User talk:Smokefoot

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References

^ . doi:10.1039/jr9560001312. {{cite journal}}: Cite journal requires |journal= (help); Missing or empty |title= (help)

CS1 error on 1-Pentyne

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CS1 error on Methyl group

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CS1 error on Hydrogen bond

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CS1 error on Phosphoric acid

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CS1 error on Starch

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CS1 error on Lanthanum acetylacetonate

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CS1 error on Europium acetylacetonate

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CS1 error on Gadolinium acetylacetonate

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CS1 error on Samarium(III) acetylacetonate

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CS1 error on Samarium(III) acetylacetonate

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CS1 error on Thulium acetylacetonate

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CS1 error on Terbium acetylacetonate

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List of colleges and universities in the United States by endowment

The last edit states, "New York is one of the few populous states without a public university with a large endowment." The statement is only correct in the context of the NACUBO list, and it ignores State University of New York as written.

While the statement on smaller populations is true, my minor concern is the subtle implication of a conclusion not stated by a cited source. With that said, the entire paragraph could probably benefit from another citation or two. Redraiderengineer (talk) 18:02, 6 February 2024 (UTC) @Redraiderengineer:I was intrigued by the earlier request for a RS, but it seems that the information provided by my addition is common knowledge, WP:CK. So what would one cite, a source for the populations of these states? As for New York state having few well-endowed public universities, that info is provided by NACUBO, and their data are reproduced in the table. Let me know what you think. --Smokefoot (talk) 18:25, 6 February 2024 (UTC)[reply]

CS1 error on Triphenylbismuth

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CS1 error on Naphthenic acid

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CS1 error on Urushibara nickel

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CS1 error on Isopropylmagnesium chloride

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CS1 error on Ethylene

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Invitation to join New pages patrol

Hello Smokefoot!

The New Pages Patrol is currently struggling to keep up with the influx of new articles needing review. We could use a few extra hands to help.
We think that someone with your activity and experience is very likely to meet the guidelines for granting.
Reviewing/patrolling a page doesn't take much time, but it requires a strong understanding of Wikipedia’s CSD policy and notability guidelines.
Kindly read the tutorial before making your decision, and feel free to post on the project talk page with questions.
If patrolling new pages is something you'd be willing to help out with, please consider applying here.

Thank you for your consideration. We hope to see you around!

MediaWiki message delivery (talk) 15:21, 22 February 2024 (UTC)[reply]

CS1 error on Kavalactone

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CS1 error on Artificial photosynthesis

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Nitrilotris(methylenephosphonic acid

Hello Smokefoot; I was passing by this redirect that did not look wholly correct to me, and wanted to ask whether the missing closing bracket on this redirect was intentional? No redirect currently exists with the closing-parenthesis, so this could possibly be moved there if that was the intention. Thanks, Utopes _{(talk / cont)} 14:37, 1 March 2024 (UTC)[reply]

Thank you for catching that issue. It has been repaired. --Smokefoot (talk) 14:21, 2 March 2024 (UTC)[reply]

"Nitrilotris(methylenephosphonic acid" listed at Redirects for discussion

The redirect Nitrilotris(methylenephosphonic acid has been listed at redirects for discussion to determine whether its use and function meets the redirect guidelines. Anyone, including you, is welcome to comment on this redirect at Wikipedia:Redirects for discussion/Log/2024 March 3 § Nitrilotris(methylenephosphonic acid until a consensus is reached. Utopes _{(talk / cont)} 17:46, 3 March 2024 (UTC)[reply]

Chlorosalicylic acid

I'm deeply disappointed that you created Chlorosalicylic acid but did not fully develop the topic. As you know, the main namespace is not for drafts. You could have used a user sandbox for this. Wikipedia is not the wild west that it might have been twenty years ago. Chris Troutman (talk) 19:20, 10 March 2024 (UTC)[reply]

Like recent specialized publications on topics one doesnt understand? Try these on

See User talk:Jwdietrich2#Like recent specialized publications on topics one doesnt understand? Try these on for details. Jwdietrich2 (talk) 20:50, 23 March 2024 (UTC)[reply]

Edit summaries

Thanks for your addition to Isononyl alcohol, but please be careful not to use a misleading edit summary. Your summary referred only to changing a reference. PamD 04:23, 4 April 2024 (UTC)[reply]

Cobalt(II) chlorate image

Yikes, that was indeed poor. I removed it from other-languages' Wikipedia articles, and it will be deleted altogether off Commons next week. DMacks (talk) 20:27, 6 April 2024 (UTC)[reply]

Manganese compound

Smokefoot, i replied to your recent post on Talk:Pentacarbonylhydridomanganese. Solomonfromfinland (talk) 18:28, 9 April 2024 (UTC)[reply]

Thiazolone moved to draftspace

Thanks for your contributions to Thiazolone. Unfortunately, I do not think it is ready for publishing at this time because it has no sources. I have converted your article to a draft which you can improve, undisturbed for a while.

Please see more information at Help:Unreviewed new page. When the article is ready for publication, please click on the "Submit your draft for review!" button at the top of the page OR move the page back. JoeNMLC (talk) 18:52, 18 April 2024 (UTC)[reply]

Titanocene dicarbonyl

Hi, I saw you reverted my addition of the factoid in Titanocene dicarbonyl. Of course, it is. But as the named elements were no links, the reason why the compounds are related remaines to the not to much fact based reader rather obscure. I changed the names of the elements into links. I hope the contribution now is able to please you. T.vanschaik (talk) 09:32, 30 April 2024 (UTC)[reply]

Thank you for your message. "Titanium is the lightest element in group 4, zirconium and hafnium are just heavier members there in." is just inappropriate. Happy editing and keep up the good work. --Smokefoot (talk) 13:22, 30 April 2024 (UTC)[reply]

Your submission at Articles for creation: Thiazolone has been accepted

Thiazolone, which you submitted to Articles for creation, has been created.

Congratulations, and thank you for helping expand the scope of Wikipedia! We hope you will continue making quality contributions.

Since you have made at least 10 edits over more than four days, you can now create articles yourself without posting a request. However, you may continue submitting work to Articles for creation if you prefer.

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Thanks again, and happy editing!

asilvering (talk) 18:22, 6 May 2024 (UTC)[reply]

about Split proposal of Cytochrome P450

Maybe put CYPome as a separate page would be a good solution, referring to all CYP genes of a particular species or population? Meanwhile, P450-containing systems can be used to store more information about enzyme architecture and machinery and mechanism. Htmlzycq (talk) 08:11, 11 May 2024 (UTC)[reply]

Making Tetrachloroethylene a Good Article

Background: I mainly work on the Turkish Wikipedia, I have expanded the Turkish article for tetrachloroethylene (which is larger than twice of the English article in size) and nominated it as a Featured Article there. I plan to translate sections from that article to English and nominate the English article for Good Article status. It can require complete rewriting of sections but I don't it'll be an issue since I already have material to add. What do you think? ⲔⲖⲞⲢⲠⲒⲔⲢⲒⲚ (talk) 19:59, 16 May 2024 (UTC)[reply]

@ⲔⲖⲞⲢⲠⲒⲔⲢⲒⲚ: I will try to support your efforts. Here are my initial comments on the article:

It is (hopefully) not important to make the article long to make it FA.
Some editors attracted to the FA nomination will know little chemistry but such outsiders tend to be chemophobic (and chemo-ignorant). So, it will be important to document that it is not so awful. One of the main reasons that it is popular as cleaning agent is that it is nontoxic. Unlike soap and classical detergents, TCE is mostly recycled.
Nonetheless, it could be useful to find info on biodegradation pathways and rates. I am sure that many dry cleaners dumped a lot of this stuff into the ground.
Although not combustible, we might look for its reactions upon incineration (inevitably HCl and CO2).
I will look for some chemistry (reactions) of this stuff.

--Smokefoot (talk) 20:39, 16 May 2024 (UTC)[reply]

You can check out the Turkish article via a translator program, it can give you an idea of what I've written. I did an extensive research on its history and old nomenclature.

In the TR article, I addressed the toxicity and possible carcinogenicity of PCE. I clarified the IARC classification with comparison to another materials classified 2A ("probably carcinogenic to humans") such as red meat and hot beverages (which the readers would be exposed on a nearly daily basis), so the readers can understand it better.
I added some information on its biodegradation, referred to pollution briefly.
I added the products of its pyrolysis and its other reactions there.

I will do the translation, but I might need help on formatting (esp. the citations).

ⲔⲖⲞⲢⲠⲒⲔⲢⲒⲚ (talk) 21:11, 16 May 2024 (UTC)[reply]

"Potassium heptafluoroniobate" listed at Redirects for discussion

The redirect Potassium heptafluoroniobate has been listed at redirects for discussion to determine whether its use and function meets the redirect guidelines. Anyone, including you, is welcome to comment on this redirect at Wikipedia:Redirects for discussion/Log/2024 May 21 § Potassium heptafluoroniobate until a consensus is reached. DMacks (talk) 15:13, 21 May 2024 (UTC)[reply]

CS1 error on Lidia Vallarino

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Nonmetal FAC #9

Good day Smookfoot. I know you're not a fan of this article as FA because you're not a fan of classifications within chemistry. That said, I'm asking all the folks who commented on FAC #8, and that includes you.

Are you able to comment on this nomination(?); there's no obligation. Regards, Sandbh (talk) 03:40, 29 May 2024 (UTC)[reply]

CS1 error on Alan S. Goldman

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Pidgeon process image

Hello Smokefoot. Can you comment on the mistaken inclusion of

in the Pidgeon process article? I'm curious why would one associate Galvanic corrosion with a Magnesium process. Maybe you see an idea floating around in the aether that needs enunciation and then development. Cheers, Stickhandler (talk) 19:25, 11 June 2024 (UTC)[reply]

Azo, diazo?

Hey,

This is an old image of yours and it's currently states that the final compound is diazomethane - but it's showing the wrong structure, should be CH₂ and a negative charge somewhere (carbon preferably). My old copy of March tells me that aliphatic diazonium compounds are highly unstable - though admittedly that is a relative concept in this instance.

Metabolic activation of the nitrosamine NDMA

. Project Osprey (talk) 00:00, 19 June 2024 (UTC)[reply]

Oh, I corrected the figure. Thank you very much, mate. --Smokefoot (talk) 04:03, 19 June 2024 (UTC)[reply]

Apologies. The image was correct, it was the caption that was wrong. See this review (doi:10.1021/acs.joc.0c02774) Project Osprey (talk) 11:13, 21 June 2024 (UTC)[reply]

I'm a little surprised that methyldiazonium is such a weak acid, given how selective diazomethane is for being protonated by various acid groups and the usual route for lab-prep of diazomethane. DMacks (talk) 12:30, 21 June 2024 (UTC)[reply]

Although I have made diazomethane a couple of times, its chemistry always perplexed me. Apparently it can be lithiated. And then there is tmsCHN2 which somehow gives the same products as diazomethane. I guess that its ability to methylate involves protonation to give methyldiazonium?

I reverted the image so that it gives methyldiazonium. The JOC paper is useful.--Smokefoot (talk) 14:01, 21 June 2024 (UTC)[reply]

I once worked with a guy who developed an industrial process that used it. His OPR&D paper is in the diazomethane article (though not by my hand) - He had stories. Apparently the explosive limits reported in the literature varied too much for his liking, so he conducted his own studies at a multi-kilo scale (on a military site), so as to be sure. Made a big bang.

Single carbon compounds always seem to have anomalous properties, often usefully. The aqueous pK_a of methanediazonium ([CH₃N₂]⁺) is estimated to be <10 (doi:10.1039/C6CC03561B) so its not really acidic.

I don't really understand why you can't just make it in-situ the same way you make all the other diazo compounds: methylamine, nitrite and acid? Project Osprey (talk) 15:11, 21 June 2024 (UTC)[reply]

Regarding the TMS analog, our article does indeed note "When used as a reagent in organic synthesis to convert carboxylic acids to their methyl esters, trimethylsilyldiazomethane undergoes acid-catalysed methanolysis, forming diazomethane in situ.[8]". I think I only made diazomethane once, just cookbooking with Aldrich's kit to avoid boom. The Org. Synth. prep using diazald does mention several routes from methylamine.[1] DMacks (talk) 17:05, 21 June 2024 (UTC)[reply]

Well, doi:10.1002/anie.200702131 provides an alternative TMSCHN2 mechanism. Someone should update our article:) DMacks (talk) 17:27, 21 June 2024 (UTC)[reply]

Did it. DMacks (talk) 18:11, 22 June 2024 (UTC)[reply]

So I turned methyldiazonium into a real article. DMacks (talk) 17:46, 21 June 2024 (UTC)[reply]

CS1 error on N-Methylformamide

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A barnstar for you!

	The Original Barnstar
	Smokefoot is very friendly to new users and spreads the knowledge of citation and image addition. Pygos (talk) 09:26, 29 June 2024 (UTC)[reply]

CS1 error on 2,3-Butanediamine

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Editor experience invitation

Hi Smokefoot :) I'm looking for experienced editors to interview here. Feel free to pass if you're not interested. Clovermoss🍀 (talk) 17:31, 1 July 2024 (UTC)[reply]

CS1 error on Fausto Calderazzo

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Question

Since you are the top contributor of Wikipedia talk:WikiProject Chemistry Will you answer a query of mine. The background is in Mark viking's talk page. Basically I want to know which publisher(s) write the best chemistry books. Solomon 7968 10:20, 22 July 2024 (UTC)[reply]

I am not an expert on this matter but here are some perspectives. In terms of money-making, there is intense competition for high school and introductory college chemistry texts. My recollection is that the top sellers have something like 4-5% market share, i.e. there are a lot of choices. Many publishers are in that market because it it lucrative (and somewhat generic). We wiki-editors rarely pay much attention to these sources, it seems. Also, chemists and wiki-editors pay little attention to the publishing house, but to the authors. For more advanced topics, such as inorganic (my area), organic, analytical, biochem, pchem .... there are iconic authors/books in US-Canada, and different iconic sources in UK, and yet another set in Western Europe.--Smokefoot (talk) 13:44, 22 July 2024 (UTC)[reply]

Question

Hello. Can I copy the tables and instructions for the chemical formula template on your user page to use in my user subpage (in another language wiki)? I find it very useful. Thanks. Necatorina (talk) 12:34, 26 July 2024 (UTC)[reply]

Of course. --Smokefoot (talk) 15:38, 26 July 2024 (UTC)[reply]

Speedy deletion nomination of Template:NMR spectroscopy

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Hello, and welcome to Wikipedia. This is a notice that the page you created, Template:NMR spectroscopy, was tagged as a test page under section G2 of the criteria for speedy deletion and has been or soon may be deleted. Please use the sandbox for any other test edits you may want to do. Take a look at the welcome page if you would like to learn more about contributing to our encyclopedia.

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Good Article Reassessment (GAR)

Thanks for your comments on the Wikipedia:Good article reassessment/Zirconium/1 regarding the GAR process started by @Z1720. I'm starting to get the hang of them. I don't have anything in principle against quality reviews but the GAR process is very mysterious. Why Zirconium? Is it the worst GA in the Elements? Easiest to fix? Random? I think the reviews could start with a standard header explaining the positive case for such reviews, eg "To maintain quality across Wikipedia random/periodic/regular/occasional reassessments are applied to WP:Good articles."

The GAR process disproportionally affects a few editors. The original editors that chose to invest in the Good Article Nomination are often not around. The issues are rarely copyediting and mostly things that require a breadth of knowledge on the topic and time to find or reread references. The formal, full-process critique of the article somehow seems more damning than the same comment on the article's Talk page. And the normal rule on Wikipedia of no deadline does not apply. I think these are some of the reasons the process is often resented. Johnjbarton (talk) 17:30, 11 August 2024 (UTC)[reply]

CS1 error on Holmium acetate

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CS1 error on Transition metal perchlorate complexes

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CS1 error on Transition metal azide complex

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Acyl substitution

It's a fundamental reaction type and key mechanism. "Nucleophilic acyl substitution" in particular might not merit an article (it's arguable whether this specific mech has enough to stand apart from a unified discussion with the acidic/electrophilic variant). But for example this edit should link to something rather than nothing. DMacks (talk) 13:52, 26 August 2024 (UTC)[reply]

Ok point taken. For the majority of the cases, "nucleophilic acyl substitution" seems to be jargon that would inhibit readability.

Maybe I am dreadfully wrong.

I dont think that ester hydrolysis requires the term nucleophilic acyl substitution. But maybe I should reinstate a simple article on the topic. The previous version was so redundant with respect to many articles we have on esters, amides, acyl chlorides. Your thoughts welcome.

--Smokefoot (talk) 14:00, 26 August 2024 (UTC)[reply]

The term "nucleophilic acyl substitution" is not used in

March's "organic chemistry"
Anslyn and Dougherty's Modern Physical Organic Chem
Lowry & Richardson's Mechanism and Theory in Organic Chemistry
IUPAC
the only review that has that term in its title "Molecular design of novel activated carboxylic acid derivatives for nucleophilic acyl substitution" By: Imai, Yoshio; Ueda, Mitsuru, Yuki Gosei Kagaku Kyokaishi (1981), 39(4), 312-21 | Language: Japanese

My conclusion: "nucleophilic acyl substitution" is fabricated jargon. --Smokefoot (talk) 18:29, 26 August 2024 (UTC)[reply]

I've seen "nucleophilic acyl substitution" used only in two contexts, both to emphasize one variant of acyl substution vs another. First, as the two-step addition–elimination mechanism (what everyone usually just calls "acyl substition") from Friedel–Crafts or similar mechanisms that go through an acylium intermediate. Second, for acyl substitution (the traditional meaning) that occurs under "basic" vs "acidic" mechanisms. That latter is a useful distinction, because it avoids conflating Brønsted–Lowry concepts with the key "nucleophilic attack" (strong enough Lewis base even if not strong B–L base). But I don't usually hear the acid-catalyzed variant called "electrophilic acyl substition". And it's all a continuum anyway...all you need is "enough" reactivity from any combination of nucleophile and electrophile, and either or both can be pre-activiated.

So I agree that we probably don't need a stand-alone article on the basic (or nucleophilic) variant. DMacks (talk) 07:10, 29 August 2024 (UTC)[reply]

Thanks for the perspective. My agenda, to some extent, is to minimize article titles that do not correspond to recognized terms. I mean, we kinda know what nucleophilic acyl substitution would be, as you imply, but no one uses that term. This agenda is part of a broader agenda that Wikipedia often has too many articles on overlapping subjects. Overlap is inevitable and even desirable, but eventually its too much. And thank you for tidying up some of my work post- nucleophilic acyl substitution, as in the Cannizzaro reaction. ---Smokefoot (talk) 13:50, 29 August 2024 (UTC)[reply]

The only time I hear It's definitely not an exactly-defined phrase in textbooks .

Wikipedia:Isobutyric anhydride

Hi Smokefoot, I think you meant to move this to mainspace. S0091 (talk) 17:10, 28 August 2024 (UTC)[reply]

Polyphenols research

Thought I should discuss this further with you. What in this section seems out of kilter to you? Zefr (talk) 04:19, 29 August 2024 (UTC)[reply]

Tetrachloroethylene

After the recent edits, I am convinced that some American governmental organisation is somehow involved in this article to portray the chemical as a "toxin". US EPA and CDC aren't much reliable in toxicity matters, they are government organisations. Using American governmental/state sources should be against WP:NPOV.

This chemical has been widely used for over 70 years. if it was as bad as people insist, it would have been banned already. The chemical safety standards were way worse than it's now and even then, carbon tetrachloride's use lasted less than perc. As a recent example, n-propyl bromide was introduced into dry cleaning as an alternative to perc but its use didn't even last 20 years because of its toxicity (nPB wasn't even too toxic). Necatorina (talk) 00:37, 24 September 2024 (UTC)[reply]

@Necatorina and Zefr: Hey, I am a big fan of Zefr, but I dont agree with him on this issue. Here is a quote from the current article "As an anthelmintic, tetrachloroethylene was given orally to approximately fifty thousand people between 1925 and 1943. The most severe side effects were nausea and vomiting due to the gastric tract irritation. Most reported poisonings were manifestations of its narcotic effects.<ref name=foot1943>{{cite journal |first1=Ellen B. |last1=Foot |first2=Virginia |last2=Apgar |author-link2=Virginia Apgar |first3=Kingsley |last3=Bishop |title=Tetrachlorethylene as an Anesthetic Agent |journal=[[Anesthesiology (journal)|Anesthesiology]] |date=May 1943 |volume=4 |issue=3 |pages=283–292 |s2cid=70969652 |doi=10.1097/00000542-194305000-00009 |doi-access=free}}</ref>" The opening paragraph relies on a 1950's source. And if this stuff were so bad, you can be sure that environmentalists would be marching in the streets. --Smokefoot (talk) 01:53, 24 September 2024 (UTC)[reply]

Why are people pushing the narrative that tetrachloroethylene is toxic and carcinogenic? From what I have read, it is simply uncertain. Necatorina (talk) 02:25, 24 September 2024 (UTC)[reply]

It's not only limited to tetrachloroethylene, there's a hate/fear mongering towards organochlorides and also chlorine itself. Government organisations, institutions and mainstream media amplify it. People would rather believe what higher-ups ("respected organisations") say than to do their own reading. Necatorina (talk) 02:32, 24 September 2024 (UTC)[reply]

Government organizations are among the highest standard of sourcing in mainstream science and on Wikipedia, especially for medical topics like toxicity of chemicals implicated as carcinogens and dangerous to mothers and children. See WP:MEDORG and WP:MEDASSESS where national guidelines (i.e., governments and clinical agencies) are among the highest quality of medical sourcing.

Smokefoot - I cited the 2020 EPA toxicity profile (which is on the CDC's website, so apparently approved and endorsed by the national disease center), and tetrachloroethylene is on the UK's chemical hazard list and Canada's toxin list. Many other national centers with warnings could be cited.

One could readily choose from more than 100 publications on tetrachloroethylene toxicity. The chemical is obviously on the radar for consumer protection, health advisories, and need for more research - proving high morbidity for a toxic substance is obviously not easy research to do. Zefr (talk) 03:01, 24 September 2024 (UTC)[reply]

If it's so bad, why is it still widely used in most first world countries? Is the dry cleaning industry trying give us all cancer... or maybe it isn't bad at all? No, no it really is very carcinogenic and neurotoxic, why would governments lie to us? I stand corrected. I hope Necatorina listens to us and stops defending such a toxin. 141.196.10.2 (talk) 08:49, 24 September 2024 (UTC)[reply]

I dont know, why is hydrazine still legal? "Tetra ethyl death" as some in the industry call it? Formaldehyde? N-Nitrosodimethylamine? Get over yourselves 76.119.108.221 (talk) 09:22, 24 September 2024 (UTC)[reply]

Hydrazine is extremely toxic and is only handled by professionals in PPE, you can use tetrachloroethylene at home with no protection and be fine. Tetraethyllead causes brain damage from lead poisoning, I don't remember anything with cancer, it's not a chlorinated compound either. Formaldehyde is very reactive and it causes cancer in humans because it reacts with biochemicals, tetrachloroethylene is mostly unreactive in human body and there is no proof that its metabolites cause cancer either. N-Nitrosodimethylamine mostly causes cancer from DNA damage. Tetrachloroethylene and its metabolites do not damage the DNA.

This is the worst whataboutism I've read in a while. None of the chemicals you listed have anything in common with tetrachloroethylene. While there's toxicological difference between chlorinated solvents, how can you give unrelated compounds as examples? There's no solid proof that tetrachloroethylene causes cancer, there's no logical mechanism for that. I'm not denying the negative effects such as strong anaesthetic effect upon and environmental controversy, just tetrachloroethylene isn't carcinogenic and it has low toxicity. Necatorina (talk) 10:09, 26 September 2024 (UTC)[reply]

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