Wikipedia talk:WikiProject Chemistry/Archive 52

Molecular graphics
Molecular graphics is a disaster zone. Huge amounts of the content are unreferenced and likely basedon OR, and much of the content seems to be disorganized and repetitive. I have attempted to remove some of the fluff, including textbook-like image labels that included an in-text description of an image that was deleted in 2019. –LaundryPizza03 ( d c̄ ) 07:38, 19 April 2022 (UTC)

What is the deal with User:Prototyperspective?
Seems to be adding content from new issues of Science and similar journals. "Researchers have found ..." "A recent study shows...". Check out recent changes in Monoterpene. The contributions are not awful, but IMHO, misguided in the sense that Wikipedia is a forum for settled knowledge and, ordinarily at least, we dont do news. --Smokefoot (talk) 21:06, 24 April 2022 (UTC)

User script to detect unreliable sources
I have (with the help of others) made a small user script to detect and highlight various links to unreliable sources and predatory journals. Some of you may already be familiar with it, given it is currently the 39th most imported script on Wikipedia. The idea is that it takes something like and turns it into something like
 * John Smith "Article of things" Deprecated.com. Accessed 2020-02-14.
 * John Smith "Article of things" Deprecated.com. Accessed 2020-02-14.

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

The script is mostly based on WP:RSPSOURCES, WP:NPPSG and WP:CITEWATCH and a good dose of common sense. I'm always expanding coverage and tweaking the script's logic, so general feedback and suggestions to expand coverage to other unreliable sources are always welcomed.

Do note that this is not a script to be mindlessly used, and several caveats apply. Details and instructions are available at User:Headbomb/unreliable. Questions, comments and requests can be made at User talk:Headbomb/unreliable.

- &#32; Headbomb {t · c · p · b}

This is a one time notice and can't be unsubscribed from. Delivered by: MediaWiki message delivery (talk) 16:01, 29 April 2022 (UTC)

Redox area merits attention
The following articles touch on big complicated themes: Probably more articles on this theme exist.--Smokefoot (talk) 15:05, 3 May 2022 (UTC)
 * redox (page views: 1,340/day)
 * reducing equivalent comment: it might be merged into reducing agent. (page views: 24/day)
 * electron equivalent comment: see previous entry  (page views: 4/day)
 * reducing agent comment: would be useful to distinguish electron transfer kind of reduction vs hydride reduction and hydrogenation. (page views: 453/day)
 * oxidizer redirects to oxidizing agent. But akin to reducing agent, we might distinguish O-atom transfer from electron transfer.  My guess is that many nontechnical readers are more interested in oxidizers from the safety perspective and not so keen on organic syn.  (page views: 681/day)
 * redox potential (page views: 6/day)
 * hydride seems ok but covers a lot of territory. (page views: 196/day)
 * hydride reducing agents, readers would probably benefit from such an article listing the main borohydrides and various aluminum hydrides. Almost a disambiguation article.  Maybe one exists and I missed it.
 * Organic redox reaction comment: scope is murky (page views 63/day)
 * one-electron reduction was recently merged into redox
 * partial oxidation comment: seems to be mainly oxygenation reactions, stopping short of full combustion. (page views: 23/day)

"Successfully de-orphaned! ..."
User:Herravondure is removing orphan tags on articles with the edit note "Successfully de-orphaned" but no links are being created, so not so successful.--Smokefoot (talk) 14:16, 2 May 2022 (UTC)

What articles are you referring to? I do deorphan articles, and if I did that to one with nothing linking to it that was my bad, but I am not doing this intentionally. Herravondure (talk) 14:28, 2 May 2022 (UTC)
 * Related point: Regardless if they're manually tagged or not, orphan pages are detected and listed by bots, in this project there are [211 pages] at present. --Project Osprey (talk) 14:43, 2 May 2022 (UTC)
 * Do you happen to know how often that page updates? Herravondure (talk) 15:35, 2 May 2022 (UTC)
 * It would appear to auto-update weekly. --Project Osprey (talk) 15:44, 2 May 2022 (UTC)
 * Probably someone with tools should revert most of User:Herravondure's edits.--Smokefoot (talk) 17:01, 2 May 2022 (UTC)
 * I'm not really seeing the problem here. Many of the recent chemistry links seem to be coming from Glossary of chemical formulae. --Project Osprey (talk) 17:52, 2 May 2022 (UTC)
 * Well, many articles are listed as removed from orphanage, but the editor is not adding the links that would de-orphanize. The editor is simply removing tags. Nothing is being done.--Smokefoot (talk) 18:11, 2 May 2022 (UTC)
 * Yeah, but when you de-orphan, you're adding links to that page from other pages. The only edit you make to the de-orphaned page is to remove the tag. That's what I'm seeing, lots of link were made from Glossary of chemical formulae to a load of orphaned articles, which had then been de-tagged. --Project Osprey (talk) 18:31, 2 May 2022 (UTC)
 * Question for Herravondure: what article links back to Fructose-asparagine that was recently detagged? Graeme Bartlett (talk) 04:20, 3 May 2022 (UTC)
 * That's probably the article Smokefoot found. I have been adding chemical orphans that I have failed to deorphan thus far to the Glossary of chemical formula e article. I do them in small bunches, so I must have thought I added that one when I didn't. I have now added it to the glossary. Herravondure (talk) 15:56, 3 May 2022 (UTC)

Creating a template?

 * Useful links:
 * Infobox material usage (33)
 * Infobox material usage (33)

I originally posted this at the Teahouse, but upon advice of the venerable Mr Turnbull I have posted it here too.

Hi, I just noticed whilst browsing through List of named alloys that none of the alloys have infoboxes, and I'm sure it would be a useful idea. I just came here to ask two things, would it be useful (to create an infobox) and should I also make a navbox for alloys? Thanks. My username is actually based off an alloy too! X-750 Rust In Peace... Polaris 22:32, 11 May 2022 (UTC)


 * Hi @X750, I saw your question at the Teahouse. Many alloy articles here and on other language Wikipedias use Infobox material. See 7075 aluminium alloy and Constantan. That infobox isn't able to include the components of the alloy, but that might be a place to start. StarryGrandma (talk) 23:04, 11 May 2022 (UTC)
 * Thanks, . I saw that infobox and I was actually going to use that as my substrate. What do you personally think should be included on the new template? Most of the fields are covered, but things such as composition are probably going to be one of them, similar to the chemical formula present on Infobox drug, but instead of a formula having the % ranges for each element present in said alloy. I was thinking a market names/alternate names section too for alloys such as inconel that have variations, a distinction between different types of alloy (e.g superalloy, nickel-chromium, etc), the UNS number, and that's all I can really think of. Cheers X-750 Rust In Peace... Polaris 23:25, 11 May 2022 (UTC)
 * Actually nine of our articles about specific alloys do have chemboxes, but that is obviously a small minority. But I don't think that box (as it currently exists) is well-tailored to alloys because so much assumes a molecular or ionic substance. We would need a sentinal value for SMILES to avoid a diagnostic for having no SMILES. And we'd need to inhibit mol-wt even though there would be a stoichiometric-composition formula. We have a similar problem for polymers, where mol-wt is either for the repeating unit (that's especially mis-leading for non-alternating co-polymers) or the molecular formula and weight need some typical lengths or "n" coefficients (chembox doesn't have a standard for that). Infobox material looks like a better start, just needs composition and some database tokens (even already our materials should be including that in the infobox, not just in the lede). Drugbox and chembox have equivalent internal handling of molecular formulas. But for material (including alloy) should it should render as a ubl of the components rather than a "molecular formula" type of output? DMacks (talk) 23:33, 11 May 2022 (UTC)
 * Correct, we would have something pretty much akin to a parameter such as composition, and then a ubl, as that's the easiest way I believe we can implement them. I haven't examined polymers so much, and I did not intend to use molecular formulas, weights, SMILES or anything of the sorts, just something akin to what's present at Infobox drug. For the database tokens, which is the UNS number, is there another internal system within Wikipedia that can categorise these things? I'm not too well-versed in the technical things (I do have experience with modules at Wiktionary if that's helpful at all), so I'd like some pointers as to what I should go about doing there. X-750 Rust In Peace... Polaris 23:45, 11 May 2022 (UTC)
 * Check out my hacking on ferrotungsten. Only reader-visible bug is that it should display a label of "Chemical composition" instead of "Chemical formula". It would be easy to implement a switch field that controls that output and also inhibits things that don't apply. Careful talking about drugbox, it includes essentially everything chembox does, and more. DMacks (talk) 23:51, 11 May 2022 (UTC)
 * Interesting, but I don't have the expertise nor the motivation to implement such a switch, perhaps once I publish the template you could do a bit of fiddling in the sandbox of the respective template? As for drugbox, I just personally have more experience with it, as I've used it often to write articles about, well, drugs & antibiotics.X-750 Rust In Peace... Polaris 23:58, 11 May 2022 (UTC)
 * Allow me to join in. I've worked on developing and  templates, but I am no chemist.
 * Having read this, I suggest to expand Infobox material with a extra section (subheader) "Alloy", to appear in top ;-). It can contain alloy-specifics, such as composition. If I understand correctly, some parameters (properties) from eg Chembox could be added (please start hinting). As said, for the chemical details (parameter subtleties) I'll have to be educated. -DePiep (talk) 02:20, 12 May 2022 (UTC)
 * Started sandboxing Infobox material (/testcases). I saw  ferrotungsten. I think a dedicated parameter(s) for alloys is preferable. Do you think we should pursue alloys-in-? Or IB materials? -DePiep (talk) 04:43, 12 May 2022 (UTC)
 * Oh dear I should've read this sooner, check out User:X750/Infobox alloy for what I have so far.
 * If you have the time, a double-pronged approach can be done (i.e. you do you, me do me), and we can decide via consensus/vote of some sort which one we can roll with. Cheers X-750 Rust In Peace... Polaris 04:52, 12 May 2022 (UTC)
 * Things happen. Preferably I don't work parallell=double. Apart from parameters you added to the IB-material (which?), what is the alloy feature you aimed at? (IMO, a dedicated section, in top, could handle the alloy specs nicely). -DePiep (talk) 04:58, 12 May 2022 (UTC)
 * I am still working on it! I'll ping you when I think it's almost ready for publishing. Understood point on working in parallel. X-750 Rust In Peace... Polaris 05:00, 12 May 2022 (UTC)
 * Hey, I've drafted up a testcase at User:X750/Infobox alloy/testcases, see what you think. I was also wondering, is there something we can change in the documentation so that units are automatically added? Although that would pose problems if people have a specific unit and need to convert them... can we put the convert template in there somehow too? Thanks X-750 Rust In Peace... Polaris 01:27, 13 May 2022 (UTC)
 * OK, good to see. Question on content: what does the chem formula mean, for alloys? AFAIK, an alloy is not a compound, but more like a mixture. Does the formula need a clarification then?
 * About the presentation: I still think the alloy properties should be grouped under one subheader. For me, a layman reader, it makes things much more clear right away (for example, that UNS and SAE are alloy codes). The existing parameter type can stay (and get label "Material type"). Be as specific as possible, especially if its free!
 * Also, I think it can easily be an extension of current (as I did in the sandbox). Makes maintenance of those parameters easier, and no conflicts foreseen. I'll add the parameters you added to that sandbox. See /testcases. -DePiep (talk) 06:37, 14 May 2022 (UTC)
 * Yes, I'm leaning more and more towards simply expanding Infobox material. Also, as to your question as to chem formula, it's description in the doc simply says Chemical formula of the alloy (if listed), please hard-code with subscripts. Which means if the formula is listed, it can be added as it's a suggested parameter. And yes, I shall amend that label you have mentioned. I just have a singular question, at the Infobox material/testcases, you have put "T2 tool steel" under type, I presume that is a filler as is SAE999. I think we should also rename the subheader to "Alloy properties". Looks like it's coming together. I'll sort the navbox out, I've got experience with music group navboxes, and I'll simply follow the layout of something like Hydrides by group, with the groups probably shaping to be "non-ferrous", "ferrous", and under non-ferrous, probably division into nickel-based, aluminium-based, etc, and others. I'll be using for the navbox too, so if you know any pages that might be missing just mosey on over & add it to the page. Sound good? X-750 Rust In Peace... Polaris 10:01, 14 May 2022 (UTC)
 * Afterthought: We have footnotes for a reason, we could simply explain it in the footnotes, or add something like chemical_formula_note. Quite obvious innit? X-750 Rust In Peace... Polaris 10:03, 14 May 2022 (UTC)
 * If you think the chem formula is a correct presentation, it's fine with me. (but, if it is a ratio like the percentages &mdash; not a compound, it is wrong). Anyway, we can proceed and improve later.
 * Yes I took some random data, eg 'T2 tool steel'. Just testing the parameters.
 * I've adjusted the /sandbox, see testcases.
 * The navbox is a different topic. I ignore that one for now here.
 * I strongly propose to make Infobox material/sandbox the proposed version, not your subpage (I've made some other needed changes in there already). I understand current version reflects all your proposals. So, publish? -DePiep (talk) 09:23, 15 May 2022 (UTC)
 * Ah that chemical formula thing, it's optional, we'll let the other editors include if they want to. I'll leave it blank when editing articles for the sake of not confusing readers. Yes, I will handle the navbox. You can brush that away.
 * Yes, to your proposal too, very pleased with how the testcases has turned out. Full steam ahead. X-750 Rust In Peace... Polaris 10:41, 15 May 2022 (UTC)
 * ✅. -DePiep (talk) 11:06, 15 May 2022 (UTC)

Infobox material: changes



 * Boldly added {{para|synonym, synonyms]]; changed label for {{para|type}} (live now)
 * Alloy (in sandbox):
 * {{para|alloy type}}
 * {{para|alloy composition}}
 * See testcases. -DePiep (talk) 04:39, 12 May 2022 (UTC)


 * To consider:
 * {{para|UNS_identifier}} for Unified numbering system
 * {{para|SAE identifier}} for SAE steel grades
 * from OP. -DePiep (talk) 08:00, 12 May 2022 (UTC)
 * also applying comments by X750, above. -DePiep (talk) 09:23, 15 May 2022 (UTC)

{{done}} Updated {{tl|Infobox material}} as discussed. Created {{tl|Infobox alloy}} synonym. -DePiep (talk) 11:06, 15 May 2022 (UTC)

Merger discussion for Chemical oceanography
An article that you have been involved in editing&mdash;Chemical oceanography&mdash;has been proposed for merging with another article. If you are interested, please participate in the merger discussion. Thank you. Chidgk1 (talk) 06:52, 18 May 2022 (UTC)

ECHA InfoCard
This isn't my area but I thought this might be something worth flagging. ECHA InfoCard used to be a redirect to a section of European Chemicals Agency but that section no longer exists. However that redirect has incoming links from >10k articles - I assume it's in a template somewhere. I'd suggest this needs a bit of attention - either the template needs tweaking or some information needs to be added about the InfoCard. Le Deluge (talk) 14:55, 8 May 2022 (UTC)
 * The link is made in Chembox and Infobox drug. Heavily tied to wikidata and its ID property. If the European Chemicals Agency article does not contain a good target, nor any other article, one wonders whether it is important. -DePiep (talk) 16:17, 8 May 2022 (UTC)
 * The ECHA article is not very good (e.g. it has external links in the body of the text and few/no secondary sources). I'm happy to add it to my "to-do" list and at the same time create a subsection on the Infocard, which is a fairly useful part of the European regulatory system and gives Wikipedia a less US-centric view. Thanks, for highlighting this. Mike Turnbull (talk) 16:52, 8 May 2022 (UTC)
 * ✅ The redirect now goes to a newly-created section of the article, which I'm continuing to improve. Mike Turnbull (talk) 09:22, 10 May 2022 (UTC)


 * By Wikidata: the ECHA Infocard has no lang-wiki articles anywhere. The good news is: both chem templates here pull the ECHA ID from Wikidata, and so some 10k articles have this external Infocard ID+link. Data is well (mass-)maintained at WD, IIRC. -DePiep (talk) 19:43, 8 May 2022 (UTC)


 * See ECHA InfoCard. Good work. -DePiep (talk) 11:39, 10 May 2022 (UTC)

Wikidata datamodel

 * For an update proposal, see WD:WP Chemistry # ECHA_Substance_Infocard: datamodel_check. -DePiep (talk) 05:50, 21 May 2022 (UTC)

JSmol model for zwitterionic lysine is wrong
A comment on Talk:Lysine just noted that he JSmol model for zwitterionic lysine is wrong! The molecule should be protonated on the epsilon amino group!. Could I get this double-checked by a chemist? T.Shafee(Evo &#38; Evo)talk 00:24, 18 May 2022 (UTC)
 * I think this is debatable and I'm not sure how the issue should be resolved. The change needed to show the epsilon-protonated version instead of the alpha-protonated version is to alter the relevant Smiles to [NH3+]CCCCC(N)C(=O)[O-] instead of its current NCCCCC([NH3+])C(=O)[O-] in the Chembox. However, in most other amino acids the relevant Zwitterion is the alpha one (i.e. they don't have a second protonatable centre) and even in lysine the balance of protonation between the alpha and epsilon nitrogens will depend on factors such as their respective pKa, the solvent and the temperature. On balance, I think my preference would be to remove the Zwitterion and the protonated Zwitterion from the Chembox altogether and add some comment about pKa etc. (with reliable sources) to the body of the article or on Lysine (data page), if it is important to readers that this be discussed. Mike Turnbull (talk) 11:20, 18 May 2022 (UTC)
 * Hi. If we consider Lys only as a molecule isolated from biological systems (as the model does), then we can fairly reliably assume which amino group will be protonaned most of the time. The main factor that will change pKas under this condition is the proximity of -COO- group on the alpha carbon atom. This group has a -M effect. This means that electron density of alpha -NH2 group will be slightly pulled towards it compared to epsilon -NH2 group. As such, the lone pair on the epsilon -NH2 group will be more able to bind to a proton. Epsilon group pKa will be considerably higher than alpha group pKa. And naturally, empiric evidence supports this claim -- please see a table of amino acid pKa values, such as this. 37.221.242.34 (talk) 12:10, 18 May 2022 (UTC)
 * OK, that's a convincing argument even though the precise values in the linked URL don't quite match what our data page says. More significantly, all the interactive images in the article gave the wrong absolute stereochemistry for (S)-lysine, so I've changed them all. Please check and make sure everyone can be happy with the outcome. Mike Turnbull (talk) 15:15, 18 May 2022 (UTC)
 * Good catch about the stereochemistry! It would be great if we could somehow document when SMILES is omitting that info (or better, as you did, actually include it). But your two "zwitterionic" forms have the carboxyl still protonoated. DMacks (talk) 15:27, 18 May 2022 (UTC)
 * Oops! Now corrected. That's why we need the wisdom of crowds. Thanks . Mike Turnbull (talk) 15:57, 18 May 2022 (UTC)
 * I wonder what the shortest wikilink-following path is between swiss cheese model and mean free path :) DMacks (talk) 16:15, 18 May 2022 (UTC)


 * Worth noting that in the crystal structure of pure lysine, it's primarily the alpha amino group that's protonated, although there is a bit of H-atom disorder near one of the two epsilon amino groups: Angew. Chem. Int. Ed. (2015), 54, 3973-3977, CSD entry CUFFUG. The Chembox PNG images (File:Lysine-from-xtal-3D-bs-17.png and File:Lysine-from-xtal-3D-sf.png) reflect this. --Ben (talk) 19:05, 18 May 2022 (UTC)

Thanks,, I'll let you fight this out with the IP editor. This is well beyond my pay grade. At least you both now know how to alter the SMILES in the article to reflect whatever you decide is "the truth" (or "the most useful")! Mike Turnbull (talk) 19:16, 18 May 2022 (UTC)


 * So glad that I referred this over to this group. Very interesting discussion! T.Shafee(Evo &#38; Evo)talk 22:52, 18 May 2022 (UTC)
 * I've also updated the zwitterionic model for Arg, even though it took me three tries now it should be (more) correct. The main driving force here is of course the delocalization of the positive charge (even shown in a picture in the article); the discussed pKa difference is even greater. Hopefuly I didn't mess it up instead. 37.221.242.34 (talk) 05:51, 19 May 2022 (UTC)
 * The catch with many articles on amino acids is that the free amino acids are rare (I think, I have been looking for a source of occurrence of free amino acids). Some Wiki articles on amino acids actually discuss amino acid residues, but dont make that distinction clear.  --Smokefoot (talk) 13:42, 22 May 2022 (UTC)
 * Agreed that samples of the free amino acids may be rare but here we are discussing the substances/IDs and representations in the Chemboxes. I've now checked these for all proteinogenic amino acids to ensure, inter alia, that the Jmol depictions are accurate/useful and that we have more comprehensive IDs: L, D/L and D (in that order) in many cases. Arginine and aspartic acid) needed overhaul and careful updating — which I now believe to be correct. Mike Turnbull (talk) 15:39, 22 May 2022 (UTC)

JSmol in infobox Chembox
Here the template background for Chembox having Jmol (or JSmol). In short: Jmol uses SMILES, but can be overwritten.


 * FYI: This is what can do with SMILES and Jmol. (The demo uses indexes 1-4, see code).
 * A Regular, default: Jmol reads SMILES and creates the interactive image at the external link ✅
 * F Ferrocene: its SMILES is incorrect for 3D, (another SMILES) is fed an adjusted SMILES string &rarr; shows OK in 3D ✅
 * L Lysine (Zwitterion): SMILES read by Jmol (default route), 3D image under discussion
 * L(none) Lysine Zwitterion: same SMILES but none &rarr; Jmol does not show for this one (no error)

Not done: possibly an adjusted SMILES string would show 3D correct in Jmol.

-DePiep (talk) 13:06, 18 May 2022 (UTC)

Tammann and Hüttig Temperature
Hi. I've created a Tammann and Hüttig Temperature article recently. Would love to see some feedback on it. It's pretty short and mostly serves purpose of a data page. Please checkout. Thanks. -- AXO NOV  (talk) ⚑ 23:46, 28 May 2022 (UTC)
 * I have renamed it (and reviewed for copyright infringement). Graeme Bartlett (talk) 12:04, 30 May 2022 (UTC)
 * It's very specialised stuff. It presumable needs links to and from premelting? Who was Hüttig? --Project Osprey (talk) 12:14, 30 May 2022 (UTC)

Borax as a mineral species
Discussion at Talk:Borax --Kent G. Budge (talk) 16:05, 3 June 2022 (UTC)

Graphite as a mineral species
I will set up a discussion akin the borax one above at Talk:Graphite. Quick reading of Greenwood and Earnshaw indicates that both mineral and synthetic graphite are widely used commercially. --Smokefoot (talk) 02:02, 10 June 2022 (UTC)

Updating naming conventions for groups
I think it's due time to take a look at the content at Naming_conventions_(chemistry) to see if the wording and examples need updating, and then work on bringing article titles in line with the conventions we've confirmed. Looking specifically at the first subsection: As for the second subsection: Please share comments and I will draft a proposed revision for us to consider and will link below. Mdewman6 (talk) 01:38, 12 April 2022 (UTC)
 * Compound class and functional group are not clearly differentiated, using alkane as an example of a functional group, when in fact alkyl is the associated functional group that has a separate article. Also, an internal link to functional group would certainly be helpful to readers.
 * The first subsection goes on to confusingly state where the group is not considered to be functional, e.g. phenyl, trimethylsilyl, or is important for some other reason, e.g. trifluoromethylsulfonyl. The examples given are typically referred to as functional groups and can be the "functional" part of a molecule in chemical reactions, so this differentiation is at best confusing, if not completely unwarranted and incorrect.
 * It states that the normal IUPAC name (under general nomenclature) for the group is used. This likely runs into WP:COMMONNAME problems. I argue the article on one of the examples given, trifluoromethylsulfonyl, should be at its common name, triflyl, as the lede suggests as well. We should consider revising the guidance here to call for the use of names most commonly used in reliable sources, akin to the guidance for naming organic compounds.
 * Finally, it states...without adding the word "group". This is apparently an effort to conform to WP:CONCISE, but one of the most prominent examples, Phenyl, currently has its article at Phenyl group contrary to the current convention. The current format for article titles of functional groups vary even further, e.g. Tolyl groups. Personally, I do favor adding "group" to the titles of such articles, but recognize there are arguments both ways. Colloquially, chemists will refer to functional groups as nouns (e.g. "that compound has three phenyls" or something) but they are really adjectives that should modify a noun ("group") when used as an article title.
 * I generally agree with the guidance here, except that the article titles for these articles are presently all over the place, as can be seen by following links from Template:ChemicalBondsToCarbon. Many have the format "Organo[element] compound" but are confused by WP:PLURAL as to whether or not the plural is warranted because the article is about a class, thus some are "Organo[element] compound" and some are at "Organo[element] compounds". Using the "chemistry" form of the name avoids this issue. Other articles are at related titles if the article for the related topic has been sufficiently developed, e.g. Organolithium reagent, with the other versions as redirects, which I think is okay. So, here I think we can just emphasize the current guidance and then bring all the affected articles into compliance and be consistent.

I have a rough draft of a proposed revision at User:Mdewman6/Chemical groups naming convention. The only major change is to specify that articles on functional groups include "group" in the title, e.g. phenyl group, not just phenyl. It also makes clear to defer to WP:COMMONNAME rather than going with whatever IUPAC may say. Please comment; if there are no objections I would like to institute these revisions in the near future and bring consistency to the titles of the affected articles. Mdewman6 (talk) 02:05, 19 April 2022 (UTC)

Any comments? I don't think we need an RfC for this, but I'd prefer not to go with WP:SILENCE for implementing a naming convention change either. But, given the page views the proposed version has received, I will take silence as consensus if there is no further discussion. Mdewman6 (talk) 02:58, 20 May 2022 (UTC)
 * Support. I think this proposal improves Wiki, because it standardises naming (-patterns) without enforcing nonintuitive routes. Maybe strengthen support by notifying/proposing at WT:MOS/Chemistry? After all, it is a MOS change. (I am not specialist in this chemistry; I do work with and  here). -DePiep (talk) 07:19, 20 May 2022 (UTC)
 * I will add a notification of this discussion at the MOS page. Mdewman6 (talk) 21:14, 20 May 2022 (UTC)
 * Support, but it has a major gap. What kind of disambiguation should be used for these articles, particularly for compound classes and functional groups that are named after their parent compound? Should we use plurals like Hydrazines or parentheticals like Diphosphene (functional group)? –LaundryPizza03 ( d c̄ ) 09:18, 20 May 2022 (UTC)
 * Excellent point. I was mostly trying to make sense of the naming convention as it stood, but we should definitely say something about these cases. I just noticed Wikipedia_talk:Manual_of_Style/Chemistry, where an example of yet another disambiguation strategy is given, Fulvalene (compound class). For groups based on inorganic parent compounds, another method is to add an organo- prefix, like Organophosphine vs. Phosphine, but I'm not sure I like this (certainly a good redirect at least). I lead toward thinking we should favor using plurals for this, which would fully comply with WP:PLURAL and WP:DIFFCAPS and also favor natural disambiguation over parenthetical disambiguation. I feel like a majority of such articles use the plural at present, like Silanes, Boranes, etc. but I'm not certain. Of course, if the article is setup to be more about the functional group than the class of compounds, then [singular] group could be considered per the above on a case by case basis. Hatnotes between the parent compound article and the compound class articles should also be standard. Anyway, I'll amend the draft soon to reflect this and we can see if like it or not. Mdewman6 (talk) 21:14, 20 May 2022 (UTC)
 * I support a change to the naming convention, in particular for adding "group" to the articles mainly about the functional group. For compound classes, I was raising this issue back in 2020. I like the idea of adding the "s". Yet another convention is shown in Alcohol (chemistry) (which has redirect alcohols) and Salt (chemistry) (with redirect Salts). Even though Fulvalene (compound class) is a current example in our convention, it is the only article using it. Also would anyone like to write the article on Compound class? We already do have "Functional group". Graeme Bartlett (talk) 22:28, 20 May 2022 (UTC)
 * Well, Alcohol (chemistry) is analogous to Alkane and other traditional compound classes and should be singular under the current and proposed naming convention, it's just that alcohol has parenthetical disambiguation because of all the other uses of alcohol, and a recent RM decided there was no primary topic. But I think we can keep those singular while using the plural for compound classes named after parent compounds; I don't think we want Alkanes, Ketones, Carboxylic acids, Esters, etc. as titles instead of the singular, which would be a widespread change from the status quo. Mdewman6 (talk) 00:06, 21 May 2022 (UTC)
 * Also, I think we can use the plural for salts/esters of acids, which you also mentioned in your last discussion. So Phthalate should be at Phthalates, then there is Benzoates, etc. In many cases, these will be redirects to the parent carboxylic acid, or in rarer cases the parent carboxylate, but notable cases will have their own articles, which should be at the plural to analogously differentiate them from the carboxylate.

I added a paragraph to the draft section (User:Mdewman6/Chemical groups naming convention) that is an attempt to capture the situations discussed above. If implemented, we'll need to revise Manual_of_Style/Chemistry which suggests parenthetical disambiguation. Mdewman6 (talk) 22:06, 21 May 2022 (UTC)
 * (late to the party) I support these functional-group, class, parent-vs-derivative and associated singular/plural approaches. Has Wikipedia talk:Article titles or similar sitewide been pinged about this discussion? DMacks (talk) 22:48, 21 May 2022 (UTC)
 * No, I didn't cast the net that widely, but certainly can and will leave a link there. Mdewman6 (talk) 23:48, 21 May 2022 (UTC)

If there is no further discussion in next 7 days or so, I will plan on implementing the proposal to replace the current section of the naming conventions with the proposed text. I'm sure it could be further refined and tweaked, which can certainly happen going forward, but there seems to be consensus this is at least an improvement over the status quo. Cheers, Mdewman6 (talk) 22:39, 3 June 2022 (UTC)

Discussion at WP:Fringe over some COI edits.
Editors with good working chemistry knowledge might be useful in this discussion at WP:Fringe. It's a question of surprising chemistry claims being sourced to the editor's own papers.

https://en.wikipedia.org/wiki/Wikipedia:Fringe_theories/Noticeboard#Chemical_energy_and_related_articles

ApLundell (talk) 04:40, 10 June 2022 (UTC)


 * Thank you for posting that here. I am the editor who started that discussion, and I don't know how to proceed at this point.


 * About 80 science/chemistry articles on Wikipedia currently include claims about the chemistry of oxygen that are nonsensical in the standard framework of chemistry, confusing, and potentially harmful.


 * These have been added by a single editor, backed up with references to a few papers by that same editor.


 * I've made a list of the problematic articles and edited a few; the editor who added the claims restored them.


 * The statements in question are, frankly, embarrassing to have on Wikipedia. I'd appreciate any advice on how we can go about removing them. (If you think I'm the one who has a problem with perfectly good science here, I'd also appreciate a short note telling me that!)


 * IpseCustos (talk) 14:58, 11 June 2022 (UTC)

Feedback on Draft:Energy-rich species: keep or delete?
In relation to the ongoing discussion about whether oxygen is a "high-energy molecule", I've started drafting an article on "energy-rich species" or "high-energy species". The term appears to be in fairly wide use in introductory material, but I haven't been able to find a decent well-sourced definition of it. It's not quite a dicdef as usage varies and there are several similar terms; it's not quite equivalent to "unstable"; it doesn't really fit into "chemical energy".

I'm honestly undecided whether this article is a good idea. I thought the definition so obvious that spelling it out would be dictionary work, but of course the whole "high-energy oxygen" idea kind of demonstrates that it isn't.

Anyway, in order of preference, I'm asking for offers to take over the draft (yeah, right); opinions that the draft should be deleted (with or without reasons); or opinions that it should be kept and how to improve it. In particular, if anyone can remember a textbook or article that defines the term rigorously, I'd know where to continue looking.

IpseCustos (talk) 18:09, 12 June 2022 (UTC)


 * Feels like WP:NOR. Terms like 'high energy' or 'energy rich' are often used to describe materials, but there is no formal definition, which makes trying to write an encyclopaedia article on those terms fairly pointless. --Project Osprey (talk) 14:41, 16 June 2022 (UTC)
 * Agree with Project Osprey. On the other hand, we (Wiki-chem project) aim to have articles or redirects on commonly used terms.  One possibility is to redirect "Energy-rich species" to Energetic materials, things like ammonium nitrate that blow up spontaneously.  We could expand the article to include exergonic hydrolysis reactions.  One problem with many energy-rich species is that their tendency to release energy depends on another reactant.  Folks call ATP energy-rich, but only if it is contacted with water (or O2 and a spark).
 * BTW, an even more common chem-slang is electron-rich, which redirects to polar effect, I have no idea what polar effect means, so I am considering redirecting to redox potential.--Smokefoot (talk) 15:29, 16 June 2022 (UTC)
 * I think that although there is no formal IUPAC definition for any of these terms, they are sufficiently often used that they form part of the jargon of (bio)chemistry. Thus Wikipedia would be improved by having an article along the lines that proposes and the current draft should be moved into Mainspace. I would be happy to add to it. It needs to have an explanation along the lines of the lead at thermodynamic free energy that in practice only changes in free energy are physically meaningful, so all reactants and products are relevant, with no single one really being the "energy rich" species. Those of us who have made nitrogen triiodide would nevertheless happily call it that! Mike Turnbull (talk) 14:18, 21 June 2022 (UTC)
 * By all means, feel free to edit mercilessly. I disagree that all reactants are relevant, but in the case of nitrogen triiodide it makes no difference as there is only one of them. IpseCustos (talk) 19:53, 22 June 2022 (UTC)

Request for advice from new page patroller
The new article Xerosydryle has a sundry of scientific material in it but from what I see only one source even mentions the term and a quick google search came up with nothing on the term. Am I right in deducing that the article represents trying to establish a new term? If so, Wikipedia would not be the place for such an effort. So if an article by that name were not to survive, is there a recognized topic for the material in the article? Thanks. North8000 (talk) 20:17, 10 June 2022 (UTC)
 * I labelled this as a hoax earlier, but that was contested by . I think Wikipedia would be better off without this page. The topic is an invention by one person. Perhaps AFD is the way to go as there s some controversy. Graeme Bartlett (talk) 02:25, 11 June 2022 (UTC)
 * It is a hoax, as the lead text accumulated clumps of xerosydryle appear as a white-ish fluffy, dry substance, alone makes clear. Water is probably the most studied substance of all and "dry" water is a contradiction in terms. Let's not waste time on WP:AFD. Mike Turnbull (talk) 11:30, 11 June 2022 (UTC)
 * On reflection, I think it is a bit unfair to call the Wikipedia article a hoax. actually did a pretty good job of summarising a load of WP:FRINGE publications, of which 10.14294/WATER.2021.2 is the latest and most egregious (and introduces the neologism xerosydryle). That journal article is so way-out that it actually makes an interesting read as an object-lesson in bad chemistry! PROD is still the way to go for the moment, I think. Mike Turnbull (talk) 12:55, 12 June 2022 (UTC)
 * Then should I use PROD or db-hoax? –Laundry<b style="color:#fb0">Pizza</b><b style="color:#b00">03</b> ( d c̄ ) 13:48, 11 June 2022 (UTC)
 * I'll leave my "in progress" tag just to make sure that somebody doesn't accidentally pass it if the prod disappears. <b style="color: #0000cc;">North8000</b> (talk) 14:22, 11 June 2022 (UTC)
 * I don't know about Xerosydryle but I'm pretty sure that 'dry water' is a real thing. It's essentially large vesicles of water wrapped in a shell of hydrophobic fumed silica. The end result is a fine powder, dry to the naked eye but which is >95% water. Cohesion between the silica particles is strong enough to avoid coalescence of the water. It gets fancy names, as you would expect: liquid marbles, dry water etc. --Project Osprey (talk) 20:41, 12 June 2022 (UTC)
 * If it is a WP:HOAX we don't want to PROD it because we don't want there to be a WP:REFUND option for the perpetrator. WP:PROD is for uncontroversial deletions. Based on the discussion I see here, it does not appear there is consensus on why this should be deleted. It is not clear is onboard with deletion. The right thing to do I think would have been to send this immediately to WP:AFD and have this discussion there. That didn't happen and I'm reluctant to WP:DEPROD because WP:POINTY. ~Kvng (talk) 14:09, 16 June 2022 (UTC)
 * I would support deletion, the article is little more than technobabble.--Project Osprey (talk) 14:19, 16 June 2022 (UTC)

The creator posted the following at the talk page, but did not remove the PROD tag:

–<b style="color:#77b">Laundry</b><b style="color:#fb0">Pizza</b><b style="color:#b00">03</b> ( d c̄ ) 19:17, 16 June 2022 (UTC)

The research by Germano and colleagues is in continuity with the research by Pollak, which has been published on a Q1 journal. The statement that the material in the article (e.g. the Exclusion Zone reported by Pollak) is an hoax, is in disagreements with the reviewers and the editors of several prestigious journals. I have removed the PROD tag, based on the arguments written here and in the Talk page of the article, and on the extra references added. Oakwood (talk) 19:42, 16 June 2022 (UTC)

Regardless, I think that right here is the best place to pick a general direction on this. Flow wise, here are possibilities: Sincerely,<b style="color: #0000cc;">North8000</b> (talk) 19:48, 16 June 2022 (UTC)
 * 1) Send to AFD.  Some of you experts would need to weigh in there.
 * 2) Me mark it as reviewed.
 * I have nominated the page for deletion: Articles for deletion/Xerosydryle. We should be able to get a definitive outcome from that. Graeme Bartlett (talk) 00:17, 17 June 2022 (UTC)

I am a bit confused about the right place where to discuss the deletion: here? in the page 'talk' section? in the deletion talk page? could you please clarify? thanks! Oakwood (talk) 05:52, 18 June 2022 (UTC)
 * Graeme has made the deletion discussion a formal process per WP:AFD. The correct place for further discussion is now at the link in his latest message above (also notified on your Talk Page). As part of any comment you add, it would be interesting to say how you know articles are in the review process, and should be published in the near future from your earlier comment. Mike Turnbull (talk) 10:05, 18 June 2022 (UTC)
 * This is probably not so much a hoax in the sense of a deliberate fraud by the investigator, but anomalous science in which the investigator has deluded or deceived himself. This is claimed to be water behaving in a very non-standard way under ordinary conditions due to supposed unusual supramolecular structure, that is, hydrogen bonding behaving in an unknown fashion.  This seems to be just a different form of polywater.  Robert McClenon (talk) 23:38, 22 June 2022 (UTC)
 * You mean pathological science? –<b style="color:#77b">Laundry</b><b style="color:#fb0">Pizza</b><b style="color:#b00">03</b> ( d c̄ ) 00:54, 23 June 2022 (UTC)
 * User:LaundryPizza03 - Yes. My error.  This is pathological science rather than a hoax.  Although the reported physical properties are different than those reported for polywater, it is still polywater.  The differences in reported properties don't matter, because it isn't a real material and so doesn't have physical properties.  It is polywater and so is pathological science, again.  Robert McClenon (talk) 14:55, 23 June 2022 (UTC)

Good Article assessment: Bisphenol A
Bisphenol A is currently being assessed for Good Article status. I'm aware that we don't usually go in for such baubles, but it seemed a fairly rare example of a non-drug small-molecule which is of public interest. I would welcome input at Talk:Bisphenol A/GA1. --Project Osprey (talk) 12:04, 28 June 2022 (UTC)
 * Well there's baubles, and there is service to society, and this article falls into the latter category. For baubles, you might consider shifting your editing toward Elvis or such.  More seriously, BPA is highly topical for many reasons and I worry that some views on the topic are uninformed, so its important that the world see a balanced technical summary.  --Smokefoot (talk) 13:23, 28 June 2022 (UTC)

User:Ll0103, ref spammer, admin help needed
User:Ll0103 has made several edits over the recent past, always and only citing his primary journal articles. I tried to revert these things, but it would be helpful if some administrator would intercede. I am sure that this person is convinced of the brilliance and notability of their publications, but he's abusing our system. --Smokefoot (talk) 13:08, 21 June 2022 (UTC)
 * They've been at it since 2014, and also using IPs such as User:129.105.149.245. DMacks (talk) 14:25, 30 June 2022 (UTC)
 * They've been at it since 2014, and also using IPs such as User:129.105.149.245. DMacks (talk) 14:25, 30 June 2022 (UTC)

Improved periodic table
Today's XKCD. DMacks (talk) 14:48, 30 June 2022 (UTC)


 * Definitely helps me improving the articles, makes editing so much nicer. I'd contest some carbons though. -DePiep (talk) 14:57, 30 June 2022 (UTC)
 * I preferred yesterday's. --Project Osprey (talk) 15:02, 30 June 2022 (UTC)
 * I keep thinking that its good that the Welsh didnt discover any elements, e.g., Llanfairpwllgwyngyllium.--Smokefoot (talk) 17:03, 30 June 2022 (UTC)
 * Indeed...Of course, if you want something a bit more intellectual, there's always this sonnet... --Project Osprey (talk) 17:07, 30 June 2022 (UTC)
 * Would require three-letter symbol indeed. Still,  all. -DePiep (talk) 18:33, 30 June 2022 (UTC)
 * Thanks for the much needed update. Why not take this opportunity give the long-neglected element zero a place in the table. Its only stable isotope (nothing) is the most noble of all the noble gases. Well-known isotopes include the neutron. Heavier isotopes (such as neutron stars) have not yet been isolated in the lab and perhaps shouldn't be (safety first!). –MadeOfAtoms (talk) 21:22, 30 June 2022 (UTC)
 * zero is such a ... bronze-age concept. Sure it build pyramids and cities and civilisations and clay-based spreadsheets, but what else?
 * No, I think the Periodic Table needs the Imaginary element. Atomic number $i$. Likely diatomic in appearance. Simplifies quantum theory, if not: explains it all. $i$ there's no heaven. At last, even Scerry will admit it's not chemics, nor physics: elements are just math. -DePiep (talk) 22:41, 30 June 2022 (UTC)
 * Somewhere between $1 0$n and $huuuuuge 0$n we find that dineutron has been observed, but it's not a true bound state and tetraneutron might exist. DMacks (talk) 23:51, 30 June 2022 (UTC)
 * Where do we fit Ps positronium? It does have known chemistry: positronium hydride .... Graeme Bartlett (talk) 02:17, 1 July 2022 (UTC)
 * If dineutrons had a say in the periodic table then I'm all for them. And positronium chemistry is a severely cool so it definitely needs its onium atomic number. That's where complex Z should come to the rescue, somehow. (The complex analysis folks must have known this when they called it z). Positronium can be seen as $0 0$n−1$0 0$n+1, the disproportionation of neutral nothing ($0 0$n) (or should it be dinothing?) into a bound state of the nothing anion (Welsh "yn syml electron chi hen ffwl gwirion") and the nothing cation. But I digress. The important thing is safety first: do not look directly at your positronium sample. –MadeOfAtoms (talk) 09:08, 1 July 2022 (UTC)
 * I suppose Positronium could be an isotope of hydrogen with −1 neutrons, even if it's not MadeOfAtoms. Graeme Bartlett (talk) 09:20, 1 July 2022 (UTC)
 * Support "dinothing". -DePiep (talk) 09:32, 1 July 2022 (UTC)

"Sand battery" listed at Redirects for discussion
An editor has identified a potential problem with the redirect Sand battery and has thus listed it for discussion. This discussion will occur at Redirects for discussion/Log/2022 July 5 until a consensus is reached, and readers of this page are welcome to contribute to the discussion. 64.229.88.43 (talk) 22:11, 5 July 2022 (UTC)

""
currently redirects to List of gemstones by species. I find this situation odd, since there are many crystals that are not gems and several gems that are not crystalline. -- 64.229.88.43 (talk) 23:15, 24 July 2022 (UTC)
 * Listed at Redirects for discussion/Log/2022 July 25
 * Deleted via G7 -- 64.229.88.43 (talk) 11:26, 25 July 2022 (UTC)

RfC: PFAS or PFASs?
See -DePiep (talk) 20:49, 7 July 2022 (UTC)
 * I went to this RfC and my impression is that the issue is not specific to PFAS or at the least it's not clear why it should be specific to PFAS and a uniform approach across WP could make sense. Dominic Mayers (talk) 01:43, 25 July 2022 (UTC)
 * All comments, including meta-ones, better be over there. This one is not seen usually, and certainly should not be discussed here. -DePiep (talk) 03:54, 25 July 2022 (UTC)
 * The comment was pointing out that the RfC goes beyond what's going on over there, which is relevant here, but, yes, this point being validly made here, the discussion should continue over there or be moved here, but it should occur at one place. Dominic Mayers (talk) 14:53, 25 July 2022 (UTC)

RFC on Terpenes
There is a possibly interesting RFC on the Terpene article talk page: Talk:Terpene. The issue is whether it is useful to include WP:MEDRS resources to document the (current) fact that a very widespread theory about terpenes currently has no scientific backup. If this is of any interest to you, feel free to express your opinion there. Finney1234 (talk) 21:20, 26 July 2022 (UTC)

Sulfuric(IV) acid
I've noticed that some time ago names like 'Sulfuric(IV) acid' and 'Sulphuric(IV) acid' were added to this article. Also in Sulfite there is "(or the sulfate(IV) ion, from its correct systematic name)". I would like to know what is the source of these names, and more importantly, which source stated that these names are systematic? AFAIK since 1940 IUPAC never published any publication with such names as systematic.

Why I'm interested: such names are very popular in Polish education system. The reason why such names are used there is not entirely clear, even despite the fact that these were never recommended systematic names (both by IUPAC and Polish Chemical Society) and nowadays it is very hard to fight this misinformation.

I would be very grateful for any authoritative source of such names in English. Wostr (talk) 12:36, 18 August 2022 (UTC)


 * This is sort-of Stock nomenclature that was first included in IUPAC inorganic nomenclature in 1940 and is still present in the latest version, IUPAC nomenclature of inorganic chemistry 2005. But sulfuric acid is a common name so this is mixing common and systematic naming systems. You see it a lot in UK pre-university chemistry courses, probably because they are trying to teach nomenclature but don't want students to have to memorise a huge set of non-systematic names like permanganate. --Ben (talk) 13:30, 18 August 2022 (UTC)


 * Yes, this is some variation of 'Stock nomenclature', but not 'systematic' in any way. E.g. in Red Book 1990 there were names for some oxoacids and derivatives like 'trioxochloric(V) acid' for HClO3 and 'trioxochlorate(V)' for ClO3-, but never 'chloric(V) acid' and 'chlorate(V)'. I am perhaps very strict in this regard, but as I mentioned, it is a big problem in Polish right now (with large discrepancies between the recommended nomenclature and that used in schools), and I was very surprised to see the same in the articles in English and I was convinced that it was mainly a Polish 'invention'. I should then try to look at British textbooks, because in the pl.wiki we have a whole section in respective article about inorganic nomenclature that describes this quasi-systematic nomenclature and why it is not systematic in any way. Wostr (talk) 15:26, 18 August 2022 (UTC)


 * To give you a concrete example, I just checked the textbook they used in my school for A-Level chemistry. On page 206, it outlines proper Stock nomenclature, for example copper(II) chloride. It then moves onto anions and that's where things diverge from the nomenclature a professional chemist would use. There's nitrate(V) for NO3−, chlorate(I) for ClO−, chlorate(III) for ClO2−, chlorate(V) for ClO3− and, chlorate(VII) for ClO4−. Obviously outside of school everyone calls these species nitrate, hypochlorite, chlorite, chlorate and perchlorate. --Ben (talk) 20:07, 18 August 2022 (UTC)
 * Interesting, this would mean that the same type of names are used in education in both countries, but it seems that there is no single source for such names (as if they were created independently in both countries, possibly by shortening the names from Red Book 1990, because there is no authoritative source from which they could be taken). Wostr (talk) 12:37, 20 August 2022 (UTC)

Connected contributor
I've added a connected contributor tag for myself to a chemistry biography article that I wrote back when I was a less experienced editor; see. I would like to invite anyone here to review the article to check its neutrality. After you have done so, feel free to update the tag by adding checked to it. Best, &#123;{u&#124; Sdkb  }&#125;  talk 18:35, 20 August 2022 (UTC)

Requested move at Talk:Lithium battery
There is a requested move discussion at Talk:Lithium battery that may be of interest to members of this WikiProject. Vpab15 (talk) 18:37, 23 August 2022 (UTC)

Formatting of chemical formulae in article text
I've noticed a lot of changes in the formatting of chemical formulae in articles recently, for example this diff. The chem2 template seems very good but I'm less convinced by the &lt;chem> tag because it renders the formula as an image and makes it impossible to find with text search. Do we have a policy on this? Ben (talk) 17:37, 13 September 2022 (UTC)


 * Don't know about policy, but the diff you gave is OK with me: a complicated standout formula (full reaction even; own line) may well use &lt;chem>; and inline (in running text) is used and works nicely. One cannot even  search a simple formula like 14C in wikitext, so other routes ere needed. DePiep (talk) 18:07, 13 September 2022 (UTC)


 * This has been discussed before: Wikipedia_talk:WikiProject_Chemistry/Archive_46. I think that use of &lt;chem> and is deprecated, but this isn't really enforced. Personally I prefer the old fashioned way. --Project Osprey (talk) 23:08, 13 September 2022 (UTC)


 * Yes should be avoided. undefined has now been improved so that you can find the formula with a search, and also copy and paste it (unlike which is more difficult to use anyway). But if you need long arrows with text and symbols above, then you may have to use $$ markup. Graeme Bartlett (talk) 12:25, 14 September 2022 (UTC)

SI Chemical Data
G'day, I've got our lovely Gordon Aylward's 4th edition of SI Chemical Data on my hands. Since it's the 4th edition (which was published 1998), it obviously does not contain any of the new superheavy elements. Now, I just wanted to know, can the data for all the other elements still be considered to be accurate? Regards X-750 List of articles that I have screwed over 04:45, 16 September 2022 (UTC)
 * I suppose you have to check out the references currently in use in articles and see if the references they are using more up-to-date or accurate measurements. But don't trust our articles to have latest info anyway. Graeme Bartlett (talk) 06:07, 16 September 2022 (UTC)
 * Cheers, excellent point about the cross-referencing. X-750 List of articles that I have screwed over 00:08, 17 September 2022 (UTC)
 * What data, rougly, is used from the SI Ch.D.? Can't find a link to Gordon Aylward in there. DePiep (talk) 08:13, 17 September 2022 (UTC)
 * ... Could someone indicate, .. DePiep (talk) 08:14, 17 September 2022 (UTC)
 * Sure, . The book gives the atomic number, weight, density for the element at 25 C (unless indicated otherwise), melting/decomposition/sublimation temperature, boiling temperature, specific heat capacity and thermal conductivity at room temperature, electrical conductivity at 25 C, structure of a solid (rhombohedral, diamond, layer, chain, tetragonal etc), metallic radius/atomic radius, covalent radius, and ionic radius. That's just for the elements. Next there are the inorganic compounds, which it gives formulas, hazards, structure, whether it is a trimer or dimer, molecular weight, colour, density, melting & boiling temps, solubility (grams, anhydrous substance, per 100g water at 25 C, standard enthalpy of formation and Gibbs energy for 1 mole of the substance, standard entropy and molar heat capacity, molar enthalpy of fusion, sublimation and vaporisation, electric dipole moment for molecules in gaseous state, and much much more. You get the gist. Stuff that'd belong in infoboxes. It covers inorganic compounds, organic functional groups, bond lengths, anything you can image. If you need something specific, don't hesitate to flick me a message. X-750 List of articles that I have screwed over 08:27, 17 September 2022 (UTC)
 * Thanks, sort of CRC then. But by "which data is used" I meant "... in this wiki", i.e., in which references? No WP:element links in [] DePiep (talk) 08:39, 17 September 2022 (UTC)
 * Oh right, I see. No, Graeme Bartlett was referring to other articles, like actual chemistry articles, not Gordon Aylward's specific article. Hope this clears it up. X-750 List of articles that I have screwed over 08:43, 17 September 2022 (UTC)
 * Looking at my copy of SI Chemical Data, which is from 1971 some references used by it are up to the same year. But some data is old, eg pH and conductivity of water at different temperatures is from 1926 and 1959. The references used are compilations and other tertiary literature, and not primary publications. But there are a couple of reviews. Checking out some values (density) there are better figures around than in this 2nd edition, but I don't know about your 4th ed. I reckon that data for superheavy elements is not available at all (apart from atomic number and symbol). Graeme Bartlett (talk) 09:41, 17 September 2022 (UTC)

Dakin reaction
I don't have ChemDraw, otherwise I'd tackle this myself. Commons contains several mechanisms for the Dakin reaction, almost all of them contain errors in the use of curly arrows, or just look unprofessional commons:Category:Dakin_reaction. There is also disagreement on the mechanism (epoxide or no expoxide). Project Osprey (talk) 14:25, 4 October 2022 (UTC)


 * A recent review 10.1039/d1nj03300j (which I have access to) has in its scheme 2 essentially the same mechanism as in our article at Dakin oxidation. I could quibble that the diagram we use has more lone-pair electrons shown than most organic chemists would use but I don't see anything actually wrong. Clearly an .svg file would be preferred. I can easily re-do the diagrams for the article but before that perhaps we should continue this discussion on the Talk Page of the article so it will be more accessible to those interested in commenting and better when archived. Mike Turnbull (talk) 15:10, 4 October 2022 (UTC)
 * Stage 2 looks like an elimination to me, but maybe I'm just fussy. --Project Osprey (talk) 15:13, 4 October 2022 (UTC)
 * I see it as a straightforward [1,2] aryl migration. The electrons in the phenyl-to-C bond migrate so that they become bonded to the oxygen that was the nucleophile centre when the peroxide anion attacked the carbonyl group. An elimination reaction would normally involve loss of a proton, which this does not: the proton originally on the carbonyl group ends up in the formyl ester. The product would be a carboxylic acid if elimination had occurred; the whole point of Dakin reactions is that it is not a simple oxidation of aldehyde to acid. Mike Turnbull (talk) 15:32, 4 October 2022 (UTC)
 * I understand what's happening, I just don't think it's depicted very well. --Project Osprey (talk) 15:50, 4 October 2022 (UTC)
 * I agree that while File:Dakin oxidation base-catalyzed mechanism.png looks correct chemically, it's visually confusing that the layout of the H and O around the benzylic carbon change in 2&rarr;3 (and then around that same C change again in 4&rarr;5). DMacks (talk) 16:06, 4 October 2022 (UTC)
 * Based on your comments, I've created an .svg version of the file as File:Dakin oxidation base-catalyzed mechanism.svg. That's how I would draw the reaction but I'm open to suggestions for further improvements. Mike Turnbull (talk) 11:52, 5 October 2022 (UTC)
 * Beautiful! DMacks (talk) 17:26, 5 October 2022 (UTC)
 * That is an improvement. Many thanks --Project Osprey (talk) 22:44, 6 October 2022 (UTC)
 * @Project Osprey I've updated the article including the recent review ref. Do the other diagrams need redoing or can they be left based on the idea that the base-catalysed mechanism is the most important and the others are similar? Mike Turnbull (talk) 17:19, 9 October 2022 (UTC)
 * Sorry, I've posted this and then gone quiet, not very helpful of me... I think the rest is fine. Thanks again for your efforts. --Project Osprey (talk) 10:44, 10 October 2022 (UTC)

Iridium FAR
Hallo, if somebody finds time to save the article from delisting, please help! --Stone (talk) 08:06, 11 October 2022 (UTC)
 * A link too FAR, been running since the start of Sept. --Project Osprey (talk) 10:26, 11 October 2022 (UTC)

Chem equation formatting
I noticed this equation in ketonic decarboxylation:
 * \ce{R}{\color{red}\ce{-C(O)OH}} + \ce{R'}{\color{red}\ce{-C(O)OH}} \longrightarrow \ce{RR'}{\color{red}\ce{C=O}} + \ce{CO2 + H2O}$$

Maybe we can discuss this equation because the editor OlliverWithDoubleL has been very active: --Smokefoot (talk) 17:01, 9 October 2022 (UTC)
 * Isn't there consensus that Chem2 is preferred over &lt;math chem>?
 * The color labeling is inconsistent.


 * See also above. Ben (talk) 17:05, 9 October 2022 (UTC)

Hey all,

With regards to this particular chemical equation, the coloring I added was meant only to highlight the interconversion between the carboxylic acid and ketone groups in the equation, as emphasis. The ketone should be a different color, you're right.

With regards to my preference of &lt;chem> for equations that aren't inline, I should probably have discussed with you all first. I think the chem and chem2 formatting looks great when it's inline with the text; there, the MOS is right that the font change with &lt;chem> would be jarring. But when the reaction equation is in its own line, like the ketonic decarboxylation one above, I think it looks better when the font is different; just like with math formulae elsewhere on Wikipedia, the change in font makes the equation stand out from the rest of the text, and it also blends in nicely with articles that also contain math formulas of the same font. Also, the choice of font is nicer too; in the usual Wikipedia font, it's near impossible to tell a capital I from a lowercase L (I or l), but the &lt;math> and &lt;chem> fonts make it easy. This is important when considering, for instance, the oxidation state of a substance (e.g. I) versus its physical state (e.g. liquid, l). I know that some users have placed links within their formulas, which isn’t possible with &lt;chem>; I’ve tried to move the names of the substances to the surrounding text, or instead named the substance using \overset. Is this acceptable?

Also, and this is just an issue that I have as a primarily mobile user, but I try to turn the formatting of equations like this: chem2 + chem2 -> chem2 + chem2 + …

Into this: … -> … or &lt;chem> … -> … /chem>

Because, although the former may look nice on a desktop browsing window, it is often text-wrapped for mobile users, which creates a lot of confusion particularly when a series of equations is present or when the formulas are particularly long. In that case, a single chem2 or &lt;chem> formula is nice because it ensures the text isn’t wrapped, so I've been collecting both inline and indented formulas into one unbroken chem2 or &lt;chem> line. OlliverWithDoubleL (talk) 18:11, 9 October 2022 (UTC)


 * It looks like there are a range of views here on the &lt;chem>. As there is no consensus to use it and there are some good reasons not to use it (such as not being searchable within the page, unlike chem2), I think it would be best if you stopped adding &lt;chem> tags to articles for now and stuck to chem2. Ben (talk) 12:11, 15 October 2022 (UTC)
 * Thank you Ben. I suspect that the editing community here dislikes &lt;chem>, and prefers the chem2 method or the old &lt;sub> route.  --Smokefoot (talk) 13:41, 15 October 2022 (UTC)


 * For reference: current MOSCHEM guidelines: Manual of Style/Chemistry. Ben (talk) 13:43, 15 October 2022 (UTC)

Historic benzene structures
It would be good to also have all historic benzene structures as they appeared in the original publication. If not in the article itself, then at least on Commons. Currently, it seems that we only have two of them:

The relevant original publications of the others need to be identified. Any help is much appreciated. --Leyo 13:50, 20 October 2022 (UTC)


 * The references in the caption for the diagram at Benzene include good links to archival material including this Berichte reference from 1867. They would be out of copyright, of course. Mike Turnbull (talk) 15:10, 20 October 2022 (UTC)
 * Thank you. Before, I tried to find the structure proposed by Dewar as it appears in our article. However, it is not contained in reference cited there.
 * I extracted and uploaded the proposal by Claus. Moreover, I created c:Category:Historic benzene structures. --Leyo 22:04, 20 October 2022 (UTC)
 * Dewar was hedging his bets. He drew (p. 85 of 10.1017/S0370164600045387) seven possible structures based on C6H6, some of which are fanciful indeed. However, he included (middle of top row) what we would now consider to be the "correct" structure and to the right on the second row what we now call Dewar benzene. Mike Turnbull (talk) 10:05, 21 October 2022 (UTC)
 * Thank you. I had been looking for a more standard structural formula. :-)
 * By the way: In the article, it says that Dewar's publication is from 1867, but it seems that 1869 is correct. --Leyo 12:40, 21 October 2022 (UTC)
 * I've corrected them in the two relevant articles. The confusion arose, I think, because the 1869 publication was describing Sessions run in 1866-67. Mike Turnbull (talk) 16:57, 21 October 2022 (UTC)
 * Thank you.
 * I just wanted to note that the table in de.wikipedia (that corresponds to Benzene) now shows consistently the historic structural formulas. This might also be done here. --Leyo 21:34, 21 October 2022 (UTC)
 * I suggest you go ahead and be WP:BOLD and make that change, which personally I would take to be an improvement. Mike Turnbull (talk) 10:29, 22 October 2022 (UTC)
 * Okay, thanks. Done. The following two sentences from previous image caption didn't fit anywhere:
 * --Leyo 21:14, 22 October 2022 (UTC)
 * --Leyo 21:14, 22 October 2022 (UTC)

Hantz reactions
de:wp is currently discussing the deletion of Hantz-Reaktionen, because the name is OR. Earlier a renaming was discussed with no result. Can anyone contribute to this topic? Gimli21 (talk) 12:18, 7 November 2022 (UTC)

Flavanones/Flavones
Would I be correct in thinking that Category:Flavanones and Category:Flavones (and their associated wikimedia pages) should just be merged? Project Osprey (talk) 15:23, 17 November 2022 (UTC)


 * Probably not. The parent flavone has an unsaturated oxygen ring (see Chemspider entry), whereas flavanone is partially saturated in that ring, as for its record. Of course, I haven't checked that the categorisations on all our articles are correct. Mike Turnbull (talk) 15:58, 17 November 2022 (UTC)
 * I don't know how I missed that. Cheers --Project Osprey (talk) 16:03, 17 November 2022 (UTC)

Another reason to be on guard against student assigned to writing Wikipedia articles
Aside from the fact that their contributions are usually poor and their supervisors do not supervise. https://twitter.com/RetractionWatch/status/1592321603689484288/photo/1 --Smokefoot (talk) 02:26, 15 November 2022 (UTC)


 * Worth reading. DePiep (talk) 07:50, 15 November 2022 (UTC)


 * I've passed the link onto The Signpost (hope you don't mind). Anecdotally we know it to be true, but it's interesting to see how big the effect is. --Project Osprey (talk) 22:12, 15 November 2022 (UTC)
 * I think this was already covered in Signpost a few months ago. It proved some authors are copying Wikipedia without credit. Graeme Bartlett (talk) 06:06, 16 November 2022 (UTC)
 * Bits of it did seems familiar... mayhaps they borrowed content from a Signpost article to write their blog post, and I've now sent that blog back to Signpost? Great example of circular referencing, if thats the case. That is something which does concern me. Remember that book on inorganic compounds that someone (Smokefoot?) found, which lifted whole sections from Wikipedia without credit. --Project Osprey (talk) 10:05, 16 November 2022 (UTC)

School projects

 * And if you do want to get stuck into some student work, there is a bunch of maingroup chemistry pages arriving in the last week: Boraacenes, Phosphorus porphyrin, Borepin, Magnesium(I) dimer, 1-phosphaallenes, N-Heterocyclic carbene boryl anion, ?m-Terphenyl. We appear to get a batch once a year. Graeme Bartlett (talk) 11:50, 16 November 2022 (UTC)
 * The main group stuff is probably the work of MIT students. They steadfastly ignore guidelines, producing very specialized but usually technically correct articles, sometimes sprinkled with their own (DFT calculations.--Smokefoot (talk) 13:44, 16 November 2022 (UTC)
 * Wiki Ed/Umiversity of Alabama at Birmingham/Honors Organic Chemistry I (Fall 2022) is landing a lot of their work in mainspace this week. Spot-checking, it often needs better integration/reduced redundancy/tightening to the article's specific topic (as usual, adding a content block to an existing encyclopedia article rather than writing a self-contained school essay from scratch). But content-wise seems generally sensible. And they're often working on a reasonable academic level of the content. DMacks (talk) 16:49, 17 November 2022 (UTC)

Merger discussion for Alpha and beta carbon
An article that you have been involved in editing&mdash;Alpha and beta carbon&mdash;has been proposed for merging with another article. If you are interested, please participate in the merger discussion. Thank you. Mdewman6 (talk) 02:48, 21 November 2022 (UTC)

Polybutadiene acrylonitrile
Could a (general) structural formula be added? And what about adding the chembox? Leyo 08:35, 22 November 2022 (UTC)
 * I have added a chembox. There seems to be different substance ids depending how this is terminated. For polymers most representations are a failure, and databases do not record then correctly. Graeme Bartlett (talk) 09:48, 22 November 2022 (UTC)
 * Going by the name I'm unsure how it's different from Acrylonitrile Butadiene Rubber... The article said that it includes acrylic acid (but it's not in the name, so, low levels?) but that is also a type of acrylonitrile butadiene rubber (XNBR). --Project Osprey (talk) 12:08, 22 November 2022 (UTC)
 * Yes, they look to be the same as the ids look the same as for Nitrile rubber. Graeme Bartlett (talk) 21:17, 22 November 2022 (UTC)
 * I'm guessing there must be a difference in the structure. The stated uses of the 2 materials are very different. IDs aren't always useful that useful for polymers, lots of things get lumped together. --Project Osprey (talk) 10:43, 23 November 2022 (UTC)
 * as i've figured out through some NASA paper, PBAN and HTPB are the liquid prepolymers, the "finished" product is a rubbery substance (like NBR or XNBR).
 * https://www.ibb.ch/publication/NASA-SP/sp8075.pdf https://ntrs.nasa.gov/citations/19660025411 this is especially true in publications from around 1955 to 1965 +/- when PBAA, PBAN, CTPB and HTBP were invented and basically always refered as the prepolymer used in mixing solid rocket fuel, if you take later publications, you'll get a more mixed/synonymous use with the cured Butadiene Rubber Type polymers --Suit (talk) 12:49, 24 November 2022 (UTC)

Hydroxyl-terminated polybutadiene
Shouldn't the structural formula in this article have terminal hydroxyl groups? The first sentence reads as follows:
 * Hydroxyl-terminated polybutadiene (HTPB) is an oligomer of butadiene terminated at each end with a hydroxyl functional group.

If yes, is anyone able to amend that structural formula? Leyo 22:52, 18 November 2022 (UTC)
 * Good catch. It does seem that OH groups should be shown, sorta the defining feature. If I get time after some vacation travel, I will redraw if no one else does.--Smokefoot (talk) 04:13, 19 November 2022 (UTC)
 * The article needs a bit of work. The main reference to a crayvalley .pdf is no longer working and needs to be found at the Wayback machine. The external link for US5159123 goes to that archive rather than a live Google Patents link such as this one. Having read the patent, I'm not really any wiser as to the exact structure! The wiggly lines in the current diagram in the article just refer to an unspecified total number of repeat units, without, as notes, actually showing where the OH groups would sit. From the patent's description of the synthesis, I think they will be somewhat at random throughout the structure, many more than two per polymer molecule. Mike Turnbull (talk) 11:11, 19 November 2022 (UTC)
 * Thanks for looking into it.
 * On https://www.crayvalley.com/products/liquid-polybutadienes/poly-bd-hydroxyl-terminated/, the link to the TDS does not work. --Leyo 20:56, 19 November 2022 (UTC)
 * On that page, the Tech Update" link gets to a PDF that has the structure of Poly bd R45HTLO. DMacks (talk) 21:33, 19 November 2022 (UTC)
 * @DMacks I tried that link yesterday, like Leyo, and it did nothing (i.e. it just refreshed the page I was on). It's doing the same today, perhaps because my IP address is in the UK. Can you put the new link into the Wayback machine and get it copied there? For me, copying the link gives https://www.crayvalley.com/products/liquid-polybutadienes/poly-bd-hydroxyl-terminated/# (note the hash symbol), not a .pdf. Mike Turnbull (talk) 13:41, 20 November 2022 (UTC)
 * need to mention Wikipedia_talk:WikiProject_Chemistry here, HTPB (and PBAN) used in solid rocket fuel referred to the liquid prepolymer in the past, the cured polymer would bei an rubber like XNBR - this needs to be crosschecked with some expert on the topic --Suit (talk) 12:53, 24 November 2022 (UTC)

Molar attenuation coefficient
Never heard of "mass attenuation coefficient"? Me either. But that is the term imposed by the speech police at Wikipedia for what mortals call "extinction coefficient". I recommend that we move Mass attenuation coefficient to extinction coefficient. Comments? --Smokefoot (talk) 21:41, 28 November 2022 (UTC)
 * Mass attenuation coefficient seems to be about xrays... did you mean molar attenuation coefficient? (also weird to me) --Project Osprey (talk) 22:11, 28 November 2022 (UTC)
 * Yes, its molar attenuation coefficient that has me bothered. Thanks, --Smokefoot (talk) 22:50, 28 November 2022 (UTC)
 * So, Proposal: move molar attenuation coefficient to  -DePiep (talk) 12:49, 29 November 2022 (UTC)


 * Move to molar absorption coefficient. I was quite surprised that this important and common concept has been at this obscure synonym for so long. I learned it as molar absorptivity or molar extinction coefficient. Just extinction coefficient is properly a disambiguation page to disambiguate the chemical (mole units) and physics (mass units) uses of the term. Mdewman6 (talk) 01:36, 29 November 2022 (UTC)
 * Support move to molar absorption coefficient. I wonder if we can get some help? --Smokefoot (talk) 12:36, 29 November 2022 (UTC)
 * Support seems the best outcome --Project Osprey (talk) 14:22, 29 November 2022 (UTC)
 * Support I have just consulted the indexes of 2 phys chem textbooks (Atkins + de Paula, Engel + Reid) and 2 molecular spectroscopy textbooks (Banwell + McCash, Hollas). All have "molar absorption coefficient". None has "molar attenuation coefficient". Dirac66 (talk) 17:19, 29 November 2022 (UTC)
 * Support. Even if attenuation is the name of the effect itself (Attenuation coefficient, or lay-language sense of attenuation) and even if Molar attenuation coefficient is a known phrase for this specific situation (note: I don't see evidence of this at all(?) let alone commonly), it does not seem to be the WP:COMMONNAME. DMacks (talk) 18:18, 30 November 2022 (UTC)
 * Support This search on IUPAC/degruyter for "molar absorption" shows it is the most commonly used term. The alternative search in the same database for "molar attenuation" gets hits but not with the two words together. Mike Turnbull (talk) 11:29, 1 December 2022 (UTC)
 * Can someone else other than me make this move? I seem to screw up such moves often. And I dont have the rights to move molar attenuation coefficient to molar absorption coefficient.--Smokefoot (talk) 19:42, 1 December 2022 (UTC)
 * I can do it, though it might be better if an admin G6's it rather than me doing page swap. Also, though this isn't an RM, it might be best to wait 7 days since this was such a long standing title, just to make sure we have clear consensus. Mdewman6 (talk) 19:45, 1 December 2022 (UTC)
 * I can do it, but will refrain since I participated in the discussion. I agree no harm in treating this as an informal RM-like situation. In a few days, post a note to WP:RM and someone external can figure out the best set of buttons to push to make it happen. DMacks (talk) 19:59, 1 December 2022 (UTC)
 * I think we can bypass the WP:INVOLVED aspect of a normal RM (see WP:RMCI) so long as it remains unanimous- taking it to TR implies it is not controversial anyway. I will complete the move once 7 days have elapsed since the initial comment (unless someone objects or completes the move first). Mdewman6 (talk) 20:19, 1 December 2022 (UTC)
 * WP:RM best. Always gave me good cooperative editors & clean editing (although A.A. is no longer there). DePiep (talk) 20:30, 1 December 2022 (UTC)
 * TR just means you need a page mover or admin to complete an uncontroversial move you can't complete yourself, but we have several page movers/admins here already. Mdewman6 (talk) 20:38, 1 December 2022 (UTC)

Recent edits to Dorothy Hodgkin
Please see Talk:Dorothy Hodgkin. -- Red rose64 &#x1f339; (talk) 21:18, 7 December 2022 (UTC)

Splitting discussion for Zinc oxide


An article that been involved with ( Zinc oxide ) has content that is proposed to be removed and moved to another article (Zinc white). If you are interested, please visit the discussion. Thank you. AngusW🐶🐶F ( bark  •  sniff ) 17:34, 30 December 2022 (UTC)