that any improvement should be done in article space rather than draft space. Robert McClenon (talk) 15:34, 31 May 2021 (UTC)

You might ask around. For example, get the submitting author to submit better artwork. And then there is this little thing called WP:SECONDARY, the student is doing some serious cherry picking. But thanks for the heads up.--Smokefoot (talk) 16:03, 31 May 2021 (UTC)
The article is a pretty good first draft (I fixed one bare doi): Smokefoot has correctly commented on its reliance on primary sources but at least there are lots of them. Actually, I'm surprised we didn't already have an article on this important subset of carbenes. The latter article mentions this type but is much less comprehensive. I agree that it should remain in Main Space. Mike Turnbull (talk) 16:12, 31 May 2021 (UTC)
According to ChemAbs, 952 articles on Fischer carbenes. Now that this junker was accepted so gleefully, Wikipedia is stuck with this student essay for a long time. 70 reviews have been written on the topic... --Smokefoot (talk) 16:17, 31 May 2021 (UTC)
With that number of reviews, it is all the more surprising we didn't previously have such an article. Can you suggest which ones would be the best to include — and what to trim away, Smokefoot? I'll comment on the originator's Talk Page that all the diagrams are .jpg rather than .svg, which is certainly a pity. Assuming they have the originals in the native format from a chemical drawing package, this could be fixed. Mike Turnbull (talk) 16:26, 31 May 2021 (UTC)
Yes, its a big topic (Fischer shared a Nobel). The article illustrates the results of an unsupervised student who focus on primary literature and factoids. In some ways the contribution is welcome but in some ways, the elaborate content complicates things. I'll shut up, and try to help out vs whinging so much.--Smokefoot (talk) 16:55, 31 May 2021 (UTC)

Case study: pyridine

Yesterday, I deleted a lot of "safety" material about pyridine. I figured that most of my edit would be reverted. But the exchange between me and Leyo illuminates some useful issues. There is a lot of generic info available on popular chemicals, so merely having a citation does not qualify a factoid for inclusion. In the case of pyridine, about 30 publications appear daily, according to Chem Abs. At risk of flooding this talk page, here are some edits that I think could be deleted AND improve the article by making it more concise and less biased.

(1) "Pyridine has a flash point of 17 °C and is, therefore, highly flammable. Its ignition temperature is 550 °C, and mixtures of 1.7–10.6 vol% of pyridine with air are explosive. The thermal modification of pyridine starts above 490 °C, resulting in bipyridine (mainly 2,2'-bipyridine and to a lesser extent 2,3'-bipyridine and 2,4'-bipyridine), nitrogen oxides, and carbon monoxide.[1] Pyridine easily dissolves in water and harms both animals and plants in aquatic systems.[2] The permitted maximum allowable concentration of pyridine was 15–30 parts per million (ppm, or 15–30 mg·m−3 in air) in most countries in the 1990s,[3] but was reduced to 5 ppm in the 2000s.[4] For comparison, indoor air contaminated with tobacco smoke may contain up to 16 µg·m−3 of pyridine, and one cigarette contains 21–32 µg.[3]"

  • The flash pt is in the chem box.
  • yes, when N-organics burn, all sorts of stuff is formed. So should we list combustion products in every organic article?
  • We - Chem editors - have already resolved not to list cigarette smoke constituents on each compound pages. Some fanatic had wanted to do this.

(2) "Pyridine is harmful if inhaled, swallowed or absorbed through the skin.[5] "

  • name something that isn't? (the advice is for a 100kg person is to avoid drinking several milliliters of this stuff)

(3) "Effects of acute pyridine intoxication include dizziness, headache, lack of coordination, nausea, salivation, and loss of appetite. They may progress into abdominal pain, pulmonary congestion and unconsciousness.[6]"

  • I thought that we agreed that Wikipedia does not compete with MSDS. These symptoms are generic and this stuff is barely toxic.

(4) "The lowest known lethal dose (LDLo) for the ingestion of pyridine in humans is 500 mg·kg−1. In high doses, pyridine has a narcotic effect and its vapor concentrations of above 3600 ppm pose a health risk.[7] The oral LD50 in rats is 891 mg·kg−1."

  • 0.5 g/kg is very, very low. See WP:UNDUE.

(5) "Pyridine is flammable."

  • Its an organic compound, 99.99% or which are flammable. Should we add that comment to every article on organic compounds?

(6) "Evaluations as a possible carcinogenic agent showed that there is inadequate evidence in humans for the carcinogenicity of pyridine, although there is limited evidence of carcinogenic effects on animals.[6] Available data indicate that "exposure to pyridine in drinking-water led to reduction of sperm motility at all dose levels in mice and increased estrous cycle length at the highest dose level in rats".[6]"

  • Here the author is witch-hunting. Limited evidence for carcinogenicity, but the author just will not relent

(7) "Pyridine might also have minor neurotoxic, genotoxic, and clastogenic effects.[1][3][8]"

  • might? really?

(8) "Minor amounts of pyridine are released into environment from some industrial processes such as steel manufacture,[9] processing of oil shale, coal gasification, coking plants and incinerators.[3] The atmosphere at oil shale processing plants can contain pyridine concentrations of up to 13 µg·m−3,[10] and 53 µg·m−3 levels were measured in the groundwater in the vicinity of a coal gasification plant.[11] According to a study by the US National Institute for Occupational Safety and Health, about 43,000 Americans work in contact with pyridine.[12]"

  • So we want Wiki-chem articles to list minor amounts released for every (nontoxic) chemical??

--Smokefoot (talk) 13:23, 5 May 2021 (UTC)

I did not say that every single piece of information of hazard/health related information should be kept. However, a ~90% clear-cut of a how section to two short sentences is certainly not an improvement.
Most of the references in that section are not individual research publications or so, but reviews or assessments such as by IARC, OSHA or NIOSH.
Would you like to get comments on your individual points listed here? If so, it might be easier to number them. --Leyo 14:45, 5 May 2021 (UTC)
I would number these sections, but my view is that they should all be dropped:
    • the content is misleading. One's going to find some evidence for "carcinogenicity/eurotoxin/etc" if dozens of papers appear daily, right?
    • superfluous: in chembox (flash pt)
    • encourages bad editing or puffing up (do we really want every organo N compound to list posssible carcinogenicity or combustion products?)
    • diminishes the truth: pyridine is essentially nontoxic (at my weight, I need to drink several grams to keel over?).
    • trivializes the real dangers. If all this bad news is about something as weakly toxic as pyridine, what about authentically dangerous stuff?
    • much of the content does not conform with our consensus-driven rules/decisions as described in our MOS (dont compete with MSDS) and, in terms of cigarette smoke, on these pages.
In any case, thank you for allowing me to express concerns. This "clear-cutting" recommendation is not made lightly, but I would settle for pruning.--Smokefoot (talk) 17:11, 6 May 2021 (UTC)
That's not what I meant with "to number". I now did so myself. I can't address all of them due to the lack of time:
(1) I agree that there is no need to repeat every single piece of information of the chembox in the text. However, relevant information could and should be discussed in the text. I'll leave it open, whether this applies for the flash point.
"when N-organics burn, all sorts of stuff is formed" – yes, but which compounds are actually formed is of interest.
If pyridine is a major constituent of cigarettes or their smoke, this is clearly relevant to mention it briefly.
(2) Pyridine has a harmonised classification (which involves quite a complex process) saying it fulfills the criteria for Acute Tox. 4 (intake, skin, inhalation). Yes, quite some other chemicals do fulfills these criteria, but way not all.
(5) As above, way not all organics fulfill the criteria for Flam. Liq. 2.
(6) The conclusion of the IARC evaluation most recent version is a must for the article. Please note that some updating would be needed here.
(7) The IARC evaluation linked above states: "Regarding the key characteristics of carcinogens, there is weak evidence that pyridine is genotoxic." Hence, the sentence in the article needs to be amended accordingly (remove neurotoxic and clastogenic effects).
--Leyo 21:40, 6 May 2021 (UTC)
I'm not planning on responding to this on a point-by-point basis but I do share Smokefoot's distaste for this style of safety section, which I tend to think of as an SDS written as prose. The result is too many different pieces of data being presented in no particular order, with the reader being left to decide/guess what the major hazards are. Most of the numbers can be handled by the chembox and the body text should discuss the key points in a narrative manner. --Project Osprey (talk) 22:43, 6 May 2021 (UTC)
A section on hazards is clearly different from a MSDS. Also e.g. HSDB isn't a MSDS. Chemical hazards belong to an article as syntheses, uses etc. do.
To be clear, the Hazards section would merit some improvements, updates and also some removals, but by no way such a clear-cut. --Leyo 23:49, 6 May 2021 (UTC)
I've re-worked the section in my sandbox for your consideration. I'm happy for either of you to make edits there. I hope that better sectioning has made it more coherent. Information relating to animal studies and on its metabolism (which told us what it gets turned into but not what those things might do) has been removed but most of the rest is retained.
Looks good to me. Thank you Project Osprey. --Smokefoot (talk) 12:19, 7 May 2021 (UTC)
I will need to have a closer look, but in general, the structure has improved. May I ask why you removed the metabolism including the diagram? Please note that this part has even remained after Smokefoot's clear-cut. --Leyo 15:05, 7 May 2021 (UTC)
Metabolism of pyridine
I've added the image here for the sakes of discussion (and also so I can reset the indents). The existing paragraph opens with a sentence on whether pyridine is carcinogenic and then discusses its metabolites, but there's no any indication as to how the metabolites might relate to cancer. In fact, there's no discussion on the significance or fate of the metabolites at all. I'm not opposed to having a section on its metabolism, provided it tells us something important or interesting. I lack the skill to write such content and what we had was of poor quality so I just deleted it. --Project Osprey (talk) 16:04, 7 May 2021 (UTC)
Well, I think it is generally of importance what happens to a chemical in the human body after it has been taken up. The metabolites may thus briefly be mentioned. I made a suggested addition, i.e. in a separate section, to your sandbox. --Leyo 22:23, 1 June 2021 (UTC)
That's fair enough. I've pushed the changes across onto the main page. --Project Osprey (talk) 08:40, 2 June 2021 (UTC)

refs

  1. ^ a b Record of Pyridine in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. ^ "Database of the (EPA)". U.S. Environmental Protection Agency.
  3. ^ a b c d Pyridine (PDF). Washington DC: OSHA. 1985. {{cite book}}: |work= ignored (help)
  4. ^ "Pyridine MSDS" (PDF). Alfa Aesar. Retrieved 3 June 2010.
  5. ^ Aylward, G (2008). SI Chemical Data (6th ed.). ISBN 978-0-470-81638-7.
  6. ^ a b c International Agency for Research on Cancer (IARC) (22 August 2000). "Pyridine Summary & Evaluation". IARC Summaries & Evaluations. IPCS INCHEM. Retrieved 17 January 2007.
  7. ^ Shimizu, S.; Watanabe, N.; Kataoka, T.; Shoji, T.; Abe, N.; Morishita, S.; Ichimura, H. "Pyridine and Pyridine Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_399. ISBN 978-3527306732.
  8. ^ Bonnard, N.; Brondeau, M. T.; Miraval, S.; Pillière, F.; Protois, J. C.; Schneider, O. "Pyridine" (PDF). Fiche Toxicologique (in French). INRS.
  9. ^ Junk, G. A.; Ford, C. S. (1980). "A review of organic emissions from selected combustion processes". Chemosphere. 9 (4): 187. Bibcode:1980Chmsp...9..187J. doi:10.1016/0045-6535(80)90079-X.
  10. ^ Hawthorne, Steven B.; Sievers, Robert E. (1984). "Emissions of organic air pollutants from shale oil wastewaters". Environmental Science & Technology. 18 (6): 483–90. Bibcode:1984EnST...18..483H. doi:10.1021/es00124a016. PMID 22247953.
  11. ^ Stuermer, Daniel H.; Ng, Douglas J.; Morris, Clarence J. (1982). "Organic contaminants in groundwater near to underground coal gasification site in northeastern Wyoming". Environmental Science & Technology. 16 (9): 582–7. Bibcode:1982EnST...16..582S. doi:10.1021/es00103a009. PMID 22284199.
  12. ^ National Occupational Exposure Survey 1981–83. Cincinnati, OH: Department of Health and Human Services, Public Health Service, Centers for Disease Control, National Institute for Occuptional Safety and Health.

Chiral Lewis acid

Chiral Lewis acid: according to talk is missing various information. The article has not substantially improved since this issue was raised in November 2013, except for some proofreading. –LaundryPizza03 (dc̄) 01:11, 3 June 2021 (UTC)

List of unsolved problems in chemistry

I encountered this from its expert needed tag, and I believe that its tag is well-justified. Firstly, the list seems to be incomplete (which specifically applies to the expert tag). Secondly, the article cites no compiled lists of unsolved problems in this discipline, failing WP:SYNTH. (I think this topic is notable, however.) Finally, items may be out of date — I removed an item about photochemistry that isn't a problem in the discipline and has been actively researched since the question was posed in 2006. –LaundryPizza03 (dc̄) 03:32, 3 June 2021 (UTC)

Chiral resolution

I have never heard a chemist use the term "chiral resolution". I have resolved enantiomers and heard a lot discussion of the topic, but chiral resolution? It doesnt make sense. Is chiral an adjective to describe a type of resolution. I searched Organic Syntheses, which has about 70 resolutions. In the few articles that I searched, they resolve but they report no chiral resolution. Just sayin'.--Smokefoot (talk) 17:28, 26 March 2021 (UTC)

I agree. I suspect it came about as an article title because Resolution (disambiguation page) has so many entries. The short section at Racemic_mixture#Resolution would suggest we could just call the page Resolution (chemistry) and if others commenting here can't think of a better title, I suggest you do that move. Mike Turnbull (talk) 18:16, 26 March 2021 (UTC)
Google scholar has a lot of articles where "chiral resolution" is part of the title[2]. Christian75 (talk) 20:59, 26 March 2021 (UTC)
Good point. The (anecdotal) fact that no chemist that I know uses the term conflicts with the Google hitlist. --Smokefoot (talk) 23:44, 26 March 2021 (UTC)
I more commonly hear it called "enantiomeric resolution". That seems also a clearer description, since although there are diastereomeric intermediates in some cases, the context is of enantiomers not other chiral aspects. DMacks (talk) 04:34, 27 March 2021 (UTC)
"enantiomeric resolution" returns 7790 results in Google Scholar, v.s. 14500 for "chiral resolution". I'd suggest keeping the title as is and adding the alternative name to the lead; I have already done the latter. –LaundryPizza03 (dc̄) 08:27, 6 June 2021 (UTC)

Monatomic redirect

I have proposed that Monatomic be retargetted from Monatomic gas to Atomicity (chemistry) at Wikipedia:Redirects for discussion/Log/2021 June 11#Monatomic. The discussion would benefit from the input of those who understand the subjected better than me. Thryduulf (talk) 23:15, 11 June 2021 (UTC)

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