User talk:Smokefoot/TalkArch2017

Chlordane

The editor Racassidy54 appears to have a significant interest in his topic. See http://toxfree.net/chlordane/Cassidy/index.php. JSR (talk) 20:32, 6 January 2017 (UTC)

H2S3 geometry

I completely agree with this edit about the geometry of trisulfane. Is this NIST site a reliable source? The geometry looks similar to one in our reliably cited trioxidane article. DMacks (talk) 15:43, 6 February 2017 (UTC)

I apologize for the snarky edit summary. Sort of bugs me that some are so keen to enhance the hydrogen chalcogenide article with fluffy stuff about H₂Po and water being a toxic at high concentrations, but don't seem to take the time to learn the basic preference for the 90 degree dihedral. I cannot presently access the NIST site. I did find DOI 10.1007/b13182, which indicates 90 SSSH dihedral for C2 and Cs-symmetrical rotamers of H2S3. My guess is that H2O3 is similar since H2O2 has a big dihedral. I guess we should reinspect the parent H2Sx and H2Ox articles as you suggest.--Smokefoot (talk) 17:30, 6 February 2017 (UTC)

Reference errors on 7 February

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With regard to the JTe discussion

As I said on the Talk page of the individual posting the 43,000 byte edit, I do not think this carte blanche article replacement can be allowed to stand, but not for reasons that have led others to object (e.g., disrespect of WP process, or overtechnicality of the posted product). Its accuracy/precision to the subject is its best point, and one can always bring the level down from where that 43K bytes of content places it. However, it cannot stand as a "just trust us" piece of work, with section after section of unsourced content.

I would therefore propose that you, Smoke (as you began the questions over this) move the 43K byte edit to Talk, in a collapsed entry in a new section, with a short intro, calling for its use as a basis for introducing revised sections into the article, a section at a time, with each edit demanding that references for the content being in place before the new section is introduced.

This accomplished both purposes—a respectful, slow and steady transition of the article from past to future (much more authoritative, accurate content), and ensuring that the right pattern is set for future, of no content from editors that is not sourced, regardless of their credentials. (The issue for future always being that less able editors following the pattern—of "no need to source"—after the credentialed leave, or change focus.) Reply here? Cheers, Le Prof Leprof 7272 (talk) 04:33, 22 February 2017 (UTC)

About the Jahn Teller effect, those actions are now pretty old and I have kinda forgotten some details. As you can see we removed this massive edit for a week or two hoping to coax the team to return and integrate their edit into its predecessor, but they didnt. So I decided to reinstated their material and weave in some of the older lower level content.

I agree with you that this bulldozing edit by a committee was not desirable. If it were replicated, it could be a bad precedent. The situation was almost unique for the Wiki Chem, and the committee appeared to be operating at a high level. It think that it was a group of professors at a meeting.

Most block replacements are done by grad students egged on by faculty. Such large edits are in fact reverted by me and some others. So far, our small group of editors are effective at preventing large over-writing projects. Increasingly, these student projects are being forced into almost moronic topics lest their articles receive scrutiny.--Smokefoot (talk) 14:15, 22 February 2017 (UTC)

Sulfuryl Fluoride

in regards to this edit https://wiki.riteme.site/w/index.php?title=Sulfuryl_fluoride&oldid=725498714 you cant just delete things without explaining yourself, please explain why this was removed. The residue may not be "permanent" in the literal sense of "never ending" but if you look at the cited risk charactization document the chemical does leave residue on food and household objects http://www.cdpr.ca.gov/docs/emon/pubs/tac/tacpdfs/sulfluor/final_rcd_vol1.pdf so why did you delete this? Can you please edit the wikipedia page to include this information on this chemical Meaningzone (talk) 19:47, 9 March 2017 (UTC)

Hi there. You are taxing my memory, since it has been a while. I can see that it looks like someone was slipping in terms like "acute neurotoxin" into the lede paragraph, which is pejorative or conspiracy theory talk for a compound fairly widely used to fumigate homes. A statement that began "MIT-based study" is appealing to some sort of US-oriented authority - most of the world does not give a hoot about MIT-based anything. Other things that I typically go after are country-specific orientation (Wikipedia is global), ad procedural advice (WP:NOTMANUAL, or medical comments absent WP:MEDRS support. One approach is to reinstate the key components and see what happens. --Smokefoot (talk) 21:48, 9 March 2017 (UTC)

Wikipedia is built on sources, you cant just delete an "MIT based study" because you dont hold them in high regard. They did a study, it happened. You can find some other study that found the opposite but you can't just go deleting things you personally disagree with. You seem like a paid shill by chemical companies to clean up things they disagree with.

Meaningzone (talk) —Preceding undated comment added 19:40, 28 May 2017 (UTC)

Another Candidate for you

Check User:Muhammadshahzadaslam for a prime COI candidate.JSR (talk) 18:58, 30 March 2017 (UTC)

Yep. Maybe the case is so egregious that others will deal with it. --Smokefoot (talk) 17:59, 31 March 2017 (UTC)

Papermaking

just a quick thank you and don't be a stranger :-) This article needs a lot of work, in big and in details, we need to address both, I appreciate your fixes. YamaPlos talk 21:14, 3 April 2017 (UTC)

Water of crystallization

Hi Smokefoot, I have a nomenclature question. How is the following formula pronounced, beside the pentahydrate nomenclature:

• CuSO₄•5H₂O

Copper sulfate times five water/H2O or with five water/H2O or something else? --ZdBdLaLaLa (talk) 09:29, 9 April 2017 (UTC)

Most people call it just "copper sulfate", since 99.9% of the time, one means the pentahydrate. If one wanted to be highly specific, one would say copper sulfate pentahydrate.--Smokefoot (talk) 17:32, 9 April 2017 (UTC)

Dimethyl sulfite

I found Voss also, but sometimes those old preps can have errors. I have also found a current one, saying CH3Cl, but it was a shaky source. I will dig into it tomorrow when I can get a hold of a couple of books. Did too many alcohol conversions with SOCl2 to let that one go. Also favorite trick question in Organic class.JSR (talk) 22:19, 16 April 2017 (UTC)

I'll be interested in what you find. The Germans didnt seem to mess up, they distilled many grams of product as their work up. I will check eEROS, which is very reagent oriented. My initial guess is that usually the ROH --> RCl is carried out relatively dilute, allowing HCl to dissociate to give the nucleophilc Cl-. As you saw, Voss et al also made the chiral MeOS(O)Cl and MeOS(O)OEt. --Smokefoot (talk) 22:54, 16 April 2017 (UTC)

OK, eEROS to the rescue: a couple of quotes from doi 10.1002/047084289X

"Thionyl chloride reacts with primary, secondary, and tertiary alcohols to form chlorosulfite esters.... When thionyl chloride is in excess, or when alkyl chlorosulfites are treated with thionyl chloride, alkyl chlorides are produced ..." Not 100% satisfying, e.g. as to how ROS(O)Cl and SOCl2 react. --Smokefoot (talk) 23:02, 16 April 2017 (UTC)

Cyclohexanedione

Hi Smokefoot. Thanks for creating the article for 1,3-Cyclohexanedione. Can you please double check one statement in it? "It reacts with alcohol to 3-alkoxyenones" doesn't make sense to me. Should it read instead something like "it reacts with alkyl halides to give 3-alkoxyenones"? -- Ed (Edgar181) 15:37, 27 May 2017 (UTC)

yes good catch. I was wondering about that but here is the lead-off statement in eEROS. "The acid-catalyzed reaction of CHD with alcohols affords β-alkoxy enones". The example is isobutanol and then they give an example of a hydrazine doing the same thing. I think that the idea might be that the dione tautomer adds the NuH and then enolization sets in.

Yes, I need to put in the C-alkylation (2-METHYL-1,3-CYCLOHEXANEDIONE A. B. Mekler, S. Ramachandran, S. Swaminathan, and Melvin S. Newman Org. Synth. 1961, 41, 56 DOI: 10.15227/orgsyn.041.0056)

I was also wondering about showing the dione in the box when my reading indicates that dione is minor.

I would like to find the tautomeric equilibria vs acyclic 1,3-diones.

Just in the middle of the whole thing now. --Smokefoot (talk) 15:52, 27 May 2017 (UTC)

Perhaps formation of an acetal followed by elimination? EdChem (talk) 16:33, 27 May 2017 (UTC)

Yes. Acid catalized acetal formation, followed by elimination. I didn't consider that. My mistake - I got stuck thinking it was intended to describe alkylation. -- Ed (Edgar181) 17:23, 27 May 2017 (UTC)

Speedy deletion nomination of Sodium stannite

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Hello, and welcome to Wikipedia. This is a notice to inform you that a tag has been placed on Sodium stannite requesting that it be speedily deleted from Wikipedia. This has been done under section A3 of the criteria for speedy deletion, because it is an article with no content whatsoever, or whose contents consist only of external links, a "See also" section, book references, category tags, template tags, interwiki links, images, a rephrasing of the title, a question that should have been asked at the help or reference desks, or an attempt to contact the subject of the article. Please see Wikipedia:Stub for our minimum information standards for short articles. Also please note that articles must be on notable subjects and should provide references to reliable sources that verify their content.

If you think this page should not be deleted for this reason, you may contest the nomination by visiting the page and clicking the button labelled "Contest this speedy deletion". This will give you the opportunity to explain why you believe the page should not be deleted. However, be aware that once a page is tagged for speedy deletion, it may be removed without delay. Please do not remove the speedy deletion tag from the page yourself, but do not hesitate to add information in line with Wikipedia's policies and guidelines. If the page is deleted, and you wish to retrieve the deleted material for future reference or improvement, then please contact the deleting administrator, or if you have already done so, you can place a request here. Robert McClenon (talk) 03:09, 1 June 2017 (UTC)

I have contested these two (identical) speedy deletion nominations. Robert McClenon, this was not eligible for an A3, it is a redirect page that was blanked by an IP. I have restored to redirect. EdChem (talk) 05:03, 1 June 2017 (UTC)

Speedy deletion nomination of Sodium stannite

If this is the first article that you have created, you may want to read the guide to writing your first article.

You may want to consider using the Article Wizard to help you create articles.

Hello, and welcome to Wikipedia. This is a notice to inform you that a tag has been placed on Sodium stannite requesting that it be speedily deleted from Wikipedia. This has been done under section A3 of the criteria for speedy deletion, because it is an article with no content whatsoever, or whose contents consist only of external links, a "See also" section, book references, category tags, template tags, interwiki links, images, a rephrasing of the title, a question that should have been asked at the help or reference desks, or an attempt to contact the subject of the article. Please see Wikipedia:Stub for our minimum information standards for short articles. Also please note that articles must be on notable subjects and should provide references to reliable sources that verify their content.

If you think this page should not be deleted for this reason, you may contest the nomination by visiting the page and clicking the button labelled "Contest this speedy deletion". This will give you the opportunity to explain why you believe the page should not be deleted. However, be aware that once a page is tagged for speedy deletion, it may be removed without delay. Please do not remove the speedy deletion tag from the page yourself, but do not hesitate to add information in line with Wikipedia's policies and guidelines. If the page is deleted, and you wish to retrieve the deleted material for future reference or improvement, then please contact the deleting administrator, or if you have already done so, you can place a request here. Robert McClenon (talk) 03:11, 1 June 2017 (UTC)

Thanks for taking the time to contact a chemist (me). The article was ill-conceived but I repaired it a couple of years ago. So the article is good.--Smokefoot (talk) 23:51, 4 June 2017 (UTC)

Copying within Wikipedia requires proper attribution

Thank you for your contributions to Wikipedia. It appears that you copied or moved text from Steam reforming into Biohydrogen. While you are welcome to re-use Wikipedia's content, here or elsewhere, Wikipedia's licensing does require that you provide attribution to the original contributor(s). When copying within Wikipedia, this is supplied at minimum in an edit summary at the page into which you've copied content, disclosing the copying and linking to the copied page, e.g., copied content from [[page name]]; see that page's history for attribution. It is good practice, especially if copying is extensive, to also place a properly formatted {{copied}} template on the talk pages of the source and destination. The attribution has been provided for this situation, but if you have copied material between pages before, even if it was a long time ago, please provide attribution for that duplication. You can read more about the procedure and the reasons at Wikipedia:Copying within Wikipedia. Thank you. If you are the sole author of the prose that was moved, attribution is not required. — Diannaa 🍁 (talk) 21:02, 4 June 2017 (UTC)

I have probably copied a lot of content between Wikipedia articles over the previous decade. I would guess that most of the content that I have transferred/copied was a mashup of many editors' contributions, who added a word, a comma, etc. The other complication is that I modify almost everything that I "copy." I will study your suggestion and strive to be careful in the future. Perplexed and surprised, --Smokefoot (talk) 23:48, 4 June 2017 (UTC)

Here's another example: Yesterday you moved content from the article Abramov reaction to create the new article Pudovik reaction. Your edit summary says "split off", but proper attribution requires tht we specify at the destination article what the source article was. ie, "Attribution: content in this section was moved here from Abramov reaction on July 9, 2017. Please see the history of that page for full attribution." Please leave a message on my talk page if you still don't understand what to do or why we have to do it. Thanks, — Diannaa 🍁 (talk) 20:26, 10 July 2017 (UTC)

Oh yes, thanks for pointing out my oversight. I finally figured out what you were getting at last time, whereas I had assumed that content can be reshuffled within Wikipedia without attribution. A more detailed edit summary indicating the source of that content would have been appropriate. Not that it addresses your concerns 100%, but the new article was almost totally re-written so the verbage is almost completely new. If you see other issues, drop me a line. Cheers, --Smokefoot (talk) 22:13, 10 July 2017 (UTC)

Constituents of tobacco smoke

Re Constituents of tobacco smoke

Thanks for the heads up. I will need a little time to articulate my disagreements with the points so far raised at. Wikipedia talk:WikiProject Chemistry#Constituent of tobacco smoke. I believe the issue is equally relevant to Wikipedia talk:WikiProject Health and fitness. You are of course free to start a thread there before I do. Bosley John Bosley (talk) 14:03, 11 June 2017 (UTC)

Just bear in mind, Wikipedia is not an advocacy group. We are do-gooders in that we spread general information in a highly readable format. Wikipedia doesn't nudge people toward what we editors see as healthy lifestyles. We are also mindful of not encumbering articles with minutia in a manner that obscures the main message. So those comments give you a sense of where I am coming from. --Smokefoot (talk) 14:09, 11 June 2017 (UTC)

As you know I disagree with elements of your approach. I have raised a suspicion at Wikipedia:Sockpuppet investigations/Smokefoot and feel this need to run its course first. Bosley John Bosley (talk) 16:36, 19 July 2017 (UTC)

OK, you can see that I have brought this topic up again at the chemistry project talk page, which seems to be the appropriate forum. I will offer this advice if you are not a chemist, physical reality is all chemical, everything - computers, cig smoke, whisky, bananas, road pavement, trees, ... and most of these things are composed of a very long laundry list of chemicals, including good, bad, and ugly ones. I know this statement can seem preachy (an accusation that has been leveled at me before). Chemists could fill all of the articles with chemical information, but we choose not to for reason of clutter and WP:UNDUE.

Thank you for reminding me of what I was told in the first minute of my very first chemistry lesson - apparent kindness which betrays a feeling of superiority - patronising is a better description but hey I'm not telling you anything that you don't know already and I suspect I will continue to receive your friendly advice. Per WP:UNDUE avoiding giving undue weight means that articles should not give minority views... as detailed a description as more widely held views. What constitutes tobacco smoke is not a minority view and WP:Undue has no relevance. Chemists could fill all of the articles with chemical information, but we choose not to for reason of clutter...and I always thought it was because they had better things to do.Bosley John Bosley (talk) 23:48, 19 July 2017 (UTC)

Just curious, not to mention slightly flattered, whom would I be a sockpuppet for or with? --Smokefoot (talk) 17:41, 19 July 2017 (UTC)

Hey it was only fair to let you know that I know. Bosley John Bosley (talk) 23:48, 19 July 2017 (UTC)

No problem. Hopefully I can get some discussion on the topic we are debating. Cheers, --Smokefoot (talk) 03:08, 20 July 2017 (UTC)

Regarding cyclopentadienyl complex

I think the examples of and information regarding cyclopentadienyl complexes of different hapticities should be kept. OrganoMetallurgy (talk) 00:09, 15 June 2017 (UTC)

I will follow your suggestion and take another crack at addressing gaps or bad deletions. Like I said in the edit notes, my impression was that the section was redundant and had crossed the line in being a textbook. Your comment is very welcome. With best wishes. --Smokefoot (talk) 02:36, 15 June 2017 (UTC)

Old merge proposal

Hello! I noticed your somewhat old merge proposal at Dodecenyl succinic anhydride. It appears the merge is uncontroversial. Any chance you'd be willing to complete the merge? I'd do it myself, but tragically my chemistry knowledge is pitiful and I'm not sure where to stick the info in Dodecenyl succinic anhydride. Thanks a bunch! Happy editing! Ajpolino (talk) 03:51, 15 June 2017 (UTC)

OK I did it. Thanks for the reminder. --Smokefoot (talk) 13:07, 15 June 2017 (UTC)

Thanks a million! Ajpolino (talk) 22:56, 19 June 2017 (UTC)

Edits to Sodium Iodide

Smokefoot, I strongly suggest you verify the information that I added about sodium iodide, and how it is not the added nuitrition that people think it is in that section. currently the section has only once sentence saying that potassium iodide is added to sodium chloride, table salt. I have cited my sources correctly. Please review those sources before completely removing my editions. I am willing to change some of the wording with you, but I believe that information is pertinent, relevant, and necessary in that article. I am willing to get other experts involved in this edit as well. Thank you for your concern. And no, iodine is not the same as iodide, it depends on the other element that it is attached to. Added potassium iodide in sodium chloride table salt does not prevent serious thyroid iodine deficiencies, which are caused by fluorides and chlorides added into drinking water. in the very next section of the article it uses that exact chemical equation i just described to prove that happens. the sources I cited are true and correct, and are used for medical purposes. Please review the sources, including the book not just the websites. Thank you. D.nungesser (talk) 16:41, 19 June 2017 (UTC)

Cycloheptatrienyl

I'm not sure that it's ever particularly accurate to say it acts as a cationic 6 electron donor, but I could be wrong about that. OrganoMetallurgy (talk) 01:46, 21 June 2017 (UTC)

OK, I was unaware of anyone attributing CHT^3-, but I see your point. The usual view is 6e, as in the classic [Mo(CO)₃(eta-7-CHT)]⁺. But these assignments are somewhat artificial.--Smokefoot (talk) 03:26, 21 June 2017 (UTC)

Here's a pertinent paper doi:10.1021/ja00084a045 Nature of the Cycloheptatrienyl-Transition Metal Bond. A Study of Electron Distribution in the Mixed-Ring Sandwich Molecules [Ti(η-C₇H₇)(η-C₅H₅)], [Nb(η-C₇H₇)(η-C₅H₅)], [Ta(η-C₇H₇)(η-C₅H₅Me)], and [Mo(η-C₇H₇)(η-C₅H₅)] by Photoelectron Spectroscopy with Variable Photon Energy.--OrganoMetallurgy (talk) 18:49, 25 June 2017 (UTC)

OK, that's what I thought it would be. Thanks. --Smokefoot (talk) 20:37, 25 June 2017 (UTC)

I have unreviewed a page you curated

Hi, I'm Robert McClenon. I wanted to let you know that I saw the page you reviewed, 1,4-Diazacycloheptane, and have un-reviewed it again. If you have any questions, please ask them on my talk page. Thank you.

Robert McClenon (talk) 14:42, 24 June 2017 (UTC)

@Robert McClenon: Not sure I understand the message, but do let me know if you have any comments on the article. There are actually two related articles that I have written recently. Cheers, --Smokefoot (talk) 15:20, 24 June 2017 (UTC)

Wanted to let you know that I'd retired

Thank you for earlier affirming interactions. See User:Leprof_7272 page for details if interested. Bonne chance. Le Prof 73.210.155.96 (talk) 16:09, 24 June 2017 (UTC)

Collaboration suggestion

Hi

To be honest the "lone wolf" culture of wikipedia is starting to drag a little (no intention of quitting though loads of stuff needs editing). I know you are interested in chemistry related articles, so may I suggest a collaborative effort to improve the article QM/MM? I've never done a collaboration before and it would be fun to give it a go. EvilxFish (talk) 13:32, 28 June 2017 (UTC)

@EvilxFish: Hi. I cant help, mainly because I am ignorant of electronic structure and even weaker on calculations. I am also a hot-and-cold editor, depending on my time and mood. If you have any conventional chemistry areas, I am usually available to help. --Smokefoot (talk) 19:20, 28 June 2017 (UTC)

@Smokefoot: No worries, I am also working on the Electron paramagnetic resonance page, I am focusing on the Hardware components section however there is plenty that needs editing there if that is more your area. Also just a quick Q, I think this page Actinide chemistry should be merged into Actinide what do you think? EvilxFish (talk) 22:57, 28 June 2017 (UTC)

Would you mind taking a look at one of my drafts?

Draft:pentafluorosulfanylbenzene is the one. OrganoMetallurgy (talk) 15:03, 3 July 2017 (UTC)

@OrganoMetallurgy: Well its your own work and it is "dangerous" to ask me for advice because I am opinionated. If you have thick skin, my main advice is for the kick-off sentence where I tend for blandness giving classification, always preference for vernacular name (vs formal), and a structural formula (vs the empirical one in the box)

Pentafluorosulfanylbenzene, also known as phenylsulfur pentafluoride, is a colorless liquid with high chemical stability. Phenylsulfur pentafluoride, formally known as pentafluorosulfanylbenzene (no real chemist calls it that, only smart high school teachers and IUPAC bureaucrats), is an organosulfur compound with the formula C₆H₅SF₅. your comments on stability and color etc as before. Otherwise it is a good topic and nifty compound. We wrote up SF₅Cl a number of years ago. I try for find something secondary, an application (probably none in this case), your historic ref to AgF2 method is instructive. Maybe pt gp symmetry. Maybe you can find a Hammett constant for SF5 substituent. In the US, the expert used to be Joseph Thrasher at Alabama. Of course a lot of Germans are probably all over this area. --Smokefoot (talk) 22:03, 3 July 2017 (UTC)

I'm not all that interested in phenylsulfur pentafluoride in and of itself, but I made the draft because I'm working on an article on the pentafluorosulfanyl group and thought there should probably an article on the parent arylsulfur pentafluoride. There isn't that much infomation about it, which is why I only cited primary sources, but I'm planning on making a page about its nitrated derivatives, which have been studied far more due to their greater accessibility and reactivity. Also it is my understanding that the term pentafluorosulfanyl has become more popular recently and that the name pentafluorosulfanylbenzene would be the more common modern term. OrganoMetallurgy (talk) 22:38, 3 July 2017 (UTC)

I agree that the SF5 group is an even better topic, in which case you dont need a chembox. Here is probably the top source: DOI:10.1021/cr500336u.ChemRev is usually unbeatable.--Smokefoot (talk) 22:55, 3 July 2017 (UTC)

Yeah, I've been reading it the past couple days. Also the pentafluorosulfanylbenzene draft is completely separate from the one about the SF₅ group. OrganoMetallurgy (talk) 23:13, 3 July 2017 (UTC)

With a recent Chem Rev, one barely needs to cite any other narrower source, perhaps citing the original first this or that I guess. --Smokefoot (talk) 03:50, 4 July 2017 (UTC)

I'd also like it if you could occasionally take a look at my drafts/ideas for articles as can be found at User:OrganoMetallurgy/Drafts/. I don't know if you're interested in any of the stuff there, but if you are, I'd appreciate any contributions you can make to any of the topics there. To clarify I'm asking if you're interested in contributing to any of my drafts as well as if you're interested in creating pages on any of the topics listed there, in which case I'd be especially willing to help. OrganoMetallurgy (talk) 22:49, 2 August 2017 (UTC)

OrganoMetallurgy

@OrganoMetallurgy:. I am wiped out for a couple of days. But I made some comments on parts of your to-do list below.--Smokefoot (talk) 05:25, 3 August 2017 (UTC) Tetrathionaphthalene

• you mean Tetrathianaphthalene C10H4S4? good idea. I once either started or planned on an article on perisubstituted naphthalees

Benzenehexathiol

• just a curiousity. no one has done anything striking with it.
• several ttf derivativves, Me2C2E2C=CE2C2Me2
• tetrathiooxalate and esters. No one has done much with them either
• dithiooxalate (DTO) is even more common. Probably an article on its K or Na salt, one used to be commercially available.

Tetrachlorocyclopentadienone precursor to some pesticides

• we have hexachlorocyclopentadiene, but probablyno mention of its complexes

Potassium azodicarboxylate can be used as a precurser to diimide

• good idea

Dithiolium two aromatic organic cations with the formula C₃H₃S₂⁺

• also dmit (C3S52-, also two isomers from CS2 + Na (in Org Syn)

Methanedisulfonic acid. The simplest disulfonic acid.

• dont know how we missed it.
• also some "carbon acids" like CH2(SO2X)2

Hydrocarbons

[2.2]Paracyclophane strained molecule with bent benzene rings

• we have phanephos and cyclophanes, and even a category on cyclophanes.
• agreed we need the 2.2 as standalone, since it is the anchor cmpd.

Organometallic and metalorganic compounds/complexes

Cycloheptatrienyl complexes

• maybe analogous to other articles on "Transition metal complexes of [your ligand here]"

Tris(cyclopentadienyl)dinickel cation, First triple decker sandwich complex

• maybe triple decker sandwich complex, with Werner's Cp3Ni2]+ as the top example.
• same article could point out the extensive polydecker family including the R2C2S2BR' etc-based rings (Siebert ACIE)

Inorganic compounds

Potassium graphite is a graphite intercalation compound that is used as a reducing agent

• spin it out from Graphite intercalation compound

Boranes and related salts/anions

• I am not a big borane fan, oversold area. Norman Greenwood was an enthusiast and his book with Earnshaw is still probably a good foundation.
• we dont have B2H7 anion
• some of the ammoniates (my theme: keep it simple)
• Na2B12(OH)12

Heteroboranes and related salts/anions

closo-Azadodecaborane, NB₁₁H₁₂

• why not just azaboranes?
• borane adducts of phosphines, maybe we have that somewhere, but these get a lot of use.

Functional groups/Ligands

Tris(trimethylsilyl)methyl aka trisyl, a very bulky alkyl ligand/functional group.

• I recommend LiC(tms)3, then list some derivatives
• do we have Me3SiCH2Li?

Different pages for the chemistry of some elements in each of its major oxidation states

Such as Copper(II), Copper(I), Iron(II), Iron(III), Manganese(II), Magnanese(IV), etcetera

• That is a big job coming up where we need some planning on layout and content.
• There is an article on compounds of zinc etc.

Azo Dye structures

Thanks for your note, which I have replied to. It got me thinking about the structures for these dyes and I think in many cases (particularly where intramolecular H-bonding is possible) the structures we're showing are questionable or perhaps confusing. Acid red 88 probably sums it up best; the page has 3 images - each of which show a different structure for the product. I'm guessing there's some truth in all of them, with the azo group allowing a 'crank shaft' like movement of the naphthalene groups, causing it to switch between naphthol/azo and naphthoquinone/hydrazone forms depending on if it can or can't H-bond - but there's no explanation of that on the page. I think that azo dyes could be improved by explaining these photochromic transitions. --Project Osprey (talk) 00:29, 9 August 2017 (UTC)

Yes, I am pretty sure that there is a lot of confusion in the literature. The author of the Pigment Yellow 10 X-ray paper, Whitaker, refers to that fact in one of his papers. You might be right that the way to fix the problem would be to discuss the tautomers in a general article. Some steps

• it would be ideal (to me) to find example where the assignments have been made and then corrected
• Split-off azo dyes from azo compound, perhaps.
• Within azo dye we need a classification of the main types, and within each we could point out the structural complexities.--Smokefoot (talk) 00:52, 9 August 2017 (UTC)

Regarding Barium ferrite

I saw you were the one who added the its formula as being BaFe₂O₄ back in 2007, and I'm wondering if you remember why you thought BaFe₂O₄ was the formula. Also there's some other issues that need to be addressed, but I'll wait to mention them until later. OrganoMetallurgy (talk) 19:58, 12 August 2017 (UTC)

@OrganoMetallurgy:. Glad that you caught that mistake. I cannot imagine why I made that stupid error in 2007. I just checked Ullmann's encyclopedia, which confirms your BaFe12O19. Keep up the good work.--Smokefoot (talk) 20:47, 12 August 2017 (UTC)

I did some searching, and it doesn't look like stuff published before 2007 asserts that BaFe₂O₄ is particularly magnetic, so congratulations, you appear to be the originator of the myth that barium ferrite magnets are made out BaFe₂O₄. (I could be wrong since I didn't search all that deeply, but from what I've seen it looks likely.) OrganoMetallurgy (talk) 23:10, 12 August 2017 (UTC)

Benzodifurane (or more accurately o-Benzodifurandione) dyes

Benzodifurane dyes are industrial chemicals with no coverage by Wikipedia, so I thought you might be interested. o-Benzodifurandione is apparently the core structure of some disperse dyes. OrganoMetallurgy (talk) 00:33, 20 August 2017 (UTC)

Yes, good idea. Incorporating this large area into Wikipedia is a massive task, so I appreciate the help. --Smokefoot (talk) 11:32, 20 August 2017 (UTC)

Potassium formate

Hi, my friend.You've deleted my 3D file because the structure doesn't show the atom valence. But the representation is 3D and none file shows valence in 3D files. For example, look at Commons. Let's give our hands and respect our friends works. Judge not to be judged. Please, reconsider your opinion or help me to understand it. Use Wikipedia to make friends and feel happy for being useful, not to persecute and depreciate the works of well intentioned people. Let us unite our efforts and have a harmonious behaviour. Strong hug Claudio Pistilli (talk) 13:31, 23 August 2017 (UTC)

First of all, thank you for your kind message. Best wishes to you as well. Spheres floating in space do not accurately represent alkali metal cation (or any ion). It would be terrible deception if readers were instructed that such spheres have any connection to reality. --Smokefoot (talk) 16:23, 23 August 2017 (UTC)

Aluminium

Hi, I'm wondering why you reverted my edits at Aluminium. While I am not very familiar in chemistry, and the hydrogen energy and Brazilian journal may be bad sources, I don't see why you also removed the rest of the citations. Thanks. Darylgolden^(talk) Ping when replying 02:00, 6 September 2017 (UTC)

I have reverted to before I added those two sources. Darylgolden^(talk) Ping when replying 02:05, 6 September 2017 (UTC)

WP:JAGUAR @Darylgolden: Hi, knowing Smokefoot it is likely you had an issue with WP:SECONDARY. Please note that while reviews are considered as secondary sources, papers in journals are considered primary sources and should hence be avoided. That being said he has made mistakes in the past and it does appear as if he also removed a text book reference which should be fine. EvilxFish (talk) 21:01, 7 September 2017 (UTC)

Some of your structures

Greetings Mr. Smokefoot, So I noticed that you replaced some of the images on pages for nucleotides (I think I hastily reverted the one on cAMP, my bad). I'm personally not terribly picky, but I believe they don't really conform to the Guidelines for structures that some of the higher-ups are really insistent about following. Yes, I do know that the unabridged diagrams are easier to understand, but pretty much every picture of an organic structure follows the ACS formatting. Or maybe not, I really don't know. Sorry if I'm pestering you. IAMGOOMBA (talk) 03:09, 6 September 2017 (UTC)

Hi there. Wikipedia does not report to or follow ACS or any particular scientific organization's rules. Not sure where you get the idea that the AMERICAN chemical society would have any sway over this international program, but I realize your suggestion is well intentioned.--Smokefoot (talk) 13:21, 6 September 2017 (UTC)

A barnstar for you!

	The Tireless Contributor Barnstar
	I bestow this tireless contributor Barnstar upon you, in recognition of your continuous efforts to improve chemistry related articles on Wikipedia. Keep up the good work EvilxFish (talk) 19:42, 7 September 2017 (UTC)

Hey thank you very much for this recognition. I am looking forward to doing still more.--Smokefoot (talk) 01:09, 8 September 2017 (UTC)

Need your input (on something that will interest you)

Hi, Mr/Mrs/Ms/Miss/Dr/Rev Smokefoot I would be most grateful if you chipped in here. They are trying to pass a motion which I oppose as IUPAC gives no guidance on it and it's not something I tend to find in mainstream chemistry textbooks. I know you love setting standards (your recent ROOH vs RO₂H proves that). Hope you decide to get involved so far its level pegging on oppose/support. Much love EvilxFish (talk) 08:59, 11 September 2017 (UTC)

Titanium dioxide nanoparticles

I have created the Titanium dioxide nanoparticle article, and I'd appreciate any improvements or further expansion. I'm curious about your thoughts on the applicability of Template:Chembox to nanoparticles; their properties depend a lot on their specific size and morphology, but they do have some properties as a class, for example NIOSH has a recommended exposure limit for them. John P. Sadowski (NIOSH) (talk) 03:44, 16 September 2017 (UTC)

Experiment on wikipedia, you were right

You could not have guessed better when you wrote about one of the articles created by "Carolineneil": "*Ultra specialized with little effort to contextualize. Reads like a essay from an student who is being forced to contribute to Wikipedia but the supposedly supervising faculty member has not bothered to read or understand policy and standards." [1] It was a group of PhD students who were paid to create Wikipedia articles for an experiment. Broke rules on disclosure of paid edits, single purpose accounts and conflict of interest and in spite of multiple warnings never even bothered to learn Wikipedia citation rules. Many articles never were accepted here. Drew hundreds of administrator actions. Of course, none of this mentioned in the "scientific article" that they wrote about this - of similar quality to the edits here.I asked for the user to get banned, and I think a formal reprimand to the supervisors (one at MIT!) is in place. Antimanipulator (talk) 13:20, 28 September 2017 (UTC)

User(s) got banned for undisclosed paid editing. Would you support me for getting their supervisors and their institutions' ethics committees informed? Antimanipulator (talk) 15:11, 28 September 2017 (UTC)

Yes I will support you. You also see that I think that we should dismantle at least one of their articles. Fake News from MIT. --Smokefoot (talk) 19:17, 28 September 2017 (UTC)

Edits in Carbonation

Hi! You did a major overhaul of Carbonation in April. I can't speak of the quality of your contribution, but you completely removed any mention of carbonated beverages from the page. It broke a lot of links - the page is mentioned in Effervescence, Sparkling wine or even Carbonated water. Could you look into fixing this? 2A00:1028:83A2:F52:B07E:6655:C2A1:934E (talk) 18:47, 4 October 2017 (UTC)

Wiki.J.Sci

Hi, I was wondering whether you might be interested in being an editor for the WikiJournal of Science? It's a journal modelled on the successful Wikipedia-integrated academic journal: WikiJournal of Medicine (www.wikijmed.org). Currently several physicists have joined Wiki.J.Sci's editorial board, but it is hoped that the journal will be open to all STEM topics. It'd mainly involve inviting articles and organising their external peer review.

Also possibly of interest: Shafee, T; Mietchen, D; Su, A (2017). "Academics can help shape Wikipedia". Science. 357 (6351): 557–558. doi:10.1126/science.aao0462.

Anyway, let me know if you're interested. T.Shafee(Evo&Evo)^talk 05:04, 6 October 2017 (UTC)

Titanium bis(acetylacetonato)dichloride

Hi Smokefoot. Normally I can rely on you to write about importance chemicals, but Titanium bis(acetylacetonato)dichloride seems to be very obscure and not common. I can only see few references (Substitution kinetics of biphenol at dichlorobis (acetylacetonato-O, O′) titanium (IV): Isolation, characterization, crystal structure and enhanced hydrolytic stability ; Stereochemistry and lability of dihalobis (. beta.-diketonato) titanium (V) complexes. I. Acetylacetonates. So for this substance I can't find a CAS, pubchem or chemspider number :-). Graeme Bartlett (talk) 06:26, 11 October 2017 (UTC)

Thanks for the note. There are about 120 cites in CAS, but 2-3 RN's. I am waiting for the staff at Scifinder to get back to me on my query on the difference. I will probably go with the RN with a ca 100 cites but wanted to be sure. In terms of notability, the compound is the main acac of Ti, there is some patent work on ethylene polymerization, and several papers. So I anticipate that notability will not be a problem. But give it a few days. If it doesnt pass, we'll kill it. Actually, the main challenge is the multitude of names for this substance. Cheers, --Smokefoot (talk) 13:19, 11 October 2017 (UTC)

I am not looking for a kill, but to get some id numbers for it! Pubchem has a tetra-acac listed as well as an oxy bis-acac, Graeme Bartlett (talk) 21:05, 11 October 2017 (UTC)

{{tps}} The three SciFinder entries I see appear to have different configurations of the ligands. They are all "Titanium, dichlorobis(2,4-pentanedionato-κO²,κO⁴)-", but:

• CAS 42532-19-4 is "(OC-6-12)"
• CAS 16986-94-0 is "(OC-6-22)"
• CAS 17099-86-4 is not further specified

I didn't know this polyhedral symbol notation, but it's defined in Red Book (2005) section "IR-9.3.3.4 Octahedral coordination systems (OC-6)". DMacks (talk) 02:51, 12 October 2017 (UTC)

...which appears to have a typo in the second example of page 182. The first example would be the trans of your compound, and makes sense as OC-6-12, whereas the second is cis, and is also identified as OC-6-12 but would be OC-6-22 according to the description of the nomenclature. None of the CAS#s appear to be for a specific enantiomer (Δ/Λ) of the cis. DMacks (talk) 05:45, 12 October 2017 (UTC)

Dear DMacks: thank you immensely. I guess that I have been mentally lazy over the years and never took the time to deal with this symbology. Now I will take a deeper look. Possibly the last RN is for the mixture of cis and trans. Gratefully --Smokefoot (talk) 13:18, 12 October 2017 (UTC)

@DMacks: Oh, CAS just got back to me: "The two substances have different stereochemistry, which is reflected in their name. RN 17099-86-4 has no stereochem and RN 16986-94-0 is OC-6-22 (cis)." When one does a search for the RN with unspecified stereochemistry, these hits do not include citations obtained when searching for cis stereochemistry. Surprising to me that specified are not subsumed into unspecified. I am going to ask CAS about that too.--Smokefoot (talk) 17:24, 12 October 2017 (UTC)

How exactly did you do the "When one does a search for the RN..." searches with specific (or specifically unspecified) stereochemistry? I just searched by molecular formula and got few enough hits I could manually check each one's details. DMacks (talk) 03:30, 14 October 2017 (UTC)

@DMacks:Well I thought that I saw hits for the cis isomer missing in the hit list of the unspeccified stereochem. But today, I got a note from CAS telling me that unspecified gives all hits. So apparently I was wrong. Here is their message: "When searching a structure in SF with no stereochemistry specified, the search will retrieve results that contain both flat structures as those with stereochemistry." I hope that this addresses your message. --Smokefoot (talk) 03:52, 14 October 2017 (UTC)

Makes perfect sense, thanks. DMacks (talk) 04:23, 14 October 2017 (UTC)

Coenzyme F430

Dear Smokefoot - Apologies for my mistake I made regarding the cofactor F430 page. I've not edited on wikipedia before but I felt the cofactor F430 (also referred to as coenzyme) page needed updating. I was just adding the most relevent and up to date biosynthetic text and relevent citations for this area. I was also trying to edit in the same format as another related tetrapyrrole (https://wiki.riteme.site/wiki/Cobalamin_biosynthesis) so I originally included sections for each enzyme, but your moderation is acceptable. I would also like to further upload a figure for the chemical pathway, please could you advise?

@Gollums revenge:. We try to avoid primary references, at least good editors do. In terms of some advice on drawing for Wiki-Chem:

• The main drawing mistake made by new editors is to include words. Any words. Artwork is used on wiki's in other languages, and words detract from versatility.
• The other advice is the usual ChemDraw skills, i.e. dont re-draw subunits, copy and edit them. Keep it clean. Allign, distribute, watch line width,...
• official rules are here Wikipedia:Manual of Style/Chemistry/Structure drawing.
• Other advice:
  • say something about yourself on your user page. Such information facilitates collaboration.
  • Stick to WP:SECONDARY or WP:TERTIARY. We often endure new editors who want to tell us their hottest new result. Wikipedia doesn't seek hot new results: it is an encyclopedia, not a blog or a news feed WP:NOTNEWS. Feel free to ask questions, I'd be glad to help. --Smokefoot (talk) 20:08, 28 October 2017 (UTC)

Thanks Smokefoot, much appreciated - changed username to Walmercc.

"That is not how chemistry works"

I've got to remember that phrase! ^_^ Double sharp (talk) 04:49, 3 November 2017 (UTC)

Na2S reaction with acidic water!

Needs comments! Sundar.sm (talk) 16:40, 4 November 2017 (UTC)

182.101.52.1

I notice that you reverted all the edits of 182.101.52.1 (talk · contribs · deleted contribs · logs · filter log · block user · block log). I just wanted to let you know that they have apparently returned as 182.101.61.91 (talk · contribs · deleted contribs · logs · filter log · block user · block log) and I've reverted them for essentially the same reasons. Both IPs are only adding links to papers published by the same authors, so it seems to be self-promotion. -- Ed (Edgar181) 15:11, 18 November 2017 (UTC)

Mascara Article-Environmental Effects section

Hi Smokefoot. I noticed that you removed the environmental effects section that I added to the mascara wikipedia page, and I was wondering if I could get your feedback on this section so that it could become an addition to the page. I cited all of my sources for reference. I appreciate your help! Kdeleo1 (talk) 03:04, 28 November 2017 (UTC)

Hi Kdeleo1. Well the good news is that you actually asked someone! Please recommend that your colleagues ask before editing extensively. That is unless they already have experience with Wikipedia policies. The show-stopper for me was to find that you apparently inserted a section on "Methanogenesis Replacement". And then a section that begins "On the other hand when airborne, iron oxides have been shown to harm the lung tissues of living organisms by the formation of hydroxyl radicals, leading to the creation of alkyl radicals. " So I figured you were loading random information. The article is supposed to be an overview of mascara supported by general sources. Your selection of Kirk-Othmer Encyclopedia was good. But otherwise the article seemed to be either random or highly tangential. Remember, Wikipedia is not trying to explain anything. Just present facts, general facts. If your instructor is inactive or inexperienced with Wikipedia, you are at a disadvantage.--Smokefoot (talk) 03:15, 28 November 2017 (UTC)

I was trying to provide an overview of the most common pigments of mascara and some of the reactions in which they participate in the environment because pigments are one of the three basic components of mascara as stated in the first paragraph of the original article. I had hoped this would contribute a more detailed look into one of the ingredients of mascara. Did you come across any inaccuracies in the information? Kdeleo1 (talk) 03:25, 28 November 2017 (UTC)

If you want to present an overview of a pigment, then contribute to the relevant pigment articles. And then guide the reader to those places with a wiki-link. That is what links do. Titanium dioxide is a fairly mature article, parts of which are written and rewritten by PhD-level editors. Probably the same for any iron oxide. Mascara is not the place to discuss these oxides of iron or titanium. Thanks again for asking.

I will say that mascara and related cosmetics (eyeliner, etc) are a great place to contribute because readers are unaware of the technology that supports these materials. Kirk-Othmer and its sister encyclopedia Ullmann's (see DOI 10.1002/14356007.a24_219) are excellent sources. I doubt that one can write more than a few paragraphs on the technology behind Mascara. Hopefully your instructor is grading you on quality of your contribution, not that quantity. --Smokefoot (talk) 03:54, 28 November 2017 (UTC)

Okay, I will do that! I will just add a short blurb in order to link the mascara page to those two pages. I appreciate all of your feedback!Kdeleo1 (talk) 17:15, 28 November 2017 (UTC)

Edits to Environmental effects of substances found in toothpaste

Hi Smokefoot! I recently uploaded an article on the environmental effects of substances found in toothpaste, focusing on silver nanoparticles, which you recently commented on and edited. Are there any specific notes you could offer on how to improve my page? This is a project that has already been edited by my classmates and I thought it was a worthy contribution. I would really greatly appreciate any constructive feedback you have to offer on how I can improve my article and hopefully make it into something that can remain on Wikipedia. Hmorg11 (talk) 04:50, 28 November 2017 (UTC)

The article will probably be removed once your course is complete. @Rlcooklsu: It reads like a essay where the student is being rewarded in proportion to the number of words. I guess the first issue: find a book chapter or a review that focuses on the topic you are writing about. If you cannot find such a source, the article stands on flimsy foundations. It is very unfortunate that your instructor is either unaware of Wikipedia style or uninterested in helping his students.--Smokefoot (talk) 12:50, 28 November 2017 (UTC)

Smokefoot, thanks for your critique. Our goal in this project was to synthesize different pieces of scientific literature pertaining to a topic and use Wikipedia as a way to communicate this issue to the public. Would this be a more effective entry if one or two reputable sources were a consistent reference throughout the paper instead of the several I have listed? I personally thought that because we read through and referenced so much literature that our article had a decent foundation, but if that's not the case I certainly want to fix that. Thanks for your quick feedback! Hmorg11 (talk) 15:32, 28 November 2017 (UTC)

I renamed this to Environmental impact of silver nanoparticles. Because the only material ingredient mentioned in the article is the silver. At least there are sources written on that topic. Wikipedia:Synthesis may apply to what was going on here. As Smokefoot says, let the review articles or books do the synthesising for you. And then you present their ideas to the public on Wikipedia. Writings in this silver nanoparticle topic may mention toothpaste, but there seem to be none just on this toothpaste impact, and in fact it seems that the bigger impact is from other things like cloth. Graeme Bartlett (talk) 22:04, 28 November 2017 (UTC)

Fireworks Edits

Hi Smokefoot, I saw you substantially edited the pollution section of the Fireworks page that was uploaded by a partner in my group project. If you don't mind, can you let us know what issues you had with it? For example, was it formatting issues, or more content based issues? We think the content is well thought out and structured but we'd be interested to hear your opinions on it so that we may possibly work together and edit it for reuploading. Thanks! Rjbujol (talk) 20:27, 28 November 2017 (UTC)

Ask your teacher to help, that is his job. You guys are uploading really crappy stuff. Not your fault really, it takes time and experience to write about these topics and to learn Wikipedia's tone and mission. Hopefully, your instructor will stop asking Wikipedia editors to teach you.--Smokefoot (talk) 20:33, 28 November 2017 (UTC)

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Conjugation in ultraviolet–visible spectrometry

Hi and thank you for commenting at Draft:Conjugation in ultraviolet–visible spectrometry. Do you think any of its contents could be of use if merged into another article? Or is is it all something that we should send on the way down to deletion? – Uanfala (talk) 00:12, 29 December 2017 (UTC)

Thanks for asking. I am not very knowledgeable of the topic, but my preliminary suggestion is to check WP:NOTTEXTBOOK. Your content seems like you are teaching. We just summarize knowledge here. Also, keep the English out of figures, put the words in the caption. On a technical level, you might check Woodward's rules as well as polyene#Optical and chemical properties. Happy editing. --Smokefoot (talk) 13:20, 29 December 2017 (UTC)

Thanks! I haven't written that, it's somebody else's work that I came across while tidying up one drafts-related mess. So I take it that the text won't be reusable/copyable into another article without substantial rewriting then? – Uanfala (talk) 13:39, 29 December 2017 (UTC)

I was only giving suggestions, many editors include English in their figures. And many figures and much text are re-used. We are welcome to poach anything from any other article in Wikipedia. I do it all the time. It is a good idea to mention the article from which you poach in your edit notes.--Smokefoot (talk) 13:45, 29 December 2017 (UTC)