User talk:Smokefoot

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January 2014[edit]

Hi there - thanks for taking out the edits on Iodine value I had made on my tablet - I guess I thought I would get back quicker to do the things I had tried to suggest. Could you have a look and see what you think of the next version - there were some things in my edit which I can only see as being worth keeping such as the spelling of organoi(o)dine compounds - I could not see what the weak chemistry was you mentioned in the reversion comment. I am a high school chemistry teacher trying to make this clear enough for my students to understand Skihatboatbike (talk) 19:52, 13 January 2015 (UTC)

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  • used as a saline laxative to treat constipation or to clean the bowel before a colonoscopy.<ref>[http://wishardhealth.kramesonline.com/Medications/26,1558</ref>

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  • of phosphate to aluminium to sodium. Additionally an SAlP of ill-defined stoichiometry is used (Na<sub>x</sub>Al<sub>y</sub>(PO<sub>4</sub>)<sub>z</sub> (CAS# 7785-88-8).<ref>Lucina E. Lampila "

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  • e.g. [[sodium triphosphate]]. Polymeric sodium phosphates are also well known, these include [[Kurrol’s salt, Graham’s salt, and Maddrell’s salt. Cyclic phosphates are called metaphosphates,

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  • Three families of sodium monophosphates are common, those derived from PO<sub>4</sub><sup>3-</sup>), hydrogen phosphate (HPO<sub>4</sub><sup>-</sup>), and dihydrogenphosphate (H<sub>2</sub>PO<sub>4</

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  • 178873-19-3, and 63148-57-2. These include the tetramer ((MeSiHO)<sub>4</sub>), copolymers of poly(dimethysiloxane and poly(methylhydrosiloxane), and trimethylsilyl terminated materials.

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  • : 2"(MeSiH)" + (Bu<sub>3</sub>Sn)<sub>2</sub>O → "(Me<sub>2</sub>Si<sub>2</sub>O" + 2 Bu<sub>3</sub>SnH

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  • }</ref> The most important additive is [[cornstarch]], although [[potato starch]] may also be used).

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  • are mainly used as [[radical initiator]]s in the [[polymerization]] of certain alkene]]s. Commercially important polymers prepared using persulfates include [[styrene-butadiene rubber]]

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  • | year = 2007 | publisher = Wiley-VCH | location = Weinheim | doi = 10.1002/14356007.a13_443.pub2 }}</ref><ref>Römpp CD 2006, Georg Thieme Verlag 2006</ref>

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  • heterocycles are often prepared via condensation of 1,4-[[diketone]]s or 4-ketoacids and hydrazine]].<ref>M. Tišler, B. Stanovnik "Pyridazines" Advances in Heterocyclic Chemistry, Volume 9, 1968,

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periodic table[edit]

Please look at Wikipedia_talk:WikiProject_Elements#element infobox and comment if you if you wish.Petergans (talk) 16:42, 6 January 2014 (UTC)

Acetylene edits[edit]

Thank you for looking over my work once again. I will take your critiques to heart and make some appropriate changes. I agree about my illustration, it is a butt-ugly eyesore. I just thought I would draw it because the whole article set a precedence for pictures (i.e. I didn't want my submission be the only one to break the format). Anyways... I first learned of this from Ullmann's too but the coverage was a mere paragraph. The Walter Reppe 1969 source source says iron pentacarbonyl can be used as reagent when no free carbon monoxide is available to recharge the catalyst. The equation yielding iron(II) carbonate is taken verbatim from the 1969 paper. For chemists without a lab fitted with special hazard insurance (i.e. being OK'd to work with carbon monoxide), I thought small-time experimenters ought to know they can work with a relatively safe solid reagent rather than a highly poisonous gas.

As a side note on the topic of the iron pentacarbonyl usage, the 1969 source says the reaction between methylacetylene and dimethylacetylene is highly selective (regardless of stichometry) favoring 1,2,4-trimethylhydroquinone, a precursor for the total synthesis of Vitamin E. It also says that higher alkyl groups work as well for this method. Looks to me that this sort of reaction could have industrial applications (considering aromatic substitution is a pain in the ass). The author also explains the reason for this type of synthesis "going out of style" is because petroleum's rise to dominance over the prior calcium carbide industry (and acetylene's cheaper petroleum replacement ethylene). We all know that is a problem considering that we, as a species, are rapidly depleting our oil reserves. Definitely an opportunity to invent new, cheap, "future proof" syntheses of substituted aromatics...

As for topic reccomendations, besides the other occasional curiosities, I am interested in sourcing chemical reagents from renewable resources (i.e. practical yet unconventional total syntheses of reagents). It's fun to think (mostly waste time) over. If you have something weird for me in a secondary source please shoot away, I will give it a look. --ThunderSkunk (talk) 21:23, 7 January 2014 (UTC)

Well, I learned something about the hydroquinone synthesis, thanks. I thought that you blew it with ferrous carbonate and had intended to write Fe(CO)3. There is a huge amount of stuff in the Reppe area, but the main apps are hydrocarbonylation and hydroesterification of alkenes and alkynes.
The main challenge is notability, that is the reason that Wiki policy places so much emphasis of WP:SECONDARY (books and reviews). In this spirit I recommend a new review on acetylene chemistry doi:10.1021/cr400357r. Even if you do not have a subscription, you can view the articles outline.
Re your comment about the depletion of our petrochemical reserves. My understanding also is that cheap petroleum destroyed the coal-based chemical industry. Thank god though! Calcium carbide based chemistry is filthy and is probably only practiced in PRC and other places that tolerate pollution associated with making that crud. Petrochemicals are here for a long time, esp in view of cheap natural gas. Cheers,--Smokefoot (talk) 01:37, 8 January 2014 (UTC)

File:Al2Et6wedge.png[edit]

Hi Smokefoot. The H3C on top should rather be CH3 IMHO as the bond it straight upwards. It is also inconsistent with the CH3 at the bottom and the two ethyl groups on the left hand side. --Leyo 01:34, 13 January 2014 (UTC)

Drats. I thought that maybe you and DMacks would be happy! Well, at least the drawing is better than before. I will eventually redraw this again! Its been a while. Thanks, --Smokefoot (talk) 02:02, 13 January 2014 (UTC)

Boron nitrate[edit]

This looks rather odd. The "references" seem to be to boron nitride, the usual spelling mistake. The unreferenced preparation is tribromide plus nitric acid. All seems like a mistake to me. If you agree can we get it deleted?Axiosaurus (talk) 13:30, 27 January 2014 (UTC)

Well that is an odd one. As we know, all sorts of articles get entered and the dubious ones have weak refs. I guess someone must have made the nitrate ester of boric acid, but I had not heard of it. Will look around as the opportunity arises. --Smokefoot (talk) 16:02, 27 January 2014 (UTC)
Here is a reference that says it does not exist: http://www.geothermal-energy.org/pdf/IGAstandard/WGC/2005/0207.pdf but of course there could be a later one that says it does. But this references says it exists below -78°C. http://link.springer.com/article/10.1007/BF00854900 Graeme Bartlett (talk) 06:13, 1 February 2014 (UTC)

Reference Errors on 30 January[edit]

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"Cut-and-paste move"[edit]

Information icon Hi, and thank you for your contributions to Wikipedia. It appears that you tried to give Diimine a different title by copying its content and pasting either the same content, or an edited version of it, into another page with a different name. This is known as a "cut-and-paste move", and it is undesirable because it splits the page history, which is legally required for attribution. Instead, the software used by Wikipedia has a feature that allows pages to be moved to a new title together with their edit history.

In most cases, once your account is four days old and has ten edits, you should be able to move an article yourself using the "Move" tab at the top of the page. This both preserves the page history intact and automatically creates a redirect from the old title to the new. If you cannot perform a particular page move yourself this way (e.g. because a page already exists at the target title), please follow the instructions at requested moves to have it moved by someone else. Also, if there are any other pages that you moved by copying and pasting, even if it was a long time ago, please list them at Wikipedia:Cut-and-paste-move repair holding pen. Thank you. Christian75 (talk) 16:30, 31 January 2014 (UTC)

Thanks for the reminder. Although I might err in some cases, I usually follow official protocol. It would be nice to have the authority to switch the target title to an existing redirect without needing to ask for an administrator, but I get lots of help. It looks like the move that I wanted was implemented by fellow editor Edgar181. I need to go back and tidy up the redirects. Cheers, --Smokefoot (talk) 20:18, 31 January 2014 (UTC)

February 2014[edit]

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  • Hexafluoropropylene oxide]] is one of the simplest members of this class of compounds. [[Perfluoro(methyl vinyl ether]] and perfluoro(propyl vinyl ether are used as a co[[monomer]]s with tetrafluoroethylene.

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  • * [[tolidine|''o''-tolidine]] (2,2'-dimethyl-4,4’-benzidine

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  • the chlorides of sodium ([[halite]] or NaCl), potassium ([[sylvite]] or KCl), and magnesium ([[bischofite]], hydrated MgCl<sub>2</sub>. Called [[serum chloride]], the concentration of

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Perfluoroalkoxy alkane[edit]

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Tricresyl phosphate[edit]

I agree that in general primary literature should not be cited. But the ref. list already contains several others, and the paper I added extends the value of the article. So where is the consistency? Ankababel (talk) 12:29, 9 February 2014 (UTC)

I guess the article should be cleaned up, that would be the way to go rather than adding to the problem. There also is the appearance of COI between the editor who started an article on a journal edited by Ramsden and citing an obscure article by the same person in the same journal. Thanks for the note.--Smokefoot (talk) 13:29, 9 February 2014 (UTC)

Reply[edit]

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Fluoride[edit]

I saw your edit for Fluoride: https://en.wikipedia.org/w/index.php?title=Fluoride&oldid=596071903 I could see why you removed my newer sections as I mistooke that I was posting on the ion form of fluorine. I wanted to ask a few questions though: you removed the secion: "===Inorganic chemicals=== Fluorides are pervasive in modern technology. Hydrofluoric acid is the fluoride synthesized on the largest scale. It is produced by treating fluoride minerals with sulfuric acid. Hydrofluoric acid and its anhydrous form hydrogen fluoride are used in the production of fluorocarbons and aluminium fluorides. Hydrofluoric acid has a variety of specialized applications, including its ability to dissolve glass. See this book: Aigueperse, Jean; Mollard, Paul; Devilliers, Didier; Chemla, Marius; Faron, Robert; Romano, Renée; Cuer, Jean Pierre (2005), "Fluorine Compounds, Inorganic", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, p. 307, doi:10.1002/14356007.a11_307 

Mined fluorite (calcium fluoride) is a commodity chemical used in steel-making. Cryolite, Na3AlF6, is the next highest fluoride salt in industry. It is used in aluminium smelting. Formerly, it was mined, but now it is derived from hydrogen fluoride. Various other fluoride salts are used as fluxes or for the preparation of other fluorine compounds, including covalently bonded fluorochemicals." I didn't create this section but it seems to stay on subject for fluoride, I thought it should stay and I'm new to editing on wiki but I remember reading I should ask the editor if possible before reverting parts of their edits.

Also, for one of the citations you removed info, from: "<ref>{{vcite article |url=http://www.who.int/water_sanitation_health/dwq/chemicals/en/fluoride.pdf |format=PDF |year=2004 |title=Fluoride in drinking-water |author=World Health Organization}}</ref>" to: "<ref>http://www.who.int/water_sanitation_health/dwq/chemicals/en/fluoride.pdf</ref>" I've been including title and such from my citations, are you not supposed to? I want to make sure I'm not missing something. Thank you for your help.

Thanks for the note. I hope that you will have a positive experience. The nature of your impact will improve by (i) communicating with established editors and (ii) making small changes initially.
In any case, the fluoride article is on F- and related salts. At least that is the direction that the article has taken. I did not check to see if the chloride, bromide, halide etc articles are similar. You quickly can realize that there is a lot of opportunity for disciplined writing/content.
One issue that I often contend with is that infrequent editors fail to appreciate the huge prosaic applications. Instead, we get a lot of editors who want to mention their hobby (e.g. aquariums, stain removal, grandma's ant poison) or their college essay/publication as being something really important, when in fact they are negligible and obscure the big picture. Hence the need to focus fluoride on its role in aluminium and steelmaking, which really dominate. On the other hand, the use of fluoride in dental care is highly impactful, but consumes tiny fraction of the world's fluoride supply.
About the link "<ref>http://www.who.int/water_sanitation_health/dwq/chemicals/en/fluoride.pdf</ref>" You are welcome to revise if you think that I messed up. My recollection is that the link was non-functional (they call this link-rot around here) so I tweaked it.
And the RSC links and WebElements links that I am disinclined toward. These websites do not seem (to me) to be particularly authoritative. They probably/possibly borrow content from Wikipedia or chemical catalogues. I view them as quasi-adverts for some organization, such as the RSC.
I hope that this extended answer is helpful. Feel free to ask more or just go edit. Cheers, --Smokefoot (talk) 18:05, 19 February 2014 (UTC)

Thank you for the feed back, and clarification. I'll double check the link for what I was thinking but it makes more sense now. As for RSC it seem informative. I've listen to many of their podcasts and for the elements podcasts they are each produced by different professions. They mention a lot of the same information but that leads me into the other point you mentioned, about the Inorganic section. As a reader and someone that has mainly used Wikipedia for school, it seems relavant to me to include as much of the uses for a compound or an element as with fluoride isn't steelmaking or aluminium or for dental care in the big picture. The reason I even started looking it up was to look at alternative uses, but it was a little confusing the overlap between fluoride and fluorine that and the names being similar didn't help, and I made a silly mistake on my part. The inorganic section seems very relavant as I was most intrested in the inorganic properties, which does get into steel making and such, but there are so many other research sections. How do you think it would work best to include the rich diversity of an element such as F, but not include filler? I ask, only because I don't have a good answer myself. That said, maybe put the steel and aluminum section under inorganic chemistry and just have the uses divided by class of chemistry? Thank you again, --HardKhora (talk) 15:20, 19 February 2014 (Central Time)

Butoxyethanol[edit]

Hi Smokefoot! Thanks for all your help and edits with the 2-butoxyethanol page. We will try to make our sources more international and we will look into other sources. Blairwal (talk) 20:05, 19 February 2014 (UTC)

Perchlorate Suggestion[edit]

Hi, thank you so much for your help and suggestions. However, I came across some questions.
1) Be sure to emphasize secondary sources, i.e. reviews and books. See WP:SECONDARY. Absolutely required for biomedical citations per WP:MEDRS. -- How do I emphasize secondary source on bibliography?

You should mainly cite secondary sources. Articles that say they are reviews. Naive editors often like to cite fairly narrow journal articles but you dont know enough to do that well (no offense). Professors and a handful of experts are really able to cite primary literature well.

2) If you find you are using the word "recently", don't. We are not interested in news per WP:NOTNEWS. -- I haven't used recently but all I said was "it is currently a subject of legal action". Should I not use currently either?

If something is "currently… anything" then leave it out. Wikipedia is not a blog. Your content is frozen in time largely. So then two years from now someone reads your content and sees that "it is currently a subject of legal action" which is obsolete because currently was very yesterday.

3) The article is international, so do not assume exclusively US perspective. Far more readers live outside of US than inside. An essay on US regulations is inappropriate. -- I just gave what US is doing as an example. Should I just remove a discussion on US government?

then make sure that you indicate a US perspective. The EPA and FDA are the U.S. EPA and the U.S. FDA. It is a tiring to read the content from US students who are oblivious of the fact that they are a minority of readers.

4) The article is about a chemical species, not its environmental impact per se. So be balanced per WP:UNDUE. -- For part of the project, we are researching on how these chemicals are affecting humans and environment. The article already seems to have health issues involved. Would including more health issues and environment be a problem?

Just be mindful that there is a ton of (often mediocre or redundant) literature on tox and environmental stuff. So be careful. Remind your instructor that length does not correlate with excellence. We do not want the MSDS reiterated. See Wikipedia:Manual of Style/Chemistry#Safety.

Thank you Kohw 23:52, 21 February 2014 (UTC) — Preceding unsigned comment added by Kohw (talkcontribs)

Dear Kohw: First of all, thanks for the note. Second, be aware that I have zero authority here and my exhortations are only that (hot air). In the end, editors do what they want and so long as the content is moderately factual, it will largely stand. Some comments inserted above. Good luck and dont worry about me, there's not a lot that I can do. --Smokefoot (talk) 05:44, 22 February 2014 (UTC)

re: You seem to be spamming NASA[edit]

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re: Tripropylene is wrong?[edit]

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Your deletion[edit]

Wait for what? If you want to wait forever, that's your business. That was an authoritative source.--Wyn.junior (talk) 04:09, 26 February 2014 (UTC)

Out of line[edit]

You are out of line. The paper in question is published on the World Health Organization site, and is CLEARLY a secondary source, if you had bothered to examine it, as evidenced by the numerous other primary and secondary sources at the bottom of the page. I would encourage you to read the information you posted regardless, as nowhere does it bar even primary sources, stating that they should be backed up by secondary sources whenever possible if making "an interpretation", which I was certainly not doing! It is common and accepted practice to cite the same article more than once on a Wiki page. And FTR, I am not at all affiliated with any of the publishers,researchers, or authors in question! The information you wantonly deleted was cited in multiple sources, is factually accurate, and widely accepted. You seem to have a minor fixation on the issues of "sourcing" and COI. I encourage you to rethink your actions in the future to avoid conflict with your fellow editors.Jbtvt (talk) 14:38, 27 February 2014 (UTC)

Well I dont completely agree, adding many references to a single research group is highly unusual. Judging from the number of publications on lead poisoning or chelation, one can appreciate the difficulty in selecting references. Self-citation is a problem in Wikipedia that conveys distorted information, hence my concerns. In any case, thanks for being careful and I hope that I am indeed in the wrong. --Smokefoot (talk) 18:18, 27 February 2014 (UTC)

March 2014[edit]

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  • resonance values for the carbido carbons vary widely, but range from δ211-406.<ref name=Heijl2002>{{cite journal|last=Hejl|first=Andrew|coauthors=Trnka, Day, Grubbs|journal=Chem. Commun.|year=2002|
  • ==Other reading (specialized==

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  • colourless, and soluble in nonpolar organic solvents. An example dimethylcarbamoyl chloride (m.p. -90 °C and b.p. 93 °C. They are used to prepare a number of pesticides, e.g. [[Carbofuran]]

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  • '' (abbreviated IBDU) is an [[organic compound]] with the formula (CH<sub>3</sub>)<sub>2</sub>CHCH{NHC(O)NH<sub>2</sub>|<sub>2</sub>. It is a derivative of urea (OC(NH<sub>2</sub>)<sub>2</sub>),

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  • Peter "Spectroscopic identification of dihydroxycarbene" Angewandte Chemie, International Edition (2008, volume 47, 7071-7074. {{DOI|10.1002/anie.200802105}} </ref> Many related carbenes are known,

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2-Butoxyethanol[edit]

Hi, I saw your message on my Talk page and just wanted to thank you for the help you've provided for my work on 2-Butoxyethanol. My contribution to the article is for a class on environmental disruptors and I'm pretty new to Wikipedia. What I was contributing today was on 2-Butoxyethanol's environmental effects. I was also looking to provide some information on how it moves through the environment. I don't know if that helps you to understand the intentions behind my contribution, but if you need more help I could try to provide it. Custodim (talk) 01:09, 13 March 2014 (UTC)

It just seems that what you are trying to do requires a lot of expertise in biosynthetic and biodegradation pathways and access to high level sources, not just websites. So I would try to convince your teacher to get involved (probably over their head too, I would guess) or make the topic a little easier. Also, Wikipedia is an encyclopedia for rather general knowledge, not a catalogue of articles and websites. I hope that my advice does not seem harsh, but it seems that your assignment is almost too high and too vague. --Smokefoot (talk) 17:48, 13 March 2014 (UTC)

April 2014[edit]

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  • The compound is prepared by oxidation of cobalt(II) salts in the presence of potassium nitrite]]:<ref>O. Glemser "Sodium Hexanitritocobaltate(III)" Handbook of Preparative Inorganic Chemistry,

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Formic Acid[edit]

I have no commercial or other interest in Meda. They are simply (to my knowledge) the only manufacturer or distributor of formic acid for medical use. DES (talk) 14:11, 28 April 2014 (UTC)

May 2014[edit]

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  • [[Shvo catalyst|Shvo's catalyst]] ({[Ph<sub>4</sub>(η<sup>5</sup>-C<sub>4</sub>CO)]<sub>2</sub>H]}Ru<sub>2</sub>(CO)<sub>4</sub>(μ-H)) is also coordinatively saturated, but features reactive OH
  • 5</sub> and Fe<sub>2</sub>(CO)<sub>9</sub> are not very useful. The pentacarbonyl de[carbonylate]]s readily:

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  • | MeltingPt=18 °C(

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  • by the [[Arndt–Eistert reaction]], subsequent cyclization affords [[2-Tetralone|2-tetralone]],] derivatives.<ref name=Korneev/>

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  • has the [[calcium fluoride|fluorite]] structure, with tetrahedral four-coordinate hydride ligand]]s linking eight-coordinate Ti(II) centres.<ref name="Fukai">{{cite book |last=Fukai |first=Y |year=

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  • usually [[lipid]]s. [[Sudan II]], [[Sudan III]], [[Sudan IV]], [[Oil Red O]], and [[Sudan Black B]]) are important members of this class of chemical compounds (see images below).

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  • derivatives involving Co and Ni. Often derived from substituted derivatives of cyclopentadienide]], metallocenes of many elements have been prepared.<ref>Paul J. Chirik "Group 4 Transition Metal

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In re your comments at my Talk page[edit]

Smokefoot writes: Just a couple of comments/suggestions. Rather than critiquing - edit! That is what we do here. It takes less effort to consult a monograph or text on conformational analysis or VSEPR and repair something amiss vs writing "nearly all of the article is unverifiable, and parts are inaccurate or indecipherable, and so therefore are unreliable as encyclopedic content.". Start by editing in dribs and drabs. Target the worst parts of offending articles. A lot of this stuff is written by non-experts, so there is no problem with experts apparently like yourself just rewriting/deleting a section or two and then waiting to see how the revision is received. Typically deafening silence. The chemically fluent editors are helpful but tend to mildly avoid each other, not out of antisocial tendencies but because our interests diverge. FYI, IMHO the greatest long range challenge in Wikichem is WP:UNDUE, which arises from WP:COI and non-observance of WP:SECONDARY. Happy editing, --Smokefoot (talk) 23:40, 30 May 2014 (UTC)

Au contraire, many types of activities are occurring here, and some editors do no original content generation, and are quite content (and well regarded for their "contributions"). In re: "It takes less effort…"

I dont know of any "effective" contributor who just critiques, but maybe that is your niche. Wikipedia takes all types.

Again, to the contrary, one of the problems of this organization is the very low view that is taken of adequately understanding and crafting and sourcing content before posting—in large part, because just typing, and later proof-texting is so easy, relative to true, solid content generation.

well, a lot of early Wiki-chem was written by authors winging it. But that material is slowly being revised into more ground content. For example, there are not many compositions of matter described here in a misleading way. The more problematic articles are on concepts.

No, to create de novo or to fix to comparable quality of a de novo creation—these are truly much harder than just calling attention to shortcomings. (This could have been your persuasive argument, that I have taken too easy of a tack.) So I do 70-80% of the former (de novo content generation), and 20-30% of the latter (calling attention, and there, it is usually a result of reviewing links outside of the article I am generating). So I am quite comfortable, philosophically and practically with this. (Professors are paid for critical thinking and discourse. As for impact, Martin Luther did not personally reform Catholicism from within, but there is no gainsaying his impact on the history of that institution, achieved via calling attention to matters needing to change—clearly, and firmly.)

Well that is a possible accusation: critiquers are to some extent taking the easy road (at the risk of alientation from appearance of pretentiousness or effeteness). An intermediate path exists, which involves revising the really awful stuff and adding attribution to a solid text or review.
BTW, It can be a huge effort to revise an article on, say, cyclohexane conformation. Before undertaking such a project you need to assess if Cyclohexane conformation is the most effective or appropriate article for the topic. All sorts of ill-thought out overlapping topics have often been created on very similar topics. It is this level of analysis that really is taxing. Often the solution is to merge related articles, which I sometimes advocate, thinking that a few good articles are better than a lot of bad ones. I have however become convinced that what makes Wikipedia special is its accommodation all kinds of specialized stuff.

Otherwise, I am quite comfortable with my approach to offering accolades for good content creation, editing and administration (and those doing it), as well as in challenging unfit material, and interacting with others (non-expert and expert), etc. Moreover, I have been awarded for calling attention to major thrusts of editing before the actual editing is done. This strategy has been, relatively speaking, so successful that I always post a talk section before doing any major edit. (On the other hand, the more common, opposite strategy, to edit boldly and wait for reversion, has led to reversion wars—once for taking out unreferenced material, and once for not taking it out—so you will forgive if I kindly assent to "agree to disagree" on this matter.

Well, there you go. Perhaps your new reviewer style is the way to go. The question is who better than you will address the problems you raise?
Some editors focus on really specialized academic stuff vs contextualizing (or they dont know any context). Often this problem comes from COI. Academics - high level and grad students - come to Wikipedia to highlight their papers. More difficult to control are extremely specialized articles created, probably, for some COI-driven process. These editors almost never contribute more broadly. They are here to showcase their sub-subfield.

But if you are another thoughtful subject matter expert, I am sure we will enjoy working together toward high quality, secondary-referenced scientific content, side by side (even though I am non-wikipedian in my approach) Cheers. Le Prof Leprof 7272 (talk) 00:17, 31 May 2014 (UTC)

Thanks for you for the nice message and best wishes for your work here. For me, editing here is weird sort of a relaxation mechanism, so I am sort of a loner with my own complicated agenda. --Smokefoot (talk) 02:52, 31 May 2014 (UTC)
Kudos, also. It's good you know what drives you—knowing your desired destination make's it all the more likely you'll arrive. I've been in the background in chem for some time, and am only now raising my head for a breath, and then only briefly... but I am sure we will cross paths again, and productively. Cheers. Le Prof Leprof 7272 (talk) 00:05, 1 June 2014 (UTC)

TY for attention at NP[edit]

If you know other natural products guys, please, feel free and direct them to the discussion. Cheers. Le Prof Leprof 7272 (talk) 18:17, 2 June 2014 (UTC)

Not sure if there are natural products people per se, but out most active editors is User:Edgar181, He is a med-chemist trained in organic. Another med chem person is user:~K, who has been inactive but possibly checking his favorites. He started many articles on named reactions. User:DMacks is probably an organic chemist too. --Smokefoot (talk) 00:33, 3 June 2014 (UTC)

June 2014[edit]

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  • For example, treatment with [[sulfuric acid]] gives the bisulfate [C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>NH<sub>2</sub>]<sup>+</sup>[HSO<sub>4</sub>]<sup>-</sup> as a white or yellowish powder
  • s Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH: Weinheim. {{DOI|10.1002/14356007.a02_303}}}</ref>

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  • ]'''Non-stoichiometric compounds''' are [[chemical compound]]s with an [[chemical element|elemental]]
  • hydride]] is a nonstoichiometric material of the approximate composition PdH<sub>x</sub> (0.02 < x < 0.58). This solid conducts hydrogen by virtue of the mobility of the hydrogen atoms within the

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  • | BoilingPt = sublimes > 350 °C in vacuo
  • [[File:WO2Cl2(dme).png|thumb|left|Structure of the complex WO<sub>2</sub>Cl<sub>2</sub>(dimethoxyethane.]]

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  • <ref name=Chand/> The organotin halides for adducts, e.g. Me<sub>2</sub>SnCl<sub>2</sub>([[2,2'-Bipyridine|bipyridine]].

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  • Acetylferrocene is prepared by [[acetylation]] of ferrocene, usually with acetic anhydride]]:<ref>Donahue, C. J., Donahue, E. R., "Beyond Acetylferrocene: The Synthesis and NMR Spectra of a

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  • in the ocean. At 100 °C water, the concentration of titanium in water is estimated to be <10<sup>-7</sup> M at pH 7. The composition of titanium species in aqueous solution remains unknown

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Glyoxylic acid (contd.) - no Chemical Reviews the journal[edit]

Hello Smokefoot, after reading your comments of not using primary sources, how about journal articles from Chemical Reviews ?-- Mountainninja (talk) 18:35, 11 June 2014 (UTC)

For chemists, Chem Revs is one of the best secondary sources, IMHO. Good luck with the glyoxalic acid quest. --Smokefoot (talk) 22:07, 11 June 2014 (UTC) Addendum: I have a conflict of interest in the sense that I serve Chem. Rev. in an advisory capacity. --Smokefoot (talk) 23:20, 11 June 2014 (UTC)

Re:Bulk chemicals[edit]

Thank you for your message. It is a synonym of Commodity chemicals. I have created the redirect now. --Daniele Pugliesi (talk) 18:21, 16 June 2014 (UTC)

ooookay, where is the list of "commodity chemical" defined. --Smokefoot (talk) 18:24, 16 June 2014 (UTC)
In the page Commodity chemicals. However I am looking know to find some source and it looks that there is a little confusion about these terms. Furthermore, looking this Italian page it looks like that there are two types of commodity chemicals, so now I am not sure that the terms "bulk chemicals" and "commodity chemicals" are exact synonyms: most likely "bulk chemical" is a synonym of "branded commodity chemicals". Give a couple of days to check these definitions in a reliable source; in the meantime you can put some notice in the category to advice (maybe template:WIP?) that I am checking this category. If I found some good source, I would create two similar categories for speciality chemicals and fine chemicals. --Daniele Pugliesi (talk) 18:33, 16 June 2014 (UTC)
Sounds like OR to me. --Smokefoot (talk) 18:38, 16 June 2014 (UTC)
I am going to create a page called "commercial classification of chemicals" or "industrial classification of chemicals" (see User:Daniele Pugliesi/Sandbox/2); in the case it will be too short, it can be incorporated in Chemical substance or Chemical industry. During the creation of this page/section I will check the meaning of each term in some reliable source. In the case of "bulk materials", I found this term somewhere (I don't remember where at the moment) as a synonym of "commodity", but now I am doubting that they are synonyms, so what do you suggest about the Category:Bulk chemicals? It is fine to leave it there another couple of days and in the meantime I check it, or it is better to delete it and decide after about its creation? Do you have any other suggestion/comment about the commercial classification of chemicals? --Daniele Pugliesi (talk) 19:04, 16 June 2014 (UTC)
Although with best of intentions, you may be engaged in a tricky game especially since you are starting this process before you have good sources. Yes, we realize that some compounds are made on a large scale. I recommend caution because I doubt if official definitions exist for bulk, commodity, or specialty. Related to petrochemical and petroleum products, you might want to start a category on one of those reasonably well defined labels. Good luck, --Smokefoot (talk) 19:45, 16 June 2014 (UTC)

I am translating it:Classificazione commerciale dei prodotti chimici, where there are enough sources about the definition of "commodity chemicals" and a clear (I think) explanation of its meaning. I am going to create also a table with the worldwide production of these chemicals: in fact one peculiarity of commodity chemicals is their high production. --Daniele Pugliesi (talk) 16:00, 29 June 2014 (UTC)

In it.wikipedia I never had to ask for categorization. For this reason I didn't look for consensus. I used the list in Commodity chemicals, where there is the definition too. I will put the sources in the next days. Sorry for my English and my boldness. --Daniele Pugliesi (talk) 17:04, 29 June 2014 (UTC)
Thanks for the response. I look forward to seeing a good definition. In terms of boldness, it is usually a good idea to be bold, but when one is challenged by experienced editor and when the edit has broad impact. Seeking consensus seems prudent, healthy, and collegial. --Smokefoot (talk) 17:24, 29 June 2014 (UTC)

Thanks for visit to NP article and[edit]

...wanted to call your attention to my shading of your entries. This is being done, so new editors comments are not lost in the sea of counter-discourse between Boghog and I. Doing so makes the new comments and questions easier to find, and easier to refer to. Since we get along fine, I am going to assume it is alright, but just ping me / say here if it is not OK. Le Prof Leprof 7272 (talk) 15:55, 19 June 2014 (UTC)

A last short needed look[edit]

Please see possible "closing arguments" here, [1], and consider a final persuasive comment. Cheers. Le Prof Leprof 7272 (talk)

Water fluoridation controversy edits[edit]

Hello- I made several changes to the water fluoridation controversy page, which were reverted with a suggestion to post an explanation of all edits on the talk page for discussion. I did so, but there have been no comments, so I'm not sure where to go from there since I've never dealt with reverted edits before. I don't know if there is an etiquette that requires a certain amount of time before I should reinstate the changes, or if someone else would do so. User:Rebecca_hare — Preceding undated comment added 17:34, 23 June 2014 (UTC)

Rebecca: the etiquette, to the extent it is defined, is for me to act on you cooperative gesture in a timely manner, which I failed to do. I will revert my revert. Thanks and good luck. --Smokefoot (talk) 23:14, 23 June 2014 (UTC)

filenames[edit]

Filenames should be clear and informative, and minimize ambiguity. If the filename could plausibly be used for a completely different image, it's not a good filename. DS (talk) 18:37, 26 June 2014 (UTC)

Cudennec et al - what gives?[edit]

Is there a reason that you repeatedly cite fairly specialized papers by Cudennec et al? Just curious, but I look forward to a response. --Smokefoot (talk) 16:07, 28 June 2014 (UTC)

Oh, I see you are Y. Cudennec. I encourage you to read about WP:COI. I will revert some of your edits because of this issue. --Smokefoot (talk) 19:50, 28 June 2014 (UTC)
Ok, i have suppressed my own publications list, which appears in the text, but not references of concerned papers.Maghemite (talk) 23:33, 28 June 2014 (UTC)
Thanks! We are not supposed to cite ourselves. Or do so very rarely and mainly for WP:SECONDARY. I should add that almost every academic research makes the same mistake when they start editing here. Obviously you were not trying to trick anyone. I hope that you can edit articles where you know something but do not cite yourself. --Smokefoot (talk) 23:43, 28 June 2014 (UTC)
Of course, i have mainly contributed (in french but also, a little in english ) about thermodynamic, in citing Peter.W.Atkins. Sincerely Yours Maghemite (talk) 09:46, 29 June 2014 (UTC)

Noyori Ru-BINAP[edit]

Thanks for your comments. I agree the image is too large. I can fix that. Can you suggest how to correct the steps of the mechanism? My goal was to exactly replicate the mechanism already on the page, did I miscopy it, or is the original mechanism also incorrect? --Azmanam (talk) 19:57, 3 July 2014 (UTC)azmanam

Well the main thing is that it is nice that you want to contributie. One suggestion if you are a new editor is to work on smaller scale projects than some grand mechanism. We need articles on many useful ligands for example. Lots of articles on complex heterocycles lack citations. Try to stick to secondary sources (see WP:SECONDARY) like reviews. Another way to contribute is to find a good review, like in Chem Rev or Advances in ... --Smokefoot (talk) 13:07, 4 July 2014 (UTC)
Thank you for your reply. First, you did not respond to my questions. Can you point out what is incorrect in the mechanism so I may at least know for my own edification. Second, I don't appreciate the condescending implication of your comment that newbies can't make meaningful edits. I get the concept of building up credibility, but patronizingly redirecting me to 'smaller' projects feels dismissive. Don't pull rank, that's unbecoming. Let's talk chemistry and work to make WP better. --Azmanam (talk) 20:53, 7 July 2014 (UTC)
Sorry, I am not trying to be unwelcoming, but encouraging a new editor to start small is the usual advice that one follows in the lab as well as in Wikipedia editing. On technical articles, it is a good idea to go incremental. One problem with your scheme is that it invoked Ru(I). --Smokefoot (talk) 23:34, 7 July 2014 (UTC)
Thank you. And thank you for your comments on the article talk page. --Azmanam (talk) 13:11, 8 July 2014 (UTC)
Question: if you dont know enough basic organometallic chemistry to avoid these easy errors, why are you pressing to create images for the world to see? --Smokefoot (talk) 13:29, 8 July 2014 (UTC)
Fair question, friend. My goal was not to add knowledge to Wikipedia, my goal was to redraw mechanisms or schemes from WP that could look better with a little forethought into design. It started on Twitter as #ChemDrawChallenge, where we would take a sloppy or confusing ChemDraw image from a paper or from Wikipedia and redraw it with design in mind. Not change it or modify it at all, just redraw it. This image came from our third or fourth #ChemDrawChallenge and I liked it enough to replace the one on Wikipedia. Again, I had no intention of changing the mechanism, just recreating it. So while I am a Ph.D. organic chemist, and it's true I don't have the trained eye of an organometallic chemist and didn't see the basic errors, the question behind your question is how did that original mechanism last so long on the WP page if it suffers from the same basic organometallic errors?
But even that question doesn't really matter. My question is, is the original mechanism nice to look at? Could it be more clear or more appealing with a little face lift? And if it has errors, can we both fix those errors and make it more aesthetically pleasing and/or even clearer than the original? Is that structure in the original on the bottom right labeled 'Unfavored TS' clear and easy to read? I'm not necessarily saying my drawing was clearer (I hope it was, that was my goal), but the point was not to add knowledge, but to add aesthetics. I wish I had the ability to correct the errors and make it more appealing, but I did not. Let's work together to accomplish both goals. --Azmanam (talk) 19:51, 8 July 2014 (UTC)

Metal carbonyl[edit]

Hi Smokefoot, I would like to introduce a chapter about nomenclature (like here. Any comments or suggestions from your side? -- Linksfuss (talk) 12:48, 6 July 2014 (UTC)

Well you are encouraged to help out. The set of drawings has the following quirks, for me:
  • The number of bonds between C and O seems strange (But I dont know how to depict them perfectly)
  • mu-CO are typically more symmetrical than shown.
  • perhaps too much emphasis on exotic CO bonding modes? (e.g., mu-6)

Hope this helps. --Smokefoot (talk) 12:59, 6 July 2014 (UTC)

Thank you, I´ll give it a try. -- Linksfuss (talk) 13:12, 6 July 2014 (UTC)
P.S./fyi: M. M. Hirschmann: Fe-carbonyl is a key player in planetary magmas. In: Proceedings of the National Academy of Sciences. 110, 2013, S. 7967–7968, doi:10.1073/pnas.1305237110.

Photographic film edits[edit]

Hello,

It is heartening to find a proper chemist reviewing the technical accuracy of this article, and cit-starved as it is, the addition of any high-quality reference is cause enough for rejoicing, but I question whether some recent copyediting in the lead really represents progress.

To my eyes, "... creates an invisible latent image in the emulsion, which can ..." said just the same thing as "... creates an latent image in the emulsion. Although invisible to the eye, this latent image can ...", but in fewer words and perhaps a bit more clearly because of it.

My understanding of WP guidelines is that the lead is supposed to be concise and written in terms that are as non-technical and accessible to the general reader as possible, which also throws into question the wisdom of reiterating the basic concept of a "slight chemical change" as an "incipient chemical reaction", a more dauntingly technical albeit more specific description that may be counterproductive detail in this context.

:I was trying to remove jargon or explain it a little better, but you seem to have a good way of writing, so I am cool.

A link to the broader topic of photographic processing rather than to photographic developer seems more likely to be helpful to the uninitiated -- and development alone will not produce the "visible and permanent image" subsequently promised by the new wording without the fixing step that is an integral part of the former article's subject.

:I will look at photographic processing. Photographic developer seems redundant, rambling, and seems to be hankering to give advice. I might re-write it more concisely.

Finally, a beef which is not my own but which I am inclined to take to heart. Another editor has ranted with evident exasperation that the image, strictly speaking, is what the camera lens projects onto the photosensitive surface; the resulting artifact is a photograph of an image, not an image. The lens of the eye projects an image of the photograph onto the retina. Common usage rarely makes that distinction -- even collectors of vintage photographs usually call their swap meets "image shows" -- so it is certainly not mandated here, but when possible without making the wording too awkward I now incline to referring to the artifacts themselves as "photographs" rather than "images". Therefore, the former "... visible photograph" seems preferable to "... visible and permanent image, the photograph" for multiple reasons. AVarchaeologist (talk) 23:19, 6 July 2014 (UTC)

:Well that kind of thinking can drive one nuts. Not sure it serves our readers. Please let me know how or where I can help. --Smokefoot (talk) 00:23, 7 July 2014 (UTC)

July 2014[edit]

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  • dianhydride]]. Common diamine building blocks include [[4,4�-diaminodiphenyl ether]] )"DAPE"), [[1,3-Phenylenediamine|meta-phenylenediamine]] ("MDA"), and 3,3�-diaminodiphenylmethane.<ref name=

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  • :3 [H<sub>2</sub>N)<sub>2</sub>CO → [H<sub>2</sub>NC(O)NH]<sub>2</sub>CO + 2 NH<sub>3</sub>
  • :2 [H<sub>2</sub>N)<sub>2</sub>CO + COCl<sub>2</sub> → [H<sub>2</sub>NC(O)NH]<sub>2</sub>CO + 2 HCl

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  • are derivatives of urea, a straight fertilizer providing nitrogen. [[Isobutylidenediurea]] IBDU) and urea-formaldehyde slowly convert in the soil to free urea, which is rapidly uptaken by plants.

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  • (N<sub>2</sub>) by converting it to ammonia. Phosphate is required for the production of ATP]], the main energy carrier in cells, as well as certain lipids.
  • These concise formulas are shorthand for the nature of the phosphorus (phosphate) or potassium (K<sup>+</sup> sources.

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  • Its [[biosynthesis]] has been examined. It arise via the action of 2-isopropylmalate synthase]] on [[α-ketobutyrate]]. The incorporation of Nle into peptides reflects the imperfect selectivity

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Fertilizer page[edit]

Thanks for your contribution; I have been chipping away at some of the details, but I agree that major changes in structure are necessary; use of the term "organic fertilizer" also needs to be tightened up - See Talk:Fertilizer

Regarding your comments about Cracking (chemistry) on my Talk page[edit]

Hi, Smokefoot: In general, I would agree with your comments. However, as I am now almost 92 years old and also that I have not had anything to do with the subject article, I hesitate to get involved in re-writing parts of that article. Please try to get some chemist (rather than a chemical engineer) to get involved. mbeychok (talk) 17:54, 9 August 2014 (UTC)

Re: chemistry articles[edit]

I've read your comment (message?) on my page. I understand what you mean, but I was just adding some info that could not be found anywhere else and I once needed, and couldn't find on wiki. Anyway, I'll refrain from adding manual-like content (pretty much the only stuff I can add, sadly). It's better being told right at the beginning then after writing a lot. Valeg96 (talk) 12:24, 15 August 2014 (UTC)

I'm replying here because this whole talk thing seems a bit complicated (it says if I reply on my talk you won't have notifications?) and I don't have time to take a full tour of everything. What has been amended/removed, just to know? Something else other than the H3PO4 synthesis? Valeg96 (talk) 14:33, 15 August 2014 (UTC)
Yes, I amended your edit on MnO. You can always check the history of edits by clicking on the history tab at the top of your page. Or you can check up on the editing activity of anyone by clicking "User contributions" on the left side of any user page. So if you look at my contributions, about ten entries ago, I made a big edit on manganese(II) oxide. And then you can see that today, inspired by your contributions, I edited iron(II) oxide. --Smokefoot (talk) 17:30, 15 August 2014 (UTC)
I also reverted your edit on chromium trioxide. It is made from the sodium salt. The potassium salt is mainly for teaching and academic labs. --Smokefoot (talk) 17:38, 15 August 2014 (UTC)
You really think that PH3 is produced industrially from the KOH vs NaOH? Seems unusual. Recall we are discussing how things are made industrially, not how the could be made. --Smokefoot (talk) 17:53, 15 August 2014 (UTC)

August 2014[edit]

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  • 1-Aminoethanol exists in a solution of acetaldehyde and ammonia.<ref>{{March6th}}</ref> [[Alanaminol can react with [[formic acid]] to form the amino acid [[Alanine]], releasing water.

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  • "p-Tolylsulfonyldiazomethane" Org. Synth. 1977, vol. 57, 95. {{DOI|10.15227/orgsyn.057.0095}}}</ref> NOCl converts some cyclic amines to the alkenes. For example, [[aziridine]] reacts with

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Electron Configuration[edit]

I added the el. conf to the Cr(IV), and you reverted it with the comment

well intentioned edit but gets d config wrong uses old fashioned analysis vs ligand fd

Can you please explain your comment further, I am not sure if I get what you are trying to tell me. PZim (talk) 01:01, 29 August 2014 (UTC)

Hi thanks for the note and the opportunity to discuss things. Cr(IV) is d2. Your well intentioned edit also includesd atomic configuration, but in compounds (vs gas phase metal ions) atomic configuration is not typically useful because the effects of the ligand field dominate the splitting. --Smokefoot (talk) 03:50, 29 August 2014 (UTC)

PTFE - "low resistance against flowing liquid"[edit]

I have just removed (from the article about PTFE) the following paragraph:

Another major application is in fuel and hydraulic lines, due to PTFE's low resistance against flowing liquids. Colder temperatures at high altitudes cause these fluids to flow more slowly. Coating the lines's interior surfaces with low-resistance PTFE helps to compensate by allowing the liquids to move more easily.

I wrote the detailed justification at the talk page of this article: Talk:Polytetrafluoroethylene#Low resistance against flowing liquid ???. Interestingly, there was a citation attributing this false statement to Ullmann's Encyclopedia of Industrial Chemistry (doi:10.1002/14356007.a11_393) and it was you, who added this reference by this edition:http://en.wikipedia.org/w/index.php?title=Polytetrafluoroethylene&diff=prev&oldid=591314363 . The statement itself was added long time before by an anonymous user, without any citation. Could you please explain what exactly have you found in this Ullmann's Encyclopedia about "low resistance against flowing liquids"? As a PhD in physical chemistry and physics I am sure, that there must be some misunderstanding, but I do not have this book nor the access to its electronic version. Tescobar (talk) 17:24, 2 September 2014 (UTC)

Thanks for the diligence. Perhaps we should rephrase that statement. here are some quotes

"Uses [for Teflon in general]

About half of the PTFE resin that is produced is used for electrical purposes …”

... Other important uses of PTFE resin are found in fluid-conveying systems, where it is used for gaskets, molded packings and seals, piston rings, bellows, overbraided hose, and lined pipe." --Smokefoot (talk) 23:51, 2 September 2014 (UTC)

Have a look?[edit]

Methylammonium.png

Due to a number of (new in the last couple years) to this class of compounds, and some odd redirects (methylammonium chloride -> methyamine) I believe it would be worthwhile to document the following materials:

  • Methylammonium iodide
  • Methylammonium chloride
  • Methylammonium bromide

Because they're increasingly mentioned in the literature on solar cells. There's limited information out there about melting points &c, but the compounds are all "known" to pubchem, chemspider, SMILES, etc. Likewise the old literature (mostly crystallographic) is of interest to the Xray crystallographers, and the new data is interesting to the solar cell crowd. Rather than add three pages (there is no substantial mention of the fluoride) I thought a category page ala acyl halide and hydrogen halide might be worthwhile, so I took a stab at it in my sandbox:

Would you kindly have a look and see if you think it's adequate to add? Follow up on my talk page if you will. If nothing else, now there's an image file for the methylammonium ion. Riventree (talk) 23:24, 9 September 2014 (UTC)

Hi Riventree, great idea in my opinion. I bet these salts are used in all sorts of ways. It would be interesting to describe the structures with respect to hydrogen-bonding. Also whether these salts form hydrates. But that content can be added over time and eventually various editors will find some review on this area. I have also heard about various quat-PbI3-based perovskites. Here is a drawing you might want to use for the chemboxes:
Chemical structure of methylammonium cation

Cheers,--Smokefoot (talk) 02:43, 10 September 2014 (UTC)

Woot. It's up. Methylammonium halide. Feedback welcome.

  • I used the image provided by User:Smokefoot
  • I agreed with User:Materialscientist about how bad the triple-sidebar was, and got inventive.
    • Horizontal "sections" for each constituent. Not applicable for large families, but looks decent
    • Maybe it's a new style!

Riventree (talk)

September 2014[edit]

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  • carbide]] powder diluted with other refractory materials such as [[alumina]] or silicon carbide]]. Potassium [[tetrafluoroborate]] (KBF<sub>4</sub>) is used as a flux. The process converts some

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  • Rather is is generated by reaction of hydrates with [[dinitrogen pentoxide]] or of nickel carbonyl]] with [[dinitrogen tetroxide]]:<ref name=Ullmann/>

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  • | isbn = 978-0-87335-233-8 | author1 = Mining, Society for | author2 = Metallurgy, | author3 = ), Exploration (U.S | date = 2006-03-05}}</ref> A typical plant produces one to two times as much red mud as
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  • Rechargeable Batteries."Chemical Reviews 2004, volume 104, pp. 4303-418. doi|10.1021/cr030203g}}</ref>
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  • /ref> It is used heat resistant [[high explosive]]. It is slightly soluble (0.1 - 5 g/100 mL) in [[butyrolactone, [[DMF]], [[DMSO]], and [[N-methylpyrrolidone]].

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  • * alanaminol (HOCH<sub>2</sub>CH(NH<sub>2</sub>)CH<sub>3</sub>) [[alanine]])
  • * sympropaminol ([[2-Aminoisobutyric acid|[2-aminoisobutyric acid]])

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  • :(NPCl<sub>2</sub>)<sub>3</sub>]] + 2 NH<sub>4</sub>Cl → P<sub>3</sub>N<sub>5</sub> + 8 HCl
  • ] upon heating to form [Diammonium_phosphate|(NH<sub>4</sub>)<sub>2</sub>HPO<sub>4</sub>]] and [[Monoammonium_phosphate|NH<sub>4</sub>H<sub>2</sub>PO<sub>4</sub>]].

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  • has long been assumed to feature an As=As [[double bond]], akin to the N=N linkage in [azobenzene]]. However, in 2005, an extensive [[mass spectrometry|mass spectral analysis]] Salvarsan was shown

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Steudels reviews as e-books[edit]

no I wasn't aware that they were now e-books. I last consulted these at the university which is a bit of an inconvenience. Thanks for the heads up. I shall acquire them. There's no more space on my shelves for printed chemistry books. Axiosaurus (talk) 16:10, 11 October 2014 (UTC)

Heme Carbon Monoxide / Cyanide binding[edit]

You reverted my addition to the Heme article that CO and CN- bind the iron center in heme, which is responsible for carbon monoxide poisoning and cyanide poisoning. Both attach to heme ligands, but in different enzymes. CO poisoning binds more to hemoglobin and partially to cytochrome c oxidase. CN poisoning binds more to mitochondrial cytochrome c oxidase but also to hemoglobin, preventing uptake of oxygen. Both Hemoglobin and Cytochrome c oxidase rely on temporary binding of oxygen. Hemoglobin so it can carry oxygen to cells, and cytochrome c oxidase to convert oxygen into water. Hemoglobin + CO --> Carboxyhemoglobin. Hemoglobin + CN --> Cyanohemoglobin. Binding of CO or CN to a heme molecule prevents oxygen from binding. The same mechanism prevents both enzymes from functioning correctly. — Preceding unsigned comment added by Zuloo37 (talkcontribs) 22:58, 12 October 2014 (UTC)

Your enthusiasm is admirable, and you know a lot of chemistry, but it is still worth exploring your proposed edits on Talk pages before inserting them. You arent required to, of course, but it would be a good idea to give you a chance to hear different perspectives. Most of these articles already mention the affinity of heme proteins for these ligands. The lethality of cyanide is according to my understanding completely attributable to the electron transfer chain being shut down, not hemoglobin or myoglobin getting hit. Although now I see that even cyanide poisoning lacks a decent reference. Also, these kinds of assertions benefit from reference to a textbook or a review. I any case I will revert by reversions and give us both some time to get this sorted out with some nice solid refs. Hows that? --Smokefoot (talk) 02:56, 13 October 2014 (UTC)

Red-Al[edit]

I see you've also noticed the flurry of editing at Red-Al. I've not checked over the edits yet but the images now have errors (at least to my eyes). I've mensioned it on the article talk page. Any idea whats going on here? Project Osprey (talk) 14:03, 14 October 2014 (UTC)

Beats me. Possibly a homework assignment, possibly a marketer of this stuff. Following your suggestions I went back to the article. I dont use it but my colleagues call it Vitride. You are welcome do dive in. --Smokefoot (talk) 17:37, 14 October 2014 (UTC)
I'd suspect a school project. Everyone I know calls it "Red-Al", some name-reaction/common-reagent books call it SMEAH. Using the systematic/chemical name is reasonable for the article itself. TONE/NPOV is surprisingly good if it were a corp promoter:) But as often for merger of a huge pile of new-content and changes, they were poorly integrated. I hacked on it a bit. DMacks (talk) 18:42, 14 October 2014 (UTC)
On looking further, possibly promoter, and the content isn't all that good:( DMacks (talk) 07:40, 15 October 2014 (UTC)
On-wiki evidence of it being some school thing via cs.wp. DMacks (talk) 18:09, 15 October 2014 (UTC)

Copper(III) oxide[edit]

You can't restore a prod once someone other than the creator of the article has removed it. I see no other admin has been willing to do the deletion either. You will need to take it to AfD. I restored the fuller version with the link to the ruWP. I'm not an expert in this subject, but there do appear to be refs mentioning it. DGG ( talk ) 21:07, 2 November 2014 (UTC)

I am sort of an expert on the subject and the Russian Construction manual is not a credible citation. But I will take a look again and try to prune silly stuff. Thanks for the help and note. --Smokefoot (talk) 22:21, 2 November 2014 (UTC)

Reference Errors on 19 November[edit]

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C-H activation page[edit]

Thanks for the suggestions to the page, but I disagree with some of them. Including numbers in figures (not artwork) is found in scientific journals, and is easier to understand. This page is for the public in the end. The figures I have added follow those from journals and are cited. There is active research for developing new methods for C-H activation as well as using available methods, so I'm not being "gullible". The slides are cited, what's the issue with that? You can find them on google. I'm still fixing up the page, adding explanations, more examples and am reworking the page entirely. Thanks, Sarmalkow (talk) 05:42, 3 December 2014 (UTC)

Two points. First, thanks for the message and second, Wikipedia has guidelines, which you are encourage to learn a little about.

First of all, yYou dont own the article. See Wikipedia:Ownership of articles. We all edit each others work all the time. Routine. And experience shows that students homework assignments could almost alway be improved - do you agree? Some specifics: The term "recent" becomes stale in a year or two in the encyclopedia, no one is using Periana catalysis for methane activation. Ever. Why refer to him with a title Prof? etc. We prefer to avoid words in artwork. You are not writing for the US only, what if other language Wikis want to use the art? they are stuck with the English in many schemes. Yes, journals do that but they also copyright their artwork, Wikipedia does the reverse, we share our artwork. For many Wiki readers, English is not their language of choice. See this Wikipedia:Manual of Style/Chemistry#Reactions.--Smokefoot (talk) 15:00, 3 December 2014 (UTC)

I know that WP is public and anyone can edit any article. I don't need a lecture on that. How is a student homework assignment relevant? "Recent" is relative. Periana catalysis was in the article previously; I just moved it into a different section. Even if it isn't used anymore, it still provides context. The prof title was in the article previously. What words in the FIGURE (it's not artwork)? Guided and Innate? It lends to making the content more digestible, or that's what I understand (look at the article, they do it). I'm not writing for just those that read English, yes, but two or three words in a figure doesn't ruin it. You can say the same about color; color in a figure isn't helpful for those who are color-blind. WP is for the public, including those that aren't familiar with the subject. Hence, removing introductory information to contextualize an idea isn't conducive toward achieving that goal. Oh, and removing the figure from reaction conditions...that figure has been on the page forever. I'm still adding to the page. Also, if you're going to talk to users, take the time to check your spelling and grammar.Sarmalkow (talk) 19:05, 3 December 2014 (UTC)

I'll address one point: use of numbers to identify structures in an image. The fundamental problem is that it ties the image to the article at the point it was created. The image becomes less usable in other contexts. And the article itself becomes less editable because if the images get shuffled around the numbers get out of sequence. And if new images are created, they need to sync with the same numbers previously used for each compound. For example, there's no need to put any number in "File:Steric Effects Figure 1.png" because it's the only structure there and there is no other use of it elsewhere in the article--one can just say "the image above".
Okay, I find I'm headed into some other points...The experimental results (specific catalysts and their product ratios) can similarly be removed and simply described in the text (since it really is just text anyway). Or simply omitted altogether (Wikipedia focuses on secondary references, so seeing this specific set of primary data is possibly too detailed). Even the filenames such as that one's emphasize how tied to "the current writing of the current article" it is rather than being a sharable image on a centralized server for an article that will evolve over time. DMacks (talk) 19:37, 3 December 2014 (UTC)
I guess I just find figures with numbered compounds helpful. I agree with the figure containing only one structure, but disagree when multiple structures are present. And if this is an issue, why do other pages contain words and numbering in figures? i.e. Cycloisomerization, Cieplak Effect, Wittig Reaction, Horner-Wadsworth-Emmons reaction. I was simply trying to improve a page in need. Sarmalkow (talk) 03:00, 4 December 2014 (UTC)
I know that two of those articles you mention were written from scratch (including the images) within the past few days by editors who also are new to Wikipedia. It's not unusual for new editors not to know the local style guidelines and conventions. Some of those are even worse in that the "Figure #" is part of the image itself, making the article highly resistant to any edit that would insert, remove, or re-order the images. I vaguely remember a discussion years ago generally disfavoring "Figure 1" and the like (not specific to chemistry articles) but I can't find it in the Manual of Style at the moment. DMacks (talk) 03:17, 4 December 2014 (UTC)
Sarmalkow, thanks for engaging us. This time of year, and again in the spring, Wiki-chem gets a burst of homework assignments, like yours. These students are trying to do the right thing but how could they possibly know the guidelines? Unfortunately, instructors are rarely involved and also do not know Wiki-guidelines. U.S. students especially seem rarely mindful that Wikipedia is highly international, with the consequence that artwork can be shared over many languages, hence our encouragement that you edit your ChemDraws. Another characteristic of homeworky projects is that rather than making incremental, integrated edits, which is the way Wikipedia tends to grow well, students drop a large and often self-standing essay that does not integrate well (like your compound numbers) into our exsiting content. Understandably: students are looking for a grade and they are rarely going to come back to Wikipedia and "clean up after themselves." So now you know some perspectives, we wish other students did the same, but you got picked on and your classmates did not. Let us know if we can help. One way you can help is to pass on this advice to your instructor! --Smokefoot (talk) 03:38, 4 December 2014 (UTC)
Shouldn't we be grateful that information is added? It helps everyone out. I think the approach to familiarizing new editors is just a little harsh. New editors are just trying to help, like seasoned editors. Thanks for the insight. Sarmalkow (talk) 04:37, 4 December 2014 (UTC)
Yes, we are being a little harsh, or actually frank. Wikipedia is the recipient for a lot of homework, all well intentioned, maybe slightly naive.... So what we are trying to say is that with a little tweaking, your (and your fellow students') contributions could much more helpful. But point made about rule, harshness, my bad spelling, etc. Good luck. --Smokefoot (talk) 05:01, 4 December 2014 (UTC)
I also agree with the "thanks for contributing" and the value added by even good content that is not up to great style. And I also echo the need to get feedback back to the instructors about how they can better work with Wikipedia and help their students understand/become more quickly accustomed to the nature of Wikipedia. DMacks (talk) 08:48, 4 December 2014 (UTC)

disingenious[edit]

Per this, and because of the disingenious replies you put there today, I state that you are not welcome on my userspace any more. Don't edit there. -DePiep (talk) 20:19, 7 December 2014 (UTC)

You might be reading a little more into my queries, but whatever. We all have bad days. I am not sure one can or would want to ban another editor from leaving a message, but one could always delete the message. --Smokefoot (talk) 20:39, 7 December 2014 (UTC)
q.e.d. -DePiep (talk) 20:43, 7 December 2014 (UTC)

removal of See Also links on EDTA page[edit]

Hi, I understand you may not be familiar with the preservatives used in ocular pharmaceuticals, but it would have been polite for you to follow up with me (or any online source) to educate yourself first, rather than just reverting my edit. WitheredLimb (talk) 03:02, 9 December 2014 (UTC)

Oh thanks for the note and sorry to have behaved impolitely. I saw that someone else deleted your see also link. For the EDTA article, if we made a see also link to every app of this common chemical, it seems that the list would be quite long, dont you think? --Smokefoot (talk) 04:51, 9 December 2014 (UTC)
They weren't apps you deleted, they were alternate preservatives to EDTA used in ocular pharm. Increasingly EDTA is used instead of BAC, so I have added EDTA to BAC page (as well as other 3rd gen and 1st gen preservatives). For completeness they were also added to EDTA page. Don't see an issue with listing alternatives - there actually aren't that many. Am getting used to my edits being reverted. Think I might be in the wrong place here. — Preceding unsigned comment added by WitheredLimb (talkcontribs) 05:06, 9 December 2014 (UTC)
You are definitely not in the wrong place. And I can be an aggressive editor. So the collision of your relative inexperience with my ways is surely frustrating. You handled the situation perfectly: with a note to the deleter. The other angle you can take is, if you think my action was ill-advised, is revert what I did with some comment (explanatory or semi-snark).
I avoid giving advice because I am no guru, but here goes. We all get absorbed in our specialties and are keen to share our hard-won insights. The problem is that our pet knowledge (mine too) is often rather specialized. But then our edits run the risk of violating this guideline WP:INDISCRIMINATE. --Smokefoot (talk) 06:10, 9 December 2014 (UTC)

KClO4[edit]

Hi.

Just a quick note to let you know I saw your comments and have been clued.

As my father (rest his benighted soul) always said: live and learn.

Roger Roger -Dot- Lee, Aviation Geek, perpetual student, amature scientist (talk) 04:21, 13 December 2014 (UTC)

I actually kinda agreed with your removal of those weird names, but have become so politically correct that I sent the message to you. Best wishes to you and your father's soul, --Smokefoot (talk) 04:59, 13 December 2014 (UTC)

Your comment at WP:ENI[edit]

Hi Smokefoot. Regarding this thread. Did you mean to say 'should not allow' rather than allow? Thanks, EdJohnston (talk) 04:19, 14 December 2014 (UTC)

December 2014[edit]

Hello, I'm BracketBot. I have automatically detected that your edit to Lead styphnate may have broken the syntax by modifying 2 "()"s and 3 "{}"s. If you have, don't worry: just edit the page again to fix it. If I misunderstood what happened, or if you have any questions, you can leave a message on my operator's talk page.

List of unpaired brackets remaining on the page:
  • :(C<sub>6</sub>N<sub>3</sub>O<sub>8</sub>}MgH<sub>2</sub>O + Pb(CH<sub>3</sub>CO<sub>2</sub>)<sub>2</sub> → (C<sub>6</sub>N<sub>3</sub>O<sub>8</sub>}PbH<sub>2</sub>O + Mg(CH<sub>3</sub>CO<sub>2</sub>)<sub>2</sub>
  • <!-- something messed up here:C<sub>6</sub>N<sub>3</sub>O<sub>8</sub>}PbH<sub>2</sub>O → Pb(CN)<sub>2</sub> + 4 CO<sub>2</sub> + 1/2 H<sub>2</sub> + H<sub>2</

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Zinc phosphide[edit]

Thanks for that. Never come across zinc phosphides before - so quite interesting- a semiconducting rodenticide no less. The coordination of Zn in Zn3P2 is approx tetrahedral, P is 6. A bit weird- the structure is sort of fluorite like but as not all T holes are filled the coordination is 6 of the vertices of a distorted cube. ZnP2 has infinite P chains- anions if you like limiting ionic structures although its a semiconductor too. The structure images we put up in wikipedia do not always do the coordination justice particularly when the coordinated atom is close to the edge of the unit cell. Regards. Have a good seasonal break.Axiosaurus (talk) 08:30, 18 December 2014 (UTC)

Global account[edit]

Hi Smokefoot! As a Steward I'm involved in the upcoming unification of all accounts organized by the Wikimedia Foundation (see m:Single User Login finalisation announcement). By looking at your account, I realized that you don't have a global account yet. In order to secure your name, I recommend you to create such account on your own by submitting your password on Special:MergeAccount and unifying your local accounts. If you have any problems with doing that or further questions, please don't hesitate to ping me with {{ping|DerHexer}}. Cheers, —DerHexer (Talk) 00:46, 3 January 2015 (UTC)

Fullerenes[edit]

Re. "Undid revision 641402623 by Ankababel (talk) conflict of interest, cite a review by someone else" -- this is an odd remark to make. In most or many cases only one review is cited. A review is a review -- it covers many viewpoints and should be impartial.Ankababel (talk) 14:03, 8 January 2015 (UTC)

Pulp and paper industry[edit]

Re. "(Undid revision 641569121 by Ankababel (talk) not encyclopedic content - there are lots of interesting debates)" -- this is just style, I removed the "interesting debate" phrase previously. Why don't you just rewrite? Anyway I've done it now. Mea culpa for using unfortunate phraseology. Or are you just anti-nanotech?Ankababel (talk) 14:14, 8 January 2015 (UTC)

Dear Smokefoot: Thanks for the comments. So far, the students are quite enthusiastic if a bit nervous. I am also new to this media, so I appreciate your comments and look forward to suggestions in the future!Dbzam (talk) 13:41, 12 January 2015 (UTC)

UG contribs to WP[edit]

Hello Smokefoot

I know that you've been using students to contribute to WP for several years, and I was wondering about doing the same. We're just setting up a new course here at Bristol on the theme of Chemistry in the Digital age, and WP seems like a good topic, especially as that's now the default source for anything they want to know. Would you be able to give me a quick rundown of what you do with them / potential pitfalls / benefits?

Thanks,

Chris (talk) 12:32, 14 January 2015 (UTC)

I would be glad to help. First of all, we contribute through a course that is mainly a lab (synthetic inorganic/organometallics for advanced undergrads). This Wikipedia article is worth about 10%. Here are some aspects:
  • I do ‘not emphasize Wiki-formatting'. This assigment focuses on teaching them to write about chemistry and learn how to copy-edit, not learn Wikipedia techniques (although they are free to do so, and many do). To this end, in the past few years, I have set up the articles, precluding their need to even register (I realize that Wiki-central command views student involvement as a recruiting mechanism but I have not seen that trend after going through hundreds of students). The skeleton articles that I establish, illustrate referencing, chem box, linking. You can see this approach with the history of iron boride. Similarly, we have shifted increasingly to article improvement, again avoiding their need to register) as illustrated by lead styphnate.
  • We try to write shorter articles and this is probably our greatest weakness compared to typical multi-page student essays where they learn a lot about a big area. The emphasis however is on editing as much as creating content.
  • Students work in teams. I have about 30 students and supervising 30 articles is too much work to do well (in the past courses we have uploaded many more). Employers of my students want them to demonstrate an ability to work as teams. I am highly focused enhancing student employability. Only a fraction are aiming for professional schools - and they tend to write on academic topics such as Transition metal alkyne complex, Nitrogen-15 NMR spectroscopy.
  • Students must get their draft article approved by me as a Word document before they can upload to Wikipedia. It is refining this Word document where they actually learn the most and where I do most of my work - about 2-3 drafts.
  • I de-emphasize graphics. Probably nonideal, but students are not very good at ChemDraw and I am picky. We could do more at pdb and csd images, but again this aspect of the course emphasizes writing not drawing.
  • We spend a lot of time figuring out topics. For some appealing topics we just cannot find good general sources, so we dont pursue those. We are increasingly turning toward improving existing articles because we are running out of topics and so many existing articles could use help in select themes.
  • Although the course is on inorganic/organometallics, I figure that for undergrads just learning to write about any chemistry is healthy, so we write about all sorts of topics. I also meet with them to identify their professional interests, the point being that articles might enhance their employment aspirations and hence their devotion to their topic. Some of their diverse interests have been in beer brewing (see Humulone), perfumery (2-Methylundecanal), pesticides (Pentachloronitrobenzene), antibiotics (Yersiniabactin), explosives (lead styphnate). These are employable topics in the US. Naturally, they write a lot of inorganicky articles too, which are not coupled to employment.
  • I prohibit students from discussing tox or safety or environmental aspects, despite the fact that I am a tree-hugger myself. Googling on chemical topics mainly turns up tox - safety - environmental content, often crufty, but I want them to write about hard core chemistry. Students are always ready to fill any article with all sorts of health and safety stuff - easy to get and easy to write about, but not very chemical (unless they figure out the chemical mechanism of tox, etc).

--Smokefoot (talk) 18:52, 14 January 2015 (UTC)

Thank you very much; I'll take that all into account. Chris (talk) 22:15, 21 January 2015 (UTC)

Silver(I) fluoride[edit]

Hi ! Thanks for your editing. I did reinsert the lab prep bit but maybe we should discuss this (I made a note on the talk) as I'm new to Wikipedia and not so au fait with you do articles. I'd be very grateful for any help ! --TatanyaGolding (talk) 09:48, 16 January 2015 (UTC)

Xenon Difluoride[edit]

Thanks for the pointers. I'm not sure if any secondary sources exist for XeF2 etching for MEMS. Maybe I should write that paper :) — Preceding unsigned comment added by KrisPister (talkcontribs) 21:47, 20 January 2015 (UTC)

looks like neat stuff. No chemist would expect XeF2 to be good for anything outside of research lab. --Smokefoot (talk) 23:02, 20 January 2015 (UTC)

My edit to 1, 1, 1-Trichloroethane[edit]

Why did you revert my edit? The words "dicarbon trihyrdogen trichloride" would actually be its chemical name using the correct systems. DudeWithAFeud (talk) 02:08, 22 January 2015 (UTC)

No problem. People dont use that name. Its not a big deal.--Smokefoot (talk) 03:03, 22 January 2015 (UTC)
The appellation "dicarbon trihyrdogen trichloride" does not specify where the chlorine atoms are located in the molecule. The 1,1,1- prefix specifies the three chlorines are located on the #1 carbon atom. The isomer 1,1,2-trichloroethane is also possible. 1,2,2-trichloroethane is the same as the 1,1,2- and so the lowest numbering is used. Similarly, 2,2,2- is the same as 1,1,1- and again the lowest numbering is used. The hydrogens are understood to be placed on the carbon skeleton as needed wherever there are no substitutions. According to the IUPAC naming system (IUPAC claims its naming system is the official one.), 1,1,1-trichloroethane is used. H Padleckas (talk) 06:23, 23 January 2015 (UTC)
... and again, people dont use that kind of name/appellation no matter how many numbers one puts before or after it!--Smokefoot (talk) 12:42, 23 January 2015 (UTC)