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Requested move at Talk:Per- and polyfluoroalkyl substances/Archive 1#Requested move 24 May 2023

There is a requested move discussion at Talk:Per- and polyfluoroalkyl substances/Archive 1#Requested move 24 May 2023 that may be of interest to members of this WikiProject. ModernDayTrilobite (talk • contribs) 14:52, 31 May 2023 (UTC)

Maria Bakunin

Hi everyone! As part of the Women in Green edit-a-thon, I recently undertook the improvement of the article on Maria Bakunin. I think I've done rather well at providing biographical information on her, but I've unfortunately hit my limit in terms of my research capabilities. While I'm able to read Italian, I'm not nearly as well-versed in chemistry or chemical terminology, so my head gets a bit scrambled when I go over sources that are jargon-heavy. Would anybody here be willing and able to help with this article? From what I've read, Bakunin seemed like a very interesting and influential figure in chemistry, and the encyclopedia would do well to have a good write-up on her. -- Grnrchst (talk) 14:54, 15 June 2023 (UTC)

@Grnrchst I've wikilinked ichthyol to the correct chemistry. I presume that's the sort of terminology you don't know. The best place for specific questions would be at Talk:Maria Bakunin, where I or other chemists will try to help. My Italian is poor and limited to what Google translate provides! I don't have access to most of the sources you have used. Mike Turnbull (talk) 15:16, 15 June 2023 (UTC)

Ernest Rutherford

The page Ernest Rutherford has been updated to more fully include the details of his life and scientific work. The page now expands upon his educational biography, appends dates to several of his discoveries, and includes others which had previously been omitted. I have also made a handful of additional edits on miscellaneous other sections. This may (or may not) be of interest in (re-)evaluating your project's content assessment of the article. Doughbo (talk) 01:20, 13 June 2023 (UTC)

@Doughbo The article is already rated "B" by most projects. To take it higher you would need to initiate a formal GA assessment. See WP:GOOD. Note that GA lies below the now rarely-used A (see WP:ASSESS). Mike Turnbull (talk) 15:23, 15 June 2023 (UTC)

General Chemistry template

Hi. We have a template {{Branches of chemistry}} that collects many related subfields of chemistry, I suggested to turn it into a more general one. See related discussion here: Template talk:Branches of chemistry#Turn this into a general Chemistry template. I also would like to point out that template fails to link fundamental chemistry concepts like Elements, Atom, and Bonds in organized fashion. Currently it's linked from See also subsection. Weirdly enough. Please pay attention. Thank you. AXONOV (talk) ⚑ 17:28, 11 July 2023 (UTC)

Importing free content rather than writing it from scratch

Example: From this thesis, the articles Proteolipid, Peptide amphiphile, Peptide therapeutics and Hydrogel were amended.

Hello, everyone! I'd like to discuss and advocate the concept of importing free content rather than writing it from scratch. I can only assume that the internet hosts an order of magnitude more high-quality free content than our capacity to produce such texts.

To illustrate this idea, I began by inserting the theoretical portion of my PhD thesis into the English Wikipedia (see polyester). Apparently, it made a positive impression: After a few weeks, someone translated the text and images into the Arabic Wikipedia. There are countless other freely available theoretical parts of theses that could be suitable for import into Wikipedia.You can find more ideas on this topic at User:Minihaa/Incorporation of doctoral theses.

I am genuinely surprised that not many others have utilized this tremendous potential of high-quality texts. I would love to promote and discuss my idea further. We are currently overlooking a tremendous potential, in my opinion. Minihaa (talk) 06:50, 24 July 2023 (UTC)

If the material is suitable, then it would be good. But the style of writing is probably wrong, this is an encyclopedia, written so that English speakers from year 12 could understand it. Not many PhD theses would be suitable, even if copyright permitted reuse here. Images are more likely to be useful. Graeme Bartlett (talk) 07:42, 24 July 2023 (UTC)

Also note CC BY-SA 4.0 is now a usable licence.

I am inclined to agree with Graeme Bartlett - academic articles and PhDs are not written in the same way as encyclopedia articles, e.g using way too much jargon and too many details that don't really belong in an encyclopedia article. I think most such text, even if suitably licenced, would be unsuitable for Wikipedia. Jo-Jo Eumerus (talk) 08:56, 24 July 2023 (UTC)

Thanks for your judgement! In my view, the writing style is in about half the theses adequately simple enough. Let me provide you with two examples: The article on Polyester#Synthesis is written fairly simply, and it is a topic of general public interest. On the other hand, the text on the Nitro-Mannich reaction is as complex as any typical organic chemistry textbook, but it addresses a topic that is primarily of interest to experts (it would be challenging to explain the concepts to 12-year-olds). Minihaa (talk) 09:52, 24 July 2023 (UTC)

I also am very skeptical of importing much from any thesis. This view does not detract from the noble effort that writing such documents entails.

Of course, the thesis writer is convinced of their insights and purview, but fresh PhDs are IMHO usually ill-equipped for extensive Wiki writing. The problem is that many thesis authors are convinced otherwise. Facts: few theses are ever cited in the real world and they are all unrefereed. Sometimes theses have refs that are very useful, I agree . But the last thing we want to deal with here is extensive importation of thesis prose. --Smokefoot (talk) 11:19, 24 July 2023 (UTC)

Note: What user:Graeme Bartlett said, English speakers from year 12 is not the same as what user:Minihaa said, 12-year-olds. Year 12’s are 17-18 years old. YBG (talk) 11:38, 24 July 2023 (UTC)

@Smokefoot: I understand that you are worried about extensive importation. But could you elaborate on where you see the problem with theses in general? "unrefereed" applies to any other wikipedia article. Minihaa (talk) 20:18, 24 July 2023 (UTC)

The minimum standard for reliable sources for Chemistry articles means peer review, just like most journal articles: referees, usually anonymous, filter out the good, bad, and the ugly prior to publication. Wikipedia actually prefers a higher level of where the peer-reviewed work is further evaluated prior to inclusion in a review (WP:SECONDARY) or book (a review of reviews often, WP:TERTIARY). Theses are basically self-published documents that are written with good intentions, but the thesis reviewing process is not as rigorous as peer review. So, yes, I am slightly worried by the prospect that lots of thesis content would slide into Wikipedia. Theses can contain some extremely useful summaries, indeed. One, however, has to be pretty selective in picking the parts of the theses and which thesis. Most specifically, I object to citing theses as a sources. They can be sources of sources, but they don't meet the standard of WP:RS, IMHO.

A specific comment above that caught my eye and worries me is this "freely available theoretical parts of theses". Even if they followed WP:SECONDARY, theorists could flood most articles in Wiki Chem with content that could be very damaging (tangential, diluting). WP-Chem is not prepared for this onslaught. Imagine this: every compound article would have a DFT section of orbitals and energies, every reaction article would have a potential energy surface, etc. So far so good though.

Overall, WP-Chem is in pretty good shape. We are refining a good core of articles. It is ideas like yours, if implemented selectively, that could make the project even stronger. The key is selectivity. End of bloviation,--Smokefoot (talk) 21:27, 24 July 2023 (UTC)

@Smokefoot: Thank you very much for the detailed comment. I essentially agree! Selectively choosing appropriate text is clearly highly significant, and we should avoid "diluting" good and relevant articles with information that is only relevant to a few experts. I was not suggesting using theses as a source but rather their summaries of peer-reviewed research. I know and agree that primary research must be used cautiously (WP:RSPRIMARY). Selecting appropriate material requires a considerable effort; thus, I don't see much risk of anyone conducting mass imports when adhering to these rules and common sense.

I will add the essential thoughts of the comments so far to my user page in case anyone should be interested in importing free material. Thanks to everyone so far; your thoughts are much appreciated. Minihaa (talk) 09:41, 26 July 2023 (UTC)

A tool to monitor and improve images in this Wikiproject

Hi there! I am not part of this Wikiproject, but I am a Wikigraphist. I am interested in improving Wikipedia’s visual content and I built a tool that could help detect visual gaps in Wikiprojects.

I called it Visual Content Assessment Tool, or simply VCAT.

A working version of VCAT with data for Wikiproject Neuroscience already extracted by me on 26/07/2023 can be found at VCAT-dashboard. You can always extract fresh data for any Wikiproject using the extraction tool, a command line tool I created for this purpose.

Some of the actions you can do with this tool are:

• Monitoring the visual content coverage in a Wikiproject
• Detecting articles needing images (eg. articles without images)
• Detecting low resolution images to improve (eg. raster diagrams to be vectorized)

Then you can ask for image creation or vectorization on the Graphics Lab.

What do you think? Could it be a useful tool? MingoBerlingo (talk) 16:04, 26 July 2023 (UTC)

Bonding in organophosphates

Is the bonding in organophosphates (and other P(V) compounds) explained entirely by hybridisation with the 3S orbital? I occasionally see the P=O drawn as being dative or a (RO)₃P⁺−O⁻ ylide doi:10.1002/chem.201806247, with the shortened bond being explained by ionic attraction. P(IV) does seems to be a real thing, so maybe that's valid (doesn't seem right though). I also don't understand why species like (RO)₅P are so rare, you wouldn't naturally expect hybridisation with s-orbitals to preference the formation of pi-bonds. I can't find any good sources which discuss this, anyone got any pointers? Project Osprey (talk) 09:55, 30 July 2023 (UTC)

C, P and other main group elements are endowed with four valence orbitals, period. These elements must make do with these four atomic orbitals (poor things). 3-center, 4 electron bonds are usually invoked for species like PF₅ and [PF₆]^-.

• 159 compounds of the type P(OR)_x (x≥5) are listed in the Cambridge Crystallographic Database, starting with P(Ocyclohexyl)5 (doi 0.1107/S1600536801015951). Most have quite electronegative substituents on O. For example TRISPHAT. My guess is that the alkoxyl derivatives are prone to Arbuzov reaction whereby nucleophiles attack carbon, leading to phosphates.
• PBr₇ seems to be animpossible compound until one realizes that it is the Br₃^- salt of fairly routine PBr₄⁺.--Smokefoot (talk) 13:32, 30 July 2023 (UTC)

I understand that less well than I should. Three-center four-electron bonds confuse me, as most descriptions rapidly descend into pure maths, which I have trouble following. Why are phosphonium ylides dipolar but phosphates not? You did however give me some leads which lead to this paper doi:10.1039/c3cc45204b, which is somewhat more narrative. --Project Osprey (talk) 20:07, 30 July 2023 (UTC)

Spammer?

I am very distracted these days, but my guess is that user:NASH Obesity is a ref spammer.--Smokefoot (talk) 12:46, 27 July 2023 (UTC)

I've added an initial comment on their Talk Page. Mike Turnbull (talk) 19:27, 28 July 2023 (UTC)

.... which seems to have done some good. Mike Turnbull (talk) 10:42, 31 July 2023 (UTC)

I would be surprised. Ref spammers are unctuous when caught in the act, but the goal doesnt change: Ref my (usually specialized) papers, ref my (usually specialized) papers, and ref my (usually specialized) papers. The remedy is delete the pollution.--Smokefoot (talk) 12:14, 31 July 2023 (UTC)

Credibility bot

As this is a highly active WikiProject, I would like to introduce you to Credibility bot. This is a bot that makes it easier to track source usage across articles through automated reports and alerts. We piloted this approach at Wikipedia:Vaccine safety and we want to offer it to any subject area or domain. We need your support to demonstrate demand for this toolkit. If you have a desire for this functionality, or would like to leave other feedback, please endorse the tool or comment at WP:CREDBOT. Thanks! Harej (talk) 18:12, 5 August 2023 (UTC)

Article naming: ideas needed

The double bond rule article covers two unrelated concepts with this name:

1. Multiple-bonding among certain elements
2. Carbon–halogen bonding adjacent to pi bonds

so I plan to WP:SPLIT it into two separate articles. In order to disambiguate them, I need different names, either actually different terms or a parenthetical for one or both to clarify each's topic. So...what should I call them? Given the current content, meaning #1 is larger and the original meaning here, so my first thought is to offload #2 into a new name. "Double bond rule (allylic reactivity)" seems pretty clear, but the topic is not strictly limited to allylic. Or #1 could go to "Double bond rule (multiple-bonding)", but that sounds redundant or maybe even contradictory if one reads the article. Not a big deal, but if anyone has any thoughts I'd love to hear before proceding. DMacks (talk) 03:12, 7 August 2023 (UTC)

Never heard of these in either context; but a brief browse of Google Scholar implies that discussions around 'Multiple-bonding' should win out. The increased reactivity of the allyl group is discussed at allyl group. I would suggest merging the second section in there. Leave a 'see also' note on the 'double bond rule' page to chatch anyone who gets lost. --Project Osprey (talk) 09:33, 7 August 2023 (UTC)

I agree with Project Osprey. Even the first usage is debatable if the "rule" has "numerous violations" as the lead says. The concept that sigma-bonded C-halogen is "very stable" but an allylic one is "very reactive" is, IMO, misleading given that iodomethane is a standard methylating agent. Mike Turnbull (talk) 12:16, 7 August 2023 (UTC)

Maybe the C-halogen rule could be "Schmidt's Double Bond Rule" or maybe it could just redirect into allyl. I think that it is archaic. That rule was developed in the 1800's when bonding theory was primitive but then again the J Chem Ed article gives a nice analysis of this theme. The double-bond rule for main group elements, while liked by me, is obscure based on these findings:

• IUPAC Gold Book: no mention

• ChemAbs search gave 30 articles, one of which is related to enediols in connection to sugar chem

• March (organic "bible"): no mention
• Greenwood and Earnshaw (inorg "bible"): no mention
• Chemical Reviews: one lightly cited review "The Mechanism of Some Important Organic Reactions" Otto. Schmidt, the coiner of one of the Double Bond Rule for C-halogen bonds.

Reflecting the Euro-inclination toward main group chem, Chem Soc Rev. and ACIE have several articles that cite the rule. Some of many examples:

• "Only in 1976 was the ‘Double-Bond Rule’ disproved, with the publication of the first heavier MG multiple bond described by M. F. Lappert, in [{(Me3Si)2CH}2Sn]2. This was soon followed by related low-valent Si^II and P^I compounds (viz. [{(Mes)2Si}2] and [{(Mes*)2P}2]..."
• "Thirdly, heavier main group elements are reluctant to form multiple bonds, as recognized early on by Pitzer and Mulliken,6 and usually referred to as the double-bond rule."
• "...In the case of Si6H6, not the benzene structure (with “double bonds”) but rather the prismane structure with single bonds is preferred"

My three cents, --Smokefoot (talk) 13:13, 7 August 2023 (UTC)

Fire Diamond in Chembox needs Allignment

Hi, it seems like the fire diamond in Chembox template for all chemical compounds is mis-allingned. I can't fix it (as I have no idea how it works). Can anyone having knowledge about it help? Thanks in advance!! Ray Frost (talk) 06:29, 9 August 2023 (UTC)

@Ray Frost Can you be more specific about what you think is wrong? Looking at benzene as an example, its fire diamond looks perfect to me (on a PC screen), with the horizontal positioning central in its box and the vertical position with just a few pixels of space above/below. Mike Turnbull (talk) 11:10, 9 August 2023 (UTC)

it is completely offset to the right on mobile devices...with some numbers/ letters overlapping the image borders. I have checked on multiple mobile devices all with latest version of chrome Ray Frost (talk) 12:07, 9 August 2023 (UTC)

Sorry, I have no idea about how mobiles may differ but I do know that there's an app or you can use a browser directly. Maybe this is something to raise at WP:VPT? The essay User:Cullen328/Smartphone editing may suggest something to you. Mike Turnbull (talk) 14:01, 9 August 2023 (UTC)

User:DePiep has been banned again. Not sure when he'll be back to sort this. --Project Osprey (talk) 14:07, 9 August 2023 (UTC)

He was banned indefinitely in May '23. He can appeal after a year. Mike Turnbull (talk) 14:18, 9 August 2023 (UTC)

It looks fine on mobile in chrome and firefox mobile view, so Ray, what are you using to get the problem? Graeme Bartlett (talk) 00:09, 26 August 2023 (UTC)

The issue was resolved,

I'm so sorry for not updating this in the discussion, but this issue was solved by TheDJ, Jonesey95 and others at WP:VPT on 11th August, 2023. I was recommended for the same by @Michael D. Turnbull, so I thought the discussion here was over. The discussions (Titled: Fire Diamond Alignment in Chembox Template) of the same at WP:VPT have now been archived (click here to view). Ray Frost (talk) 12:31, 26 August 2023 (UTC)

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

There is a requested move discussion at Talk:Β-Butyrolactone#Requested move 16 August 2023 that may be of interest to members of this WikiProject. —usernamekiran (talk) 17:26, 2 September 2023 (UTC)

X-ray nanochemistry nomination for deletion.

I have nominated it for deletion as it appears to be one author reinventing under a new name effects of x-ray damage. Please comment as appropriate. Ldm1954 (talk) 22:48, 27 November 2023 (UTC)

Requested move at Talk:Monounsaturated fat#Requested move 10 August 2023

There is a requested move discussion at Talk:Monounsaturated fat#Requested move 10 August 2023 that may be of interest to members of this WikiProject, such as those who would like to offer their knowledge on the chemistry of fats vs. fatty acids. Rotideypoc41352 (talk · contribs) 22:28, 25 August 2023 (UTC)

Please see also a separate but related move request at Talk:Polyunsaturated fatty acid#Requested move 31 August 2023. Rotideypoc41352 (talk · contribs) 02:53, 7 September 2023 (UTC)

Branching (polymer chemistry)

Branching (chemistry) (the pre-2010 article title) was left to redirect post-move to Branching (polymer chemistry) until retargeted to Branch (disambiguation) as {{R from incomplete disambiguation}} by DMacks in 2021, because at that time there were 2 other chemical concepts listed there in addition: branched-chain amino acid and branched alkane. However, recently the dab page was split to create Branching and these other topics were removed as partial title matches altogether (and we also have branched-chain fatty acid and other PTMs too). I considered a requested move to move the article back to the shorter disambiguation as the main article for "branching" in a chemistry context, but this all caused me to realize that that article really does focus on branching of polymers and not the more general organic chemistry concept of branched versus unbranched chains. I'm not sure we have a single place where Branching (organic chemistry) could be redirected. The closest would seem to be pendant group, but again, that is more about polymers than simple organic compounds. We have straight-chain compound (a redirect to Open-chain compound) where branched-chain compound and branching could be defined. Note that branched-chain redirects to branching (polymer chemistry). Anyway, looking for input on what to do with Branching (chemistry). Mdewman6 (talk) 00:29, 8 September 2023 (UTC)

This may be one of those fuzzy topics where you will need to continue to take the initiative because there are few experts and few advocates.

The topic is handled in alkane as you indicate. March's 6th edition uses "branched" and related adjectives 61x. There are two sections where the term is used repeatedly:

• p. 478: "Branching at the α and β Carbons. For the SN2 mechanism, branching at either the α or the β carbon decreases the rate."
• p1503 "Effect on Elimination versus Substitution.... branching increases elimination ...as a branching increases, there are usually more hydrogens for the base to attack. The other is that a branching presents steric hindrance to attack of the base at the carbon. ... increased α branching also increases the amount of elimination (E1 vs. SN1),...Branching also increases the amount of E2 elimination ... branching favors elimination over substitution,...leaving groups are slowed by β branching."

These excerpts suggest that we should somewhere define α and β branches.

Good luck. --Smokefoot (talk) 03:05, 8 September 2023 (UTC)

@Mdewman6 The IUPAC Blue book may (or may not!) help. "Branch" is mentioned 13 times in this introductory chapter. As Smokefoot, I'd be happy for you take the initiative here and maybe just be bold, reporting back here on what you conclude in case someone objects. Mike Turnbull (talk) 11:29, 8 September 2023 (UTC)

Removal of Influences/influenced from the scientist infobox

hey, here's a proposal to remove Influences/influenced fields from the scientist infobox. It was done for the philosopher infobox, and bacause these fields often have too many unsourced / unnecessary entries never covered in text it might be a good idea for scientists as well. Please see and comment there: Template_talk:Infobox_scientist#Influences/influenced. Artem.G (talk) 16:36, 14 September 2023 (UTC)

Heads-up regarding Richard Ropp

• Ropp, Richard C. (2013). Encyclopedia of the alkaline earth compounds. Amsterdam: Elsevier. ISBN 978-0-444-59550-8.

Well, we've got pages on alkaline earth compounds, and some of them have been crying out for cites for years. Sounds like just the ticket, right?

But you start reading, and then you realize

1. He can't be bothered to cite his sources (OK, fine, it's a pop-sci text, not an academic work)
2. Every now and then, he so mangles a paragraph that it's obvious he doesn't understand what he's talking about and
3. Parts of our pages keep on being word-for-word identical to his text.

Worse, some of the identical text predates the copyright on his book. I don't think it's a COPYVIO problem; I think it's citogenesis and plagiarism.

I've gone through and removed almost every citation to his "encyclopedia" from our pages (one remaining is for picture credit and the other is about terminology, for which he is a debatably-reliable source). I haven't bothered to check whether the removed cites supported content that post-dates his copyright (although if he plagiarized us, whom else has he plagiarized?).

Also, some well-intentioned novice might come along and try to cite him again. So here's a friendly request to keep an eye out for anyone citing him, and kindly let them know that his "work" is actually useless.

Thanks, Bernanke's Crossbow (talk) 06:47, 25 September 2023 (UTC)

It looks like Barium ferrate and Periodate already cite that. Also, Elsevier should know that it's not a good look to copy text from Wikipedia. Jo-Jo Eumerus (talk) 08:07, 25 September 2023 (UTC)

@Jo-Jo: Yes, those are the two I left in place. Bernanke's Crossbow (talk) 16:45, 25 September 2023 (UTC)

We came across this reference for Wikipedia:Articles for deletion/Beryllium chlorate where I discovered it was riddled with errors. Graeme Bartlett (talk) 12:35, 25 September 2023 (UTC)

Ah. Then I guess I'm just late to the party. Bernanke's Crossbow (talk) 16:45, 25 September 2023 (UTC)

Aldol is problematic

Student editors are being assigned topics for the fall where they are required to contribute to Wiki-Chem. One recent assignment is to "aldol". Here is our inventory on that specific topic:

• Aldol reaction. "The aldol reaction (aldol addition) is a reaction that combines two carbonyl compounds (aldehydes or ketones) to form a new β-hydroxy carbonyl compound..."
• Aldol condensation. "An aldol condensation is a condensation reaction in organic chemistry in which two carbonyl moieties (of aldehydes or ketones) react to form a β-hydroxyaldehyde or β-hydroxyketone ..."
• Aldol reactions ("Not to be confused with Aldol reactions"!) "In organic chemistry, aldol reactions are acid- or base-catalyzed reactions of aldehydes or ketones...."
• Aldol "In organic chemistry, an aldol describes a structural motif consisting of a 3-hydroxy ketone or 3-hydroxyaldehyde..."

Then there are various subthemes, including Mukaiyama aldol reaction. Its a problem.--Smokefoot (talk) 13:55, 30 September 2023 (UTC)

I agree the proliferation of articles with similar scope and titles is a problem: we discussed this an Talk:Aldol reaction a few months ago, when User:LoomCreek made a proposal (which didn't reach a consensus) based partly on what other-language versions of Wikipedia were doing. Is this a case where we could get the student editors to do something useful? Apart from updating the articles, they could be encouraged to properly define the WP:COMMONNAME and scope of the articles we should keep and split/merge accordingly. Whatever is done needs to be done carefully so as not to make things worse, so the students' supervisors need to be made aware of the issue. Mike Turnbull (talk) 14:20, 30 September 2023 (UTC)

I also agree there is a problem here; perhaps having the topic covered in all of these separate articles is warranted, but as is typical, the content forking is not properly in place, and the articles are not properly differentiated from each other- the current lede of aldol reactions is especially troubling vis à vis aldol reaction from which it was split. My gut reaction is that aldol reactions should be merged back to aldol reaction and aldol be expanded to better serve as broad concept article-like function, i.e. summary style for the other articles. I presume there is enough content on aldol condensation to warrant a separate article in addition to aldol reaction, so long as they are properly linked and differentiated. All that said, I haven't really scrutinized anything and it will probably take Smokefoot or someone else so inclined to dig into the details and assert some order. My guess is that student editors will mostly try to add content rather than help organize it, and if we have content spread across 4 pages, they will be adding content to 4 pages, making our merge efforts more difficult later on. Mdewman6 (talk) 21:13, 2 October 2023 (UTC)

Unsaturated hydrocarbon article to omit aromatics?

For the article unsaturated hydrocarbon, which is being edited ... My idea, driven by expediency in part, is that the article would not include aromatic hydrocarbons as examples of unsaturated hydrocarbons.

Yes, aromatic compounds can behave as unsaturated compounds, mainly by hydrogenation, but usually the topics are treated separately. If the community is agreeable to this separation, then the introductory paragraph would describe the scope. --Smokefoot (talk) 22:08, 28 September 2023 (UTC)

It seems like better organization is in order across the board- likely involving a merge or merges. We also have:

• Degree of unsaturation
• Unsaturated and saturated compounds
• Unsaturated monomer

in addition to Unsaturated fat and Unsaturated fatty acid, but those are more specific topics obviously. I don't think our readers are served by us presenting the essentially the same concepts in multiple articles with similar titles. That said, if all 4 of the articles above can be better differentiated from each other and properly linked to one another, maybe it's okay. Mdewman6 (talk) 23:18, 28 September 2023 (UTC)

That kind of sleuthing/analysis is very helpful. Multiple similar articles complicates editing/curation. We have also:

• Aromatic compound, which is missing nonbenzenoid aromatics
• Aromaticity mostly about the concept
• Simple aromatic ring, which is almost a gallery, mostly of heteroaromatics
• Hydrocarbon, = C_nH_m (i.e. alkanes, alkenes, alkynes, arenes with no heteroatoms). Article includes a listing/description of many reactions (Substitution, Free-radical substitution, Addition polymerization...), Environmental impact, Origin, i.e. some drift
• Conjugated system (Bonding, Stabilization energy, Generalizations and related concepts, Conjugated cyclic compounds, Aromatic compounds, Nonaromatic and antiaromatic compounds, In pigments, Phthalocyanine compounds, porphyrins and similar compounds, chromophores)
• Alkane, alkene, alkyne, which overlap heavily with unsaturated hydrocarbon. We might agree that these are core topics.

Some preliminary goals:

1. merge unsaturated hydrocarbon and Unsaturated monomer into alkene and alkyne, which are the go-to articles for C=C and C≡C.
2. somehow merge Degree of unsaturation in Unsaturated and saturated compounds, we need an article on unsaturation in chemistry
3. maybe merge Simple aromatic ring into aromatic compound?

If editors do not disagree on the three preliminary ideas, I will start.--Smokefoot (talk) 02:24, 29 September 2023 (UTC)

I generally agree with those 1-3. I did have a thought that unsaturated and saturated compounds is bit unsatisfying as a title per WP:AND. I wonder if something like unsaturation (chemistry) would work? Of course, there would be some ambiguity with the concept of saturation is solutions, but that might be adequately addressed with a hatnote to undersaturation (and saturation#chemistry). I suppose if the merge makes sense, we can worry about the title afterward. Mdewman6 (talk) 23:21, 2 October 2023 (UTC)

Chemistry Libre is gunning for WP

Student homework time, e.g., Wikipedia:Wiki Ed/The University of British Columbia/CHEM 300 (Fall 2023). A major tool for these students is transferring content to Wikipedia from Chemistry Libre (https://chem.libretexts.org), an online textbook. In the same way that Wikipedia is not an RS, it seems that ChemLibre is neither. We want real references.--Smokefoot (talk) 15:20, 5 October 2023 (UTC)

We already have 179 citations to that source. Some of it gives access to standard textbooks. For example, John D. Robert and Marjorie C. Caserio (1977) Basic Principles of Organic Chemistry, second edition is at this link. I'm not sure what we can/should do about this, apart from making the Wiki Ed contact, in this case @User:Ian (Wiki Ed) aware of our general concern that only WP:RS, preferably WP:secondary are used. Mike Turnbull (talk) 15:57, 5 October 2023 (UTC)

I'm unfamiliar with Chemistry Libre. Am I correct in my conclusion that these are OER textbooks which are the work of individual instructors without additional review, and thus more SPS than RS? Ian (Wiki Ed) (talk) 16:43, 5 October 2023 (UTC)

I think it needs careful analysis case-by-case. Some Chemistry Libre is actual formal textbook (McMurry switched his Organic Chemistry, a standard college text, to an OER release there as of its 10th edition). Some are de-novo OER, written as formal textbook (sometimes grant-funded to do so). Some are content-maps and hints to accompany a published textbook (sometimes by the textbook author, sometimes by third-party). Some are more like a professor's lecture notes. Authorship is always given, but refs in the pages themselves are not typically detailed. Some cite wikipedia and/or wikimedia-commons. DMacks (talk) 17:26, 5 October 2023 (UTC)

OK, still trying probing this phenomenon.

https://wiki.riteme.site/w/index.php?title=Organic_synthesis&diff=1179240421&oldid=1179237587is a new example of an editor supporting a claim with ChemLibre. Fair enough. So who wrote the ChemLibre content? The only authorship that one sees is "Synthetic Efficiency is shared under a CC BY-NC-SA 4.0 license and was authored, remixed, and/or curated by LibreTexts." Sounds murky. OK, one can see that this article is part of a larger system "UC Davis Chemistry Chem 231A. Advanced Organic Chemistry. Winter 2017: Prof. Jared Shaw". So, are class notes viewed as reliable sources? Probably not. If it were Roberts and Casserio or MuMurry, couldnt we ask that those specific source be cited or is that too much?

My other complaint is that the act transferring content from ChemLibre to Wikipedia, validates ChemLibre ("see folks, Wikipedia views us as a reliable source") and then ChemLibre becomes elevated in stature. This situation leads to citation spawning.--Smokefoot (talk) 23:42, 8 October 2023 (UTC)

FA review for EBSD

Hi, I wonder if any1 interested can take time and participate in reviewing the Electron backscatter diffraction article and support or oppose my feature article nomination at Wikipedia:Featured article candidates/Electron backscatter diffraction/archive1. Thanks FuzzyMagma (talk) 22:38, 10 October 2023 (UTC)

radius of F- compared to F

I read here Covalent radius of fluorine, that "When F becomes F⁻, it gains one electron but has the same number of protons, meaning the attraction of the protons to the electrons is weaker, and the radius is larger." This is not correct. The electrons are not bunched together. The force between the nucleus and any single electron would be the same unless the radius were made larger for some other reason. The electric force is not shared out among the electrons present. 2603:8080:CE00:6800:A0E1:CC79:C0C3:1801 (talk) 02:13, 1 November 2023 (UTC)

The radius is larger because of the greater repulsion between the electrons. Bduke (talk) 04:50, 1 November 2023 (UTC)

History template help

I recently created the Template:History of physics which has helped to revise and navigate better in between history articles related to physics (and I am working on Draft:Template:History of mathematics). I started a Draft:Template:History of chemistry, however I am not sure I got every history article there is, and some topics could be grouped together as in Template:History of physics. To be precise I am only adding links to articles that are mainly about history (usually titled "History of", "Timeline of", "Chronology of"). I am not adding articles that have a history section like Physical chemistry. Seeing how few articles there are, maybe it is too soon to make this template. Any suggestions? ReyHahn (talk) 13:35, 1 November 2023 (UTC)

Ionic state

I noticed that in Glyphosate#Chemistry, there is the red link Ionic states. What would be the most appropriate article to link to instead? Or should we rather create a new redirect? Leyo 13:09, 9 November 2023 (UTC)

I'd say Ion Jo-Jo Eumerus (talk) 13:38, 9 November 2023 (UTC)

To avoid a WP:SEAOFBLUE, I'd leave it with "ionic states" unlinked. There is already a link to zwitterion which is the most relevant one for glyphosate's state in aqueous solution. Jo-Jo Eumerus is correct that "Ionic state" could be created as a redirect to "Ion" but I'd still leave it out for glyphosate. Mike Turnbull (talk) 14:53, 9 November 2023 (UTC)

Thanks for the responses. I thought Dissociation (chemistry) might also be a possible link target. --Leyo 15:53, 9 November 2023 (UTC)

Cyanimide

I cannot find a coherent topic for this article. Some papers distinguish between cyanimides and cyanamides, while others use it to refer to cyanamides only, or to the parent compound. The sole reference in the article seems to use the term to describe a carbodiimide metal complex, and contrasts with a cyanamide used to synthesize it. The parent carbodiimide is a tautomer of the parent cyanamide. –LaundryPizza03 (dc̄) 09:37, 11 November 2023 (UTC)

I'm not familiar with the term cyanimide. The simplest compound of that type, according to our article cyanimide, would be the dimethyl derivative but Chemspider calls this dimethylcyanamide, which I agree with. Chemspider has no hit for "cyanimide", although that's not definitive. Pubchem gives just one hit for "cyanimide", which is a synonym for N-cyanoformamide. The article cyanimide only cites one source and should be WP:PRODded, IMO. Mike Turnbull (talk) 10:40, 11 November 2023 (UTC)

 Done Otherwise, this will be taken to AfD. –LaundryPizza03 (dc̄) 11:09, 11 November 2023 (UTC)

The ref cited in the cyanimide article does not contain the string "cyanimide". Instead, it is "cyanoimide". I see a few lit-hits for that term. I removed the ref from the article, and I agree that article-deletion is the correct course here (AFD if PROD fails). DMacks (talk) 11:13, 11 November 2023 (UTC)

Cyanimides appears to be >C=N-C≡N or H₂C=N-C≡N. But most references just seem to have it as an error for cyanamide.

Acetamiprid would appear to match that description. --Project Osprey (talk) 22:30, 11 November 2023 (UTC)

@LaundryPizza03 It has been de-prodded by User:Kvng. AfD? Mike Turnbull (talk) 21:40, 17 November 2023 (UTC)

 Done See Wikipedia:Articles for deletion/Cyanimide. –LaundryPizza03 (dc̄) 21:59, 17 November 2023 (UTC)

Good article reassessment for Percy Lavon Julian

Percy Lavon Julian has been nominated for a good article reassessment. If you are interested in the discussion, please participate by adding your comments to the reassessment page. If concerns are not addressed during the review period, the good article status may be removed from the article. Spinixster (chat!) 08:43, 23 November 2023 (UTC)

Weidel's Reaction?

On the page for Hugo Weidel, it mentions that he invented Weidel's reaction. However, there is no article for Weidel's reaction, and I wasn't able to find anything online about the topic. Is anyone in this Wikiproject familiar with it? --MtPenguinMonster (talk) 09:05, 24 November 2023 (UTC)

Seems to be a colorimetric test based on using ammonia to form a murexide. I've found a bunch of old literature that uses it to prove certain chemicals are/aren't present but not an actual ref for the test itself. DMacks (talk) 09:59, 24 November 2023 (UTC)

Perhaps German-language sources say something about it? This book might have one; since it seems to be out of copyright I'll see if one can get a copy. Jo-Jo Eumerus (talk) 10:12, 24 November 2023 (UTC)

The extensive obituary at Zenodo (cited in the article) doesn't seem to mention a test like DMacks found but it does have a complete list of Weidel's publications that may give someone some clues: I don't see anything obvious. Mike Turnbull (talk) 12:17, 24 November 2023 (UTC)

Looks like at least this is now public. Jo-Jo Eumerus (talk) 07:57, 28 November 2023 (UTC)

Looks like it's use of halogen-water followed by ammonia, distinguished from the murexide test that instead uses nitric acid, based on:

• Rieder, Hermann (1899). Atlas of Urinary Sediments: With Special Reference to Their Clinical Significance. p. 45.

which cites

• F. Gowland Hophins, in Schäfer's "Physiology"

Here is a procedure for these two related tests:

"(d) Xanthine test.—Dissolve the residue or half of it in nitric acid and evaporate cautiously to dryness on a crucible cover over a small flame. A lemon-yellow residue results, which becomes intensely red on moistening with caustic soda, and on further heating purplishred. Add a few drops of water and warm; a yellow solution results, which again gives a red residue on evaporation (distinction from the murexide reaction for uric acid).

"(e) The so-called Weidel's reaction.—Dissolve half of the xanthine obtained in bromine water, warming gently, evaporate the solution on the water-bath to dryness, and invert the dish over another which contains some ammonia. The residue becomes red."

from

• Bevier, Isabel; Usher, Susannah (1908). Food and Nutrition Laboratory Manual, Department of Household Science, University of Illinois (PDF). pp. 55–56.

and that ref cites "Salkowski" (don't have time to track that one deeper). DMacks (talk) 05:18, 26 November 2023 (UTC)

Foul-smelling chemicals

This category has been nominated for deletion. Any comments here Wikipedia:Categories_for_discussion/Log/2023_November_29#Category:Foul-smelling_chemicals Meodipt (talk) 09:17, 6 December 2023 (UTC)

UBC is nearing semester's end

In a few days, editors might take a look at the many articles being revised by students at UBC. A lot of their work seems unsupervised, and it appears that the instructors evaluate these assignment based on number of words (vs quality). Some content seems to cross the line with regards to WP:NOTTEXTBOOK at least. It looks like they are winding down for the semester. A good place to start is organic synthesis. Is organic synthesis really about reflux condensers or is it about, well, synthesis? --Smokefoot (talk) 03:37, 6 December 2023 (UTC)

The version at the end of June this year was dreadful. The current version is still poor but an improvement. Personally, I wouldn't attempt to cover such a large topic in a single article but I guess we shouldn't stop others from trying. Mike Turnbull (talk) 11:33, 6 December 2023 (UTC)

Additions requested to X-ray crystallography and Crystallography

I have done some work on both of these, mainly removing fluff from X-ray crystallography and some cleaning of Crystallography. Both need significantly more work, and there are topic (e.g. macromolecular crystallography) where I don't know enough. I would appreciate the addition of sources and useful edits on the pages; comments OK but useful edits are better. Ldm1954 (talk) 17:37, 6 December 2023 (UTC)

Good article reassessment for Liquid crystal

Liquid crystal has been nominated for a good article reassessment. If you are interested in the discussion, please participate by adding your comments to the reassessment page. If concerns are not addressed during the review period, the good article status may be removed from the article. ~~ AirshipJungleman29 (talk) 20:22, 8 December 2023 (UTC)

Comparison of chemistry and physics

Does Comparison of chemistry and physics work as an article? It reads more like an essay to me. XOR'easter (talk) 03:07, 16 November 2023 (UTC)

+1. It's surprising to see that the article exists for twelve years already. --Leyo 20:26, 17 November 2023 (UTC)

I noticed that the article was moved to Relationship between chemistry and physics. Do we need to keep the old name as a redirect? --Leyo 08:51, 11 December 2023 (UTC)

Undeclared AI content

The newly added article CHNOPS appears to me to be mostly or entirely generated by an AI chatbot, based on it's consistently flat tone, impeccable grammar and organization, bizarre mixture of vague generalities with potent and tightly worded sentences, odd lapses of logic, and sophisticated associations and vocabulary not characteristic of a student editor. I can't find it lifted from the web but can generate eerily similar article sections by prompting ChatGPT 4.0 to write them simply by asking for an emphasis on astrochemistry. I had intended to simply improve it without prejudice about its source, but found it intensely frustrating and disorienting to try to verify the claims with the cited sources, so I am done trying. I would just delete it but don't want jump the gun if there is a better process that would document it and help prevent more of it. Do others agree that it is probable undeclared AI content, and what is an appropriate course of action? –MadeOfAtoms (talk) 07:42, 11 December 2023 (UTC)

I have looked a quite a few that would be from the same class. CHON also describes some of the same and has a redirect: CHONPS. I will take a closer look at what I reviewed in the last days and comment. Graeme Bartlett (talk) 08:37, 11 December 2023 (UTC)

Other things from the same class ( University_of_Washington/ASTBIO_502_Astrobiology_Special_Topics_-Origin_Of_Life_(Autumn_2023)): Cyanosulfidic prebiotic synthesis, The Polyelectrolyte Theory of the Gene, Proto-metabolism, Warm little pond, Stellar influences on an origin of life setting.. Graeme Bartlett (talk) 09:32, 11 December 2023 (UTC)

List of all article edited: https://dashboard.wikiedu.org/courses/University_of_Washington/ASTBIO_502_Astrobiology_Special_Topics_-Origin_Of_Life_(Autumn_2023)/articles/edited? Graeme Bartlett (talk) 09:35, 11 December 2023 (UTC)

Thank you Graeme Bartlett. There is also discussion of recent edits to CHON and CHNOPS at User talk:Drmies#Something_wrong_here?. –MadeOfAtoms (talk) 00:44, 13 December 2023 (UTC)

Introduction to the heaviest elements

I started a conversation about Introduction to the heaviest elements and its relevance at WT:Physics. It does not seem like a proper introductory topic article. However it seems to serve as a filler for many articles (transclusion) of heavy elements (e.g. bohrium). What is the policiy on this? ReyHahn (talk) 09:25, 17 November 2023 (UTC)

@ReyHahn: reads like an essay. Wikipedia is not a forum for free-form essay writing More to my point: Wikipedia presents knowledge, we do not aim to write textbooks or our personal views on a field. All editors are always writing "introduction to ..." That basically is all we do, introduce. My advice, merge uniquely fact-based aspects of your essay into Heavy elements. Otherwise, do you really want all editors to write "introduction to [your field here]? --Smokefoot (talk) 15:30, 17 November 2023 (UTC)

@Smokefoot It wasn't ReyHahn's creation but mainly that of User:R8R. The policy is WP:NOTESSAY but I have no opinion on that particular article. Mike Turnbull (talk) 16:55, 17 November 2023 (UTC)

@Smokefoot: Sorry if I did not explain myself correctly it is not my essay it's been there for a while. The question is what to do with it?--ReyHahn (talk) 17:02, 17 November 2023 (UTC)

merge it with something else. --Smokefoot (talk) 17:28, 17 November 2023 (UTC)

But merge it where? It is transcluded in 20 elements articles.--ReyHahn (talk) 19:37, 17 November 2023 (UTC)

All these articles have gone through good article review, so I'm sure this will have been discussed before. However, the two featured articles, plutonium and californium don't include the excerpt. The normal place for this sort of issue to be discussed by chemists is at WT:WikiProject Elements and I'm sure our active editors such as User:Double sharp will want to comment. Mike Turnbull (talk) 20:22, 17 November 2023 (UTC)

This was discussed here, back when R8R and I were bringing hassium (108) to FA. The reason Pu (94) and Cf (98) don't have it is that it's only relevant for element 102 (nobelium) onward, where the only way to produce them is heavy-ion bombardment – including the featured articles dubnium (105), hassium (108), nihonium (113), tennessine (117), and oganesson (118). (Lighter transuranics are simply produced by neutron or alpha-particle irradiation and don't face as much difficulty.) The reason why this is transcluded everywhere is because these elements don't exist in nature and have to be produced in this rather niche way, that we can't reasonably expect the average reader to know; on the other hand, a summary would be pretty much the same for everything from 102 onward. Repeatedly transcluding the same text seemed a reasonable way forward in this case (I am pretty sure there must be other examples in WP, but can't think of them at the moment). Double sharp (talk) 00:50, 18 November 2023 (UTC)

I posted this question at WT:PHY before posting it here. Their suggestion seems reasonable, to merge Introduction to the heaviest elements into Superheavy elements#Introduction and transclude that section.--ReyHahn (talk) 12:23, 20 November 2023 (UTC)

 Done--ReyHahn (talk) 15:07, 19 December 2023 (UTC)

Quantum Computational Chemistry Page Permission

Hi there,

Sorry to bother you but I was wondering if I could create a new page called Quantum Computational Chemistry within this Wikiproject.This would entail moving the section titled "Quantum Computational Chemistry" in Computational Chemistry to it's own page then adding a subsection to Methods called Quantum Computational Chemistry. I would then proceed to create a brief abstract about quantum computational chemistry in the methods sections.

Please find the page moved in draft mode:

https://wiki.riteme.site/wiki/User:Erdabravest/Quantum_Computational_Chemistry — Preceding unsigned comment added by Erdabravest (talk • contribs) 10:27, 19 December 2023 (UTC)

Regards Erdabravest2001 (talk) 08:03, 19 December 2023 (UTC)

Sounds OK, but it should be titled Quantum computational chemistry Graeme Bartlett (talk) 11:09, 19 December 2023 (UTC)

The article (a better word than the wider concept of "page") computational chemistry already contains the word "quantum" 34 times in its body text and uses the template {{main}} in several places to link to more specialist sub-articles. You will need to be careful that you are not duplicating these. On the other hand, your draft looks to be very well referenced and up-to-date. If I were you I'd be somewhat WP:CAUTIOUS: the current article has 171 page watchers and many won't be members of this WikiProject. I see that you are currently in a discussion on its Talk Page about a GA review and I think that you should use that to get feedback on the final structure of the linked articles. Mike Turnbull (talk) 11:22, 19 December 2023 (UTC)

.... P.S. No-one requires permission to write articles: Wikipedia's core principle "be bold" is part of the reason for its success. Mike Turnbull (talk) 11:26, 19 December 2023 (UTC)

In parallel with the above encouragement, some guidelines to bear in mind:

• WP:TERTIARY: an article on a really important topic will cite modern comprehensive textbooks, the bibles of the field.
• WP:NOTTEXTBOOK, even though Wikipedia is an educational tool, the aim is to present facts, not explain them.
• dont cite yourself or your pals, WP:COI, sorta obvious/ridiculous, but many new contributors engage in self-citation, etc.--Smokefoot (talk) 14:08, 19 December 2023 (UTC)

What is the relationship between the User:Erdabravest2001 and User:Erdabravest accounts? DMacks (talk) 15:24, 19 December 2023 (UTC)

I believe that User:Erdabravest2001 is a school-associated account and User:Erdabravest is intended to be separate, according to a reply on Talk:Computational_chemistry/GA2. Reconrabbit (talk|edits) 15:27, 19 December 2023 (UTC)

Got it. Thanks for finding that. No behavioral concerns to my eye either, just was getting confused at first glance. DMacks (talk) 15:30, 19 December 2023 (UTC)

Hi there,

Yeah, exactly. The difference between Erdabravest2001 and Erdabravest is that Erdabravest2001 was created as part of WikiEdu. Erdabravest was created to ensure I could continue contributing to Wikipedia. Erdabravest (talk) 18:23, 19 December 2023 (UTC)

Requested move at Talk:Timeline of chemical element discoveries#Requested move 10 January 2024

There is a requested move discussion at Talk:Timeline of chemical element discoveries#Requested move 10 January 2024 that may be of interest to members of this WikiProject. Remsense留 21:19, 10 January 2024 (UTC)

Discussion at 1,1'-Bis(diphenylphosphino)ferrocene

 You are invited to join the discussion at Talk:1,1'-Bis(diphenylphosphino)ferrocene#Requested move 4 January 2024, which is within the scope of this WikiProject. DMacks (talk) 19:53, 4 January 2024 (UTC)

Unfortunately, the outcome was not moved, i.e., en.wikipedia (as opposed to de.wikipedia) will not strive towards typographical accuracy and will remain messy in this sense. --Leyo 14:48, 11 January 2024 (UTC)

Salt vs ionic compound vs alkali salt

As described emphatically at Talk:Salt (chemistry), Salt vs ionic compound vs alkali salt needs to be revisited and maybe merged. Page views per day are 750, 260, 44, respectively. Hefty. I can tag them for merge, but to what? My slight preference is Talk:Salt (chemistry) because its more common language. --Smokefoot (talk) 14:23, 19 January 2024 (UTC)

I would support that. We don't always follow IUPAC, but the goldbook acknowledges salt but not ionic compound (it goes for ionic bond instead). --Project Osprey (talk) 14:56, 19 January 2024 (UTC)

I am directing the merge discussion to here since these articles seem particularly impactful. If someone doesnt like that plan, I will modify the link. --Smokefoot (talk) 16:21, 19 January 2024 (UTC)

Support merge/redirect of ionic compound into salt (chemistry). I was prepared to support the opposite direction or oppose it at all (see my later-struck commentas my original struck comment at the previous discussion), because the lay definition of "salt" that is often taught is strictly as an acid–base neutralization product, but obviously salts can be made in other ways and the notional "acid" and "base" don't always make sense (H₂ as the acid to form NaH salt; what the hell is the base that is neutralized to form NaOH?). But "ionic compound" is confusing because an "ion" could well be a covalent cluster so the classifications become confusing. "Ammonium nitrate is a salt; the atoms within each ion are connected by covalent bonds, with an ionic bond between the ions" is a clean statement whereas "ammonium nitrate is an ionic compound" is true but it leads to the false conclusion "it's ionic therefore therefore it does not contain covalent bonds". Therefore I go with IUPAC because they're the experts and I don't see any clear reason to do otherwise. And it avoids the problem of thinking a zwitterion dissociates in water: it clearly has ionic character, but it is not , given it is "ionic" (but does not contain ionic bDMacks (talk) 16:31, 19 January 2024 (UTC)

Defer alkali salt until we establish the scope of 'salt'. But once so, we should also include acid salt in the discussion. DMacks (talk) 16:31, 19 January 2024 (UTC)

Comment 6.5 years ago, we had Talk:Salt (chemistry)#Merger proposal where User:OrganoMetallurgy and I agreed with "merge salt + ionic compound" (and nobody else commented), but it never happened and there was no mention of a preferred direction for the merger. DMacks (talk) 16:41, 19 January 2024 (UTC)

Well, since this merge was previously discussed without objection (or much of any comment), I made a draft at User:Smokefoot/sandbox#Mergerino. I blended the lede, but cut and pasted the rest of the sections. The components of each section from salt (chemistry) follows the section from ionic compound, signalled by some initial red characters. So, if anyone has a desire to tweak what I made, go for it, otherwise in a few days, I will paste my version into salt (chemistry) and anneal it, then you can take a whack.--Smokefoot (talk) 02:44, 20 January 2024 (UTC)

Your mergerino is looking good. I'll take a closer look when I have time. It would be a good idea to re-do the GA assessment which ionic compound had in 2017 once you have finished. My preference for the merger is to salt (chemistry), mainly for the reason that many organic compounds have both ionic and covalent bonds and the term "salt" is fine for these. Mike Turnbull (talk) 16:32, 20 January 2024 (UTC)

Huge 'thank you' to Smokefoot for doing the heavy lifting on this! DMacks (talk) 18:06, 21 January 2024 (UTC)

Category:Name organic reactions has been nominated for renaming

Category:Name organic reactions, which is within the scope of this WikiProject, has been nominated for renaming. A discussion is taking place to decide whether it complies with the categorization guidelines. If you would like to participate in the discussion, you are invited to add your comments at the category's entry on the categories for discussion page. Thank you. DMacks (talk) 21:59, 21 January 2024 (UTC)

Our editors

Somehow, I've only just become aware of this Bot, which keeps track of editors on any given wikiproject:

• Wikipedia:WikiProject_Directory/Description/WikiProject_Chemistry
• Wikipedia:WikiProject_Directory/Description/WikiProject_Chemicals

Between about 120-130 editors edited 5 or more pages associated with WP:Chem or WP:chemicals in the last 30 days. Looking at the lists I can see everyone I would expect to see, plus highly active WikiGnomes and some spill over from adjacent WikiProjects - but about two-thirds to three-quarters I don't recognise. Obviously there will be false positives, but I thought the list might be useful to identify orphan editors or trouble makers. Project Osprey (talk) 21:17, 27 January 2024 (UTC)

I don't think it will be that useful to us, since Wikipedia:WikiProject Directory has been inactive for quite some time, and User:Reports bot has not been updating any of the pages since 2022.

There is something I would like to bring up related to this though: is it possible for this Wikiproject to get updates on new discussions? I use the page that Reports bot generates on WP OSH and it's pretty neat. Reconrabbit 21:28, 27 January 2024 (UTC)

I hadn't noticed that... blast! I wonder if that function is now performed by other bots? I had a look at ToolForge but I couldn't see anything similar. The talk page aggregation you're talking about also seems to be handled by Reports_bot (a part of it which is still working). It doesn't currently cover this project, I guess we would have to ask User:Harej? --Project Osprey (talk) 00:13, 28 January 2024 (UTC)

Good article reassessment for Continuous distillation

Continuous distillation has been nominated for a good article reassessment. If you are interested in the discussion, please participate by adding your comments to the reassessment page. If concerns are not addressed during the review period, the good article status may be removed from the article. ~~ AirshipJungleman29 (talk) 04:04, 31 January 2024 (UTC)

Wikipedia:WikiProject Chemistry

I might be wrong, but my feeling is that Wikipedia:WikiProject Chemistry (project page) was getting old and dusty. So I removed almost all of the to-do list (most had been done), and rewrote some global statements. Others are encouraged to revise or revert or overwrite what is there. Goals of this page might be to welcome, guide, and, maybe, boast a little. --Smokefoot (talk) 16:42, 27 January 2024 (UTC)

We need to add to the to-do list as it is looking pretty sparse! Graeme Bartlett (talk) 09:55, 31 January 2024 (UTC)

The "things you can do" frame? I can add some more articles as I find them in the cleanup listing. Just added Glucoside, as it's still largely based on a 1911 source. Reconrabbit 12:28, 31 January 2024 (UTC)

Requested move at Talk:Polymorphism (materials science)#Requested move 13 January 2024

There is a requested move discussion at Talk:Polymorphism (materials science)#Requested move 13 January 2024 that may be of interest to members of this WikiProject. – robertsky (talk) 12:37, 5 February 2024 (UTC)

Chemists in the Spotlight: Portraying Joseph W. Kennedy in 'Oppenheimer'

I'm working on the Wikipedia article for Draft:Troy Bronson 2024, particularly his role in "Oppenheimer" where he portrays Joseph W. Kennedy, a chemistry key figure in the discovery of plutonium. This part of the article touches on significant scientific achievements and the portrayal of chemists in popular media.

I thought it might be interesting and beneficial to bring this to the attention of experts here. I'm curious about your thoughts on how chemists and their work are represented in films and media, especially in historical contexts like the Manhattan Project. Are there aspects or nuances about the portrayal of chemists and their discoveries that you think are often overlooked or misrepresented?

Your insights could help ensure the article not only highlights Bronson's role but also respects the scientific integrity and contributions of the real-life figures it depicts. Plus, it could be a fun way to bridge the gap between chemistry and popular culture in our content.

Looking forward to any thoughts or comments you might have!

EagleSleuth~~~~ EagleSleuth (talk) 05:02, 7 February 2024 (UTC)

I think most people would be able to name a famous physicist (Hawking, Marie Curie, Newton) and maybe a biologist (Darwin?) but not a famous chemist. We're usually relegated to the status of 'scientists' in the media. We seem to be different than the other major branches of science. Physics and biology discover cool and useful facts, but chemists just make nasty stuff which people get angry about (plastics, pesticides, PFAS, vaccines etc). Our public image isn't great. --Project Osprey (talk) 10:41, 7 February 2024 (UTC)

The unsurmountable temptation to copy - an indicator of high quality?

There seems to be a shift in the opinions regarding the quality of Wikipedia articles. Some of us veterans may still remember the times when referring to our articles was faced with scoffs and ridicule. Few years ago I spotted a book published by Elsevier that had utilized Wikipedia content to the extent it was then withdrawn. Now I found another, Heterocyclic Chemistry by Alvin Pugh published by Edtech Press. If one compares the entries of this book to the corresponding Wikipedia articles they might find surprising amount of similarities. The optimist in me sees this as a sign of high quality in our end and not as just the laziness and greed of authors and predatory publishers. Any other views? Nitraus (talk) 12:22, 7 February 2024 (UTC)

Cynically, the Internet has conditioned people to expect information without having to pay for it, so folks now can't get money for proper writing/journalism and need to plagiarize instead. Jo-Jo Eumerus (talk) 15:32, 7 February 2024 (UTC)

Two semi-random samples. IDENTICAL wording in this book and Wikipedia.

Atrane: "Silatranes exhibit unusual properties as well as biological activity in which the coordination of nitrogen to silane plays an important role. Some derivatives such as phenylsilatrane are highly toxic." Identical." Benzbromarone: "Benzbromarone is a uricosuric agent and non-competitive inhibitor of xanthine oxidase[1] used in the treatment of gout, especially when allopurinol, a first-line treatment, fails or produces intolerable adverse effects." --Smokefoot (talk) 14:04, 7 February 2024 (UTC)

"We're awesome, as demonstrated by other people's violating our license policy!" Last year, User:Smartse identified plagiarism from WP in two other Edtech Press titles.[1]. Nitraus or Smokefoot, please update WP:PUS when you find this situation. DMacks (talk) 14:43, 7 February 2024 (UTC)

Bicapped square antiprism

Hello. I am not an expert in chemistry, but I have an article related to this topic. In this source, the bicapped square antiprism may have an example of such cluster, that is ${\ce {Ni_{10}C(CO)_{18}^{2-}}}$. But I do not know whether this is correct (from the article I linked). I really appreciate someone explaining the technical of this chemistry topic. Thank you. Dedhert.Jr (talk) 14:24, 12 February 2024 (UTC)

@Dedhert.Jr The sources do seem to support the text in our article. The links (to Google books) give the specific pages with the information. I don't like the section title "Application" in the article: I would rather call this "Occurrences" or "Examples". You should be able to get a better feeling of the geometry of the antiprism by clicking on the 3D model image: this opens to a larger version which can be moved around to get a comparison with the diagrams in the publications. I presume that the chemical details were confirmed by X-ray crystallography. Mike Turnbull (talk) 14:55, 12 February 2024 (UTC)

For such "deltahedra", the boron hydrides are always a good source. Check out the closo clusters [B₁₀H₁₀]^2-, [CB₉H₁₀]^-, [C₂B₈H₁₀], [NB₉H₁₀]. There may be some zintl ions with that geometry.--Smokefoot (talk) 15:41, 12 February 2024 (UTC)

doi:10.1021/ic00099a031 supports this geometry for [C₂B₈H₁₀] using electron diffraction. DMacks (talk) 16:00, 12 February 2024 (UTC)

Another example: File:Decaborate(10)-dianion-from-xtal-3D-bs-17.png. Ben (talk) 23:40, 12 February 2024 (UTC)

@Michael D. Turnbull. Thank you for suggestions. But I think that applications is more suitable in the context, and we have two GA articles Square pyramid and Triaugmented triangular prism in which the geometry of chemical compounds explicitly described in the applications. I do think there are some other applications of gyroelongated square bipyramid, and the section of that article may have some connection with a project.

As well as explanation of the article I linked, is it possible to create a new article Bicapped square antiprism molecular geometry, along with the sources provision? Dedhert.Jr (talk) 01:45, 13 February 2024 (UTC)

I the ideal world, we would edit square antiprismatic molecular geometry, with a subsection on the capping processes. In that way, we could also acknowledge the mono-capped shape corresponding to the nido clusters related to B9H13.--Smokefoot (talk) 02:39, 13 February 2024 (UTC)

I'm no expert in chemistry once again, and maybe for the better idea, creating a section that contains a similar chemical compound: square prismatic and cubic geometry, capped and bicapped square antiprismatic molecular geometry? But perhaps we already have capped square antiprismatic molecular geometry, and the bicapped one could fit inside as well? That's my opinion; any other ideas are welcome. Dedhert.Jr (talk) 11:19, 13 February 2024 (UTC)

Someone needs to check the symmetry groups: C4v and D4h for mono- and bicapped? --Smokefoot (talk) 14:03, 13 February 2024 (UTC)

The point groups look fine to me, assuming that the substituents are all the same excluding the center. Bicapped square antiprismatic might just be d4 though depending on the identity of the different species, but that might leave you with a different geometry altogether. (Update: Just confirmed that it should be D4d. D4h is the group for a bicapped cube.) Reconrabbit 00:15, 14 February 2024 (UTC)

Speaking of which, in the article Polyhedral skeletal electron pair theory, what does 4n rules means here? Does it refer to the triangular face polyhedron? I'm kind of planning to add them to the article I linked, but it is not very clear to describe such rules, and it is somewhat technical to comprehend. Dedhert.Jr (talk) 04:13, 14 February 2024 (UTC)

n refers to the number of electrons provided by a vertex. I'm a little rusty on it, but HB "counts" as a 2-electron vertex. B has three valence electrons (third column) but allocates one electron to forming a very strong B-H bond (H provides the other). The remaining 2e are then available as the glue to hold the polyhedron together. The main parameters are number of "cluster electrons" and the number of vertices (B, C, metal atoms). There are magic numbers, which give deltahedra. Its a big area. Things get complicated because, for example, Fe(CO)₃ also is viewed as a 2-electron vertex. --Smokefoot (talk) 23:38, 14 February 2024 (UTC)

Functional group compatibility

It appears that we lack an article on functional group compatibility. If anyone wants to create it, the new article or new section would be immediately linkable to multiple pre-existing articles, which is always very satisfying. One thought is that it could be a section within Protecting group or within functional group. March's organic text refers to the term 5x within the context of specific reactions. --Smokefoot (talk) 23:38, 14 February 2024 (UTC)

How to write crystal water in the chem template

For Tahoka Formation, how do I write the dot between the water and the rest of the formula? Jo-Jo Eumerus (talk) 09:51, 28 February 2024 (UTC)

Don't use chem, it has ugly output, instead use chem2. Chem2 converted the * to a centre-dot · . However I prefer to use • as it is more visible. Graeme Bartlett (talk) 10:51, 28 February 2024 (UTC)

Split x-ray diffraction from x-ray crystallography

I propose splitting X-ray diffraction out of X-ray crystallography, discussion started at Talk:X-ray crystallography#Split x-ray diffraction and crystallography. The two are not the same, and there are many areas of XRD where the focus is not on detailed determination of atomic positions. Examples are powder diffraction where comparison is made to known samples, SAXS and many more. There are many areas/pages where it is relevant to say "use XRD" but wrong to say use "X-ray crystallography This would also help to improve the current rambling X-ray crystallography page. Comments to the X-ray crystallography talk page please. Ldm1954 (talk) 08:40, 14 April 2024 (UTC)

Definitions of chemical element

Is there a reason the definition of chemical element seems to vary according to the date you look at the article ? Currently it is defined as a monotypical atomic substance, but a few years ago it was the "species of atom with same atomic number" that was used. I wonder why it's not even mentioned in the article now, the Goldbook cited in the introduction gives the two. frwiki, dewiki, itwiki uses the atomic one, if I'm not mistaken.

The first one seems more complicated and actually a bit dated/historical, the second one is more convenient. The first one is « simple substance  » on Wikidata and there are several wikis that have articles about that. Maybe we should sort the interwikis and move articles to the right item ? TomT0m (talk) 19:26, 22 April 2024 (UTC)

Class of DNA/RNA monomer-related structures

Nucleobase is the heterocyclic variable group, nucleoside is nucleobase+sugar, nucleotide is nucleotide+phosphate. Is there a term for the parent category containing all of those? I'm working on organizing some synthetic-biology chemical pages, for which we don't have very many of any one of those three but we have some and they do form a coherent topic set. DMacks (talk) 16:39, 1 May 2024 (UTC)

Seems like a very worthy project. It looks like we have a full complement of articles on the main natural nucleosides, although some articles might lack a basic ref to a standard biochem textbook. Is there a good online biochem textbook that is not behind a paywall? It would be appropriate to have articles for each of the main natural nucleotide monophosphates (and eventually all of the diphosphates and triphosphates). I am trying to think of what core info we might want for these articles because otherwise their physical properties are probably comparable and unremarkable. Maybe their tautomers (for the nucleobase articles), base-pairing partners, their susceptibility to modification (N- or O-methylation as in epigenetics). Good luck. --Smokefoot (talk) 16:18, 2 May 2024 (UTC)

Coverage of chemistry competitions for school pupils

I am asking for the support of this community to move the following page from drafts to articles: https://wiki.riteme.site/wiki/Draft_talk:Baltic_Chemistry_Olympiad. That will help with increasing the coverage of chemistry competitions.

Wikipedia covers several major competitions, such as the International Chemistry Olympiad and USNCO. However, there should be more pages to raise awareness. I have written a detailed overview of the Baltic Chemistry Olympiad and Competitions. It is one of the oldest international competitions, which over 30 years generated over 180 problems for training students and popularising chemistry.

Olunet (talk) 10:04, 11 May 2024 (UTC)

Wikipedia:Articles for deletion/Baltic Chemistry Olympiad was why it was deleted. Graeme Bartlett (talk) 10:30, 11 May 2024 (UTC)

Migratory insertion

Hi all, I am a new user I was refining Draft:Fausto Calderazzo and I have moved some of the content in the article Migratory insertion. I have also enlarged the article Insertion reaction. Could you please provide some feedback? Thank you in advance.--Diegoriccio98 (talk) 13:14, 17 May 2024 (UTC)

It is valuable to mention the old work on RMn(CO)5 but not much more. Wiki articles rarely describe how experiments were conducted. And we do not explain very much (WP:NOTTEXTBOOK), Instead our articles focus on facts, the results of experiments, not how they are designed (we want the "baby, not the delivery"). You may consider writing an article about MeMn(CO)5 or its acetyl derivative if you feel the urge to present the details for that work. Migratory insertion is an important step in several catalytic cycles (zero involve Mn), so we want the article to remain general. And a lot of work has been done since the 1960's, some summarized in Hartwig's textbook.--Smokefoot (talk) 14:59, 17 May 2024 (UTC)

The expression "feel the urge" is unkind. I am a student who was studying the history of chemistry in his free time, I found this platform quite "rude" so far despite my goodwill and some recent development add more complication. Some replies I have received so far are too generic to be useful (not yours), so I think I should stop it here. Thank you all and see you maybe in the future.--Diegoriccio98 (talk) 15:58, 17 May 2024 (UTC)

Chiral phosphates

Would I be correct in my belief that the phosphate groups in DNA and RNA are chiral at P? Project Osprey (talk) 19:44, 26 May 2024 (UTC)

The phosphate substructures would not be chiral. Line bond drawings for the DNA backbone are drawn asymmetrically, with one of these oxygen atoms as part of a P=O double bond, but bond resonance renders the substructure to be symmetrical. I'm sure there are a multitude of ways that the symmetry can be broken. One off the top of my head would be if one of the oxygen atoms, not part of a phosphodiester bond, is a rarer isotope, O¹⁷ or O¹⁸. ― Synpath 00:00, 27 May 2024 (UTC)

Always fun to jump onto such arcane questions with imperfect knowledge: My understanding is that since DNA/RNA are chiral so the two terminal P-O's are nonequivalent. Every O is nonequivalent. Its asymmetric (not just dissymmetric). This comment is related to the problematic concept of "chiral center" and all that. IMHO. Now about chiral phosphates, that topic was a "thing" several decades ago with the prep of ROP¹⁶O¹⁷O¹⁸O^2- by Knowles at Harvard (https://www.annualreviews.org/content/journals/10.1146/annurev.bi.49.070180.004305). There is another P-chiral Knowles, who got a Nobel for chiral phosphines. --Smokefoot (talk) 00:23, 27 May 2024 (UTC)

Yes, a bit of sloppy language on my part. I meant the phosphate P atoms in typical DNA/RNA polymer are not stereogenic centres. Side note, I was left in a bit of awe when I first learned that you can actually synthesize chiral phosphates reliably to query enzymatic reaction mechanisms. Though, I only recall a MeOP¹⁶O¹⁸OS^2- system. ― Synpath 00:51, 27 May 2024 (UTC)

Chemical structure of DNA; hydrogen bonds shown as dotted lines.

Thank you both. I've added a picture to try and help explain myself. The organophosphate groups here consist of a P bonded to 4 different groups, arraigned in rough tetrahedron O=P(O^-)(OR¹)(OR²). If that P was a C it would undoubtedly be chiral (obviously allowing for the =O being some other comparable group that satisfies the bond order). Synpath raises the issue of resonance but that isn't really a description of the ground state, I think at most that would allow the molecule to convert between 2 or more forms, all of which would be chiral. I'm also not sure how much phosphate is able to engage in resonance anyway, the bonding around P is exceedingly complex and I barely understand it - but to my mind the process of resonance shares themes with SN2 attack (no change in overall bond number, even at the transition state). Hydrolysis reactions are incredibly slow in phosphates, the uncatalyzed hydrolysis of dimethyl phosphate proceeds at about 1 × 10⁻¹⁵ s⁻¹ that's a half life of thousands of years.

Maybe others can explain better. I recommend omitting resonance, a bonding concept that just blurs the picture. All atoms in an asymmetric entity are nonequivalent (diastereotopic). Nonequivalence is usually the key question, i.e. every atom and every single bond reacts at a distinct rate (except for coincidences), and every single atom shows a separate NMR resonance. In DNA/RNA the chirality originates in the sugar residue, which dictates the spirality of the helix. If that pentose could be inverted, the helix will reverse.--Smokefoot (talk) 14:04, 27 May 2024 (UTC)

Wrt your statement: [resonance] would allow the molecule to convert between 2 or more forms, all of which would be chiral. there is technically no interconversion between forms in resonance. The discreet resonance contributors we draw are just the extremes the molecule could take on, and the reality is closer to the weighted average of these contributors. That's why if you have a 50/50 mix of two resonance contributors of opposite chirality the actual molecule is achiral.

Phosphates do have more complicated bonding patterns but can be thought of as undergoing bond resonance in a similar manner to lighter organic elements, even if it is not an accurate picture of the electronic structure of the molecule. Bond resonance is just an abstract tool for reasoning on molecular chemistry without having to go do quantum calculations, and it works here well enough. Bond length changes for phosphate and variously substituted phosphates are consistent with typical resonance reasoning. For example, the bond lengths to both unsubstituted phosphate oxygen atoms in DNA are ~1.485 Å, while those in PO3−4 are ~1.578 Å (numbers pulled from Protein Data Bank, PDB ID: 3BEP and PDB ID: PO4). ― Synpath 18:56, 27 May 2024 (UTC)

Renaming the "Monolayer-protected cluster molecules" page

I originally asked about this topic here in Helpdesk. It was suggested that before applying for the move of the article, there should be some discussion about how to name it.

The "Monolayer-protected cluster molecules" page is focused on the crystal structures of these nanoclusters in a list-like manner. The current tittle was generated when the page was accepted but it seems too general or ambiguous. There already exists pages like Nanocluster and Thiolate-protected gold cluster, tittles of which feel very similar, even if the contents serve a different purpose. I would call the page as "Crystallized monolayer-protected clusters" or "List of crystallized monolayer-protected clusters". In the text it was stated that "This article is designed to be a list of known structures of MPCs", therefore the new tittle would reflect more clearly the contents than the current one. What do you suggest? Iridium27 (talk) 09:28, 30 May 2024 (UTC)

The reason I used a name like that, is that I think that a more general title is better than a narrower title. Thiolate-protected gold cluster would be a narrower topic. Nanocluster does not imply that there is one layer of ligands, or that it occurs in isolation (could be ions, or as a 3D solid), So I think this article is sufficiently different from those. Currently it is just a list, but it would be fair enough to have more introduction on why they are important, and general facts about them. Graeme Bartlett (talk) 04:46, 1 June 2024 (UTC)