User talk:Smokefoot/TalkArch2011

organosulfates

Just wanted to say thank you, the additions on the page are looking really nice. I was stumped and trying to re-think the page.DF

Fluoride

I was curious how you thought links to reliable sources on a talk page were not constructive. Looks like it was an annoying anti-fluoridation sock but still. Vandalism? Shootbamboo (talk) 23:23, 27 December 2010 (UTC)

Please do not mislabel this as "vandalism". Note the link to AN/I here, and the comment that the IP was a sock of a blocked/banned user. --Ckatz^chat_spy 00:08, 28 December 2010 (UTC)

Good points both and thanks for taking the time to help with this theme. The fluoride pages have been pummeled for weeks by various sites, apparently all the same person or organization. The comment from Shootbamboo, is possibly more important because it touches on policy issues, vs my possibly trigger happy response to attacks on fluoride and water fluoridation. I consider the selective citation of scientific literature without context to be worst than vandalism, i.e. an extremely deceptive way of hoodwinking gullible public who are unfamiliar with the variable standards of technical journals. Edits emanating from or supporting the position of the Fluoride Action Network have increased their sophistication. This tiny fringe group gets 'fair treatment" through the creation of myriad articles in Wikipedia. As Shootbamboo knows well, tens of thousands of publications exist on fluoride - an extremely common element, and one can therefore find dozens of primary cites to prop up diverse perspectives (see the compressed list here). As I have explained here, I really feel that Wikipedia has, through its overgenerous sense of fairness and its unsophisticated understanding of the technical publishing, legitimized and even promoted seriously hurtful pseudoscience. Your guidance would be welcomed.--Smokefoot (talk) 00:46, 28 December 2010 (UTC)

Smokefoot, thanks for your vandal / sock fighting efforts. Now if only all these articles would be semi-protected indefinitely we could get back to doing something useful. -- Brangifer (talk) 01:42, 28 December 2010 (UTC)

Sourced POV pushing is harmful to the project, and harder to revert than nonsense, so I understand your feeling. My concern was that "Even harmful edits that are not explicitly made in bad faith are not vandalism" (says WP:VANDALISM) so in my mind it would be a bad idea to remove the comments completely by labeling them as vandalism. In my mind, removing the comments on the talk page might embolden POV pushers by making them believe there is a conspiracy against them to suppress science. But I tried to cite one of their own papers to highlight the uncertainty of the IQ/fluoride association (and also contrasted the science with a link to lead). Anyhow. Happy Holidays. -Shootbamboo (talk) 02:20, 28 December 2010 (UTC)

This made me wonder if I should reply, by explaining to the IP that it doesn't exactly follow Wikipedia:Talk page guidelines. But sigh, unfortunately I don't think taking my time by explaining how we are supposed to behave will likely result in a Wikipedian. -Shootbamboo (talk) 02:39, 28 December 2010 (UTC)

I mentioned this at your talk page, but just for clarity, I was asking Smokefoot if they should have really labeled the talk page stuff that was removed as vandalism in their diff. -Shootbamboo (talk) 02:43, 28 December 2010 (UTC)

No mistaken identity, Shootbamboo, although I see the mixup with the vandalism label. Note that the IP is a sock of a banned user, and as such not permitted to post or edit. Hence the removal. --Ckatz^chat_spy 02:48, 28 December 2010 (UTC)

Ah OK. That makes sense (on why to revert) on the talk page only though. I added that line in the article. Thanks. -Shootbamboo (talk) 02:52, 28 December 2010 (UTC)

Fortunately the infamous "fluoride spammer" has now received the hardest sanction possible here, a community imposed indef ban. That doesn't mean they won't try again. -- Brangifer (talk) 04:02, 4 January 2011 (UTC)

What I find really funny about this comment is that it resembles arguments used by the most radical anti-aspartame activists, and on discussion lists skeptics have responded to their bizarre statements by noting that their behavior shows what lack of aspartame can do to a person.....they start acting weird....;-) So it appears to be with fluoride.... - Brangifer (talk) 04:06, 4 January 2011 (UTC)

Essential fatty acids?

Are there really essential fatty acids or is this some sort of marketing ploy by health food vendors? I have been editing in that area and was surprised to read about them. I never ran into them in biochem classes. Thanks,--Smokefoot (talk) 23:49, 30 December 2010 (UTC)

Yeah, they really exist. You need at least one w-3 (one FA from that class) and one w-6 (one from that class) and you can make the others from them (a few carnivores species need more). Essential fatty acid deficiency was first seen in people getting total intravenous nutrition, where, for obvious reasons they put in only amino acids, sugar, vitamins and minerals (fat emulsions were quite hard to develop as IV formulas). The reason for the problem is that the body can make fats from sugars, but cannot introduce unsaturation closer to the end than w-9, and you NEED w-6 and w-3 fatty acids to make lipids (the w-3 DHA is your most common neural tissue fat).

I'll see what I can do to put in some general refs from academic nutrition books. There is some quackery out there (like pills that contain w-9 because olive oil is cheap) but most of the fish oil supplements are worth taking, actually, unless you eat cold water ocean fish regularly.

BTW, there is some evidence that that bad reputation of saturated fats are from experiments in which animals were fed only hydrogenated coconut oil for their fat source. hydrogenation destroys all essential fatty acids because it destroys all PUFAs. On such a diet, even DOGS get severe atherosclerosis, and they are species highly resistant to it (their HDLs are higher than their LDLs). So all this is quite fascinating-- some of we thought was bad effects of tropical ssturated fats, was from studies that accidentally caused EFA deficiency. SBHarris 23:58, 30 December 2010 (UTC)

thoughts on animations

Hi Smokefoot, We truly want to work with the community for our courses, and as we are about to try something new, I thought that I would consult you for your thoughts and ideas. We would like to take advantage of the new media allowances on Wikipedia and insert animations for readers to better understand the arrow-pushing process of mechanisms. We create animations using a gifbuilder, and I have added one here in EAS. What are your thoughts about these animations? and How can we best insert them/make them stick and for the community to accept them? Thanks for all of your help! MichChemGSI (talk) 07:32, 31 December 2010 (UTC)

Not my call what you do. The organometallic contributions have been somewhat narrow, allowing class priorities to trump the truth (insertion = migratory insertion, absurd) and good manners (overwriting). Check out this contribution from User:Tycarter under the explanatory note "Replaced revision to concerted mechanism with more detailed and scientifically accurate description.") "This mechanism [oxidative addition]] is often observed for the activation of homonuclear diatomic molecules such as H₂ and N₂ as well as for highly strained ring systems such as cyclopropanes." Brilliant. --Smokefoot (talk) 17:00, 31 December 2010 (UTC)

Thank you for the reason of the structure of the bifluoride anion: HF₂^-

Smokefoot, Thank you very much for your very judicious comment on the structure of the bifluoride anion in the ammonium bifluoride and the potassium bifluoride. It is true that HF is a very weak acid, simply because the fluoride mono-atomic anions is very small and strongly attracts the proton. As you very judiciously mentioned: fluoride is a strong base. I totally overlooked the text on top of the ammonium bifluoride page, simply because all my attention was drawn by the problematic systematic names in the diff view. It is the picture on Pubchem with the non-dissociated HF molecule that let me think more into detail to the structure of this compound and of the bifluoride anion. Quite logically, the considerable strength of the hydrogen bond between a small fluoride anion and a HF molecule explains the formation of the difluoride anion: F^- + HF —> HF₂^-. It is also well explained on the discussion page of potassium bifluoride. :-) Best wishes and a happy new year, Shinkolobwe (talk) 17:08, 1 January 2011 (UTC)

BioAs

Hello. By looking at your contributions it seems to me you are knowledgeable in the field of biochemistry. Your help in this very young article is most welcome and valuable. Thank you, --BatteryIncluded (talk) 01:45, 4 January 2011 (UTC)

Something needs fixing

Take a look at the this diff and the edit summary. -- Brangifer (talk) 06:10, 4 January 2011 (UTC)

[1]

Why do you hide your concerns in an edit summary? If you think it is OR, then you should raise the concern elsewhere, not in an edit summary. Also, if you think my picture is a scam, I could make a larger quantity, but I have a very limited supply of cobalt(II) chloride. --98.221.179.18 (talk) 19:19, 10 January 2011 (UTC) a.k.a. User:Chemicalinterest

The plan

I thought about doing it because that lots of things in the list of things in cigarettes isn't in the cigarette additives category page. — Preceding unsigned comment added by Ebe123 (talk • contribs) 16:13, 15 January 2011 (UTC)

Fluorine peer review

Hi Smokefoot, somebody reworked the fluorine article, If you like you can have a look if it is OK. Thanks!--Stone (talk) 23:38, 18 January 2011 (UTC)

Methylcobalamin

Thank you Smokefoot for leaving my entry. I was baffled as to why it kept disappearing. I am a very new newbie at all this as you will have realised. I did know not to put in any commercial references but have not been able to find anything published recently to suit. My aim with this entry is to entice a neuroscientist or equally knowledgeable specialist to edit this page with current information on what I have found to be a remarkable nutritional supplement. Kind regards (Everjanet (talk) 05:05, 24 January 2011 (UTC))

No problem and good luck with editing. It is usually a good to avoid giving or encouraging nutritional advice and helpful hints. Surprises many people, but there are guidelines for this encyclopedia, such as WP:NOTMANUAL, etc. --Smokefoot (talk) 13:36, 24 January 2011 (UTC)

Where HF comes from...

I tried to correct this mistake before but was reverted by the editor who hijacked this article. I also once thuoght that HF from fluoroapatite is the main source of HF, but it not. To quote from Ullmann's encyclopedia (emphasis added): "The industrial processes for the manufacture of anhydrous hydrofluoric acid are all based on the action of sulfuric acid on fluorite. However, phosphate rock, which contains fluorapatite, CaF2·3 Ca3(PO4)2, constitutes the most important natural reserves of fluorine..." --Smokefoot (talk) 14:21, 20 January 2011 (UTC)

Oh, no! I just now read this note, and I had just got through making the opposite change to harmonize all the articles on fluorite, the article on hydrogen fluoride, and so on. (I am not said "hijacking author"). If these articles are now all wrong and the major would source of HF is NOT a byproduct of phosphoric acid manufacture, they all have to be changed back. Let us get to the bottom of this issue, and fix it once and for all. Ullman's is an encyclopedia, and on this issue cannot be trusted as an ultimate authority. Let us find an authoritative source for world HF manufacture. SBHarris 19:26, 31 January 2011 (UTC)

A quick search: looks like the US, Europe and Japan are the world's fluorite importers, and yes, they do use it not only for smelting, but also production of HF and thus NaF, KF and F2. [2] SBHarris 19:42, 31 January 2011 (UTC)

doi:10.1162/jiec.2007.1075 They not only quote Ullmann's but also other sources. --Stone (talk) 20:31, 31 January 2011 (UTC)

Looks like a good source. I haven't read it yet, but the abstract says: To mention one example, a large percentage of the world demand for fluorspar could be supplied by the phosphate rock (fertilizer) industry, which currently dissipates a great deal of recoverable fluorine in waste phospho-gypsum. Emphases mine on COULD. Hasn't happened YET, apparently. SBHarris 21:53, 31 January 2011 (UTC)

Sorry, I am not paying much attention. Somewhere above on this talk page, an anonymous editor directed me to this [3] from the USGS), which says that 85 % of fluorspar mined is used for production of HF. --Smokefoot (talk) 02:07, 1 February 2011 (UTC)

The word somewhere before 85 % is domestic (only US) and the US is only 50% of the world market. So somewhere else the thing might look different. But in general most countries would simply dispose the phosphogypsum containing most of the fluorides and simply dispose it in a hidded place to make the process of fertilizer production cheap. Recycling of the fluorine from that source must be beneficial in an other reason, this might be environmental restrictions in the US. The article I posted above says that the phosphogypsum poses a big chance to avoide further mining for fluorite if the process becomes economicaly competative--Stone (talk) 15:52, 1 February 2011 (UTC)

Help on Copper(I) Cyanide...

Thank you for you tidying of my edits to the CuCN page. I am quite new to editing Wikipedia but would like get involved and any pointers or advice would be much appreciated. I believe that I can leave you a message here and you can leave a reply, I will find out soon...

I have a fair amount of experience of inorganic chemistry (in particular the cyanides of groups 10 and 11), structure determination using powder X-ray diffraction and total neutron diffraction diffraction. I have just completed my PhD "The Structure and Negative Thermal Expansion of Low-Dimensional Compounds". I am interested that you believe that my references are too specific what would you consider more appropriate? The articles I cite are in peer reviewed journals which I believed should be suitable as they are the most recent structure determinations.

On the CuCN page I have edited some points I am unsure how to reference:

• The colour of CuCN is pale yellow when supplied. Older samples are slightly green but have been stored in a damp environment. I have access to a powder diffractometer and all samples appear pure by PXRD.
• KCu(CN)2 is insoluble in water. There is an Inorg. Chem. paper which I can't find which states that both K2Cu(CN)3 and K3Cu(CN)4 are soluble. In my experience when dissolving CuCN in KCN solutions a ratio of 1:3 is required although this is likley to be concentration dependant.

All the best

Edd B —Preceding unsigned comment added by 134.225.50.57 (talk) 14:37, 3 February 2011 (UTC)

Well first of all, welcome and go for it. Wikipedia depends on experts, and there are several surprisingly sophisticated editors roaming around. Each has a slightly different idea of what we are supposed to be doing.

In general, Wikipedia prefers references to reviews and books, not journals. See WP:SECONDARY. It is not practical to do so always, but such broad overviews should be the default. Sharp's book on cyanide and Dunbar's Progress in IC for example. Otherwise we overload these articles with too much specialist info and we run the risk of Dr. XYZ citing all of his/her papers in Wikipedia (a vanity thing WP:COI).

My point on CuCN being cream coloured (probably white, actually) is that it is our responsibility to describe the colour of authentic material, not some old crappy samples. But I confess to being a purist. But CuCN is not green.

The main thing is to describe the broadest aspects of Cu-CN chem, but most of the editors here are academic. 99.9% of CuCN is probably consumed for some practical application, such as electroplating or polymerizing ethylene oxide, so to some extent, in my mind, the content should reflect the real world impacts vs some academic investigation of a new coordination derivative, which does not merit mention here.

Most important - go register. Not hard to do.--Smokefoot (talk) 15:28, 3 February 2011 (UTC)

I am in the process of registering, I had previously created an account which I lost the password for. I have written to you in the hope that I can get a better idea of what is appropriate and appreciate your time. I also understand that most people on wikipedia have a high level of knowledge in the subject about which they are writing. Both The Chemistry of Cyano Complexes, by Sharp and Cyanogen Compounds, by Williams are very good overviews but are quite dated and some of the information in them is incorrect. The review by Dunbar and Hienze is very informative and well laid out but doesn't cover the structures of the cyanides of groups 10 and 11 because it was written in 1997. I will however try in future to reference text books rather than academic journals.

On the colour, it is true that most d10 metal compounds are white (no possible d-d transitions) but I have never seen a pure white CuCN sample. My edits have been trying to reduce reference to it being green as I also believe that this page should reflect the true colour of a pure sample. I am unsure what most of the world CuCN is used for but I doubt that it is in electroplating or as a biocide as cyanide compounds have a bad reputation. As an Encyclopaedia I believe that the crystal structure and simple chemistry should be covered to the same level as in a text book is this correct in your opinion? —Preceding unsigned comment added by 134.225.50.57 (talk) 10:30, 4 February 2011 (UTC)

You dont really need much advice so good luck. I am pretty sure that it is indeed used in electroplating - if you get a chance look around for sources on applications. In any case, that is usually my angle. Absolutely the color, structure, and basic prep (or production route) should always be mentioned. When I get nervous are long list of coordination complexes. Good luck,--Smokefoot (talk) 14:53, 4 February 2011 (UTC)

Hope you like the new pictures and cheers for the push to sign up. — Preceding unsigned comment added by Bilbe85 (talk • contribs) 18:59, 28 February 2011 (UTC)

Methanofuran structure

User:Yikrazuul and I found some inconsistencies in your commons:File:Methanofuran.png structure (noted in the {{disputed chem}} box on that image-page). DMacks (talk) 21:26, 7 February 2011 (UTC)

Conducting polymers

I have followed this story for some time. All participants are PhD level scientists who overtime learned WP policies and stopped boldly pushing their edits through. Thus civilized communication is a must (you are a too valuable contributor to be lost in ANI threads, and time is too valuable for that when there is so much work to be done around). There might be WP:RS arguments against articles by Bolto and the melanin image, though even this is not that easy - Aust. J. Chem. is an obscure journal, but with an impact factor. I see no reason to dismiss books by Okamoto and Intzel. To me this is akin the carbon nanotube discovery, i.e. I have no doubt conducting polymers were studied and reported well before Heeger et al., but perhaps nobody listened to the reporters. Thus I would focus on NPOV reflection of the facts. Cheers. Materialscientist (talk) 00:15, 12 February 2011 (UTC)

Okay, I will let you deal with it and try to keep out of trouble. I have tried for years to get chemical editors to stand up to what I see as POV pushing by Pproctor and his cadre of editors who uniquely admire Proctor's now-forgotten advisor John McGinness.

• McGinness, who is not even mentioned in the Nobel citation (http://nobelprize.org/nobel_prizes/chemistry/laureates/2000/chemadv.pdf), apparently once described a device whose picture appears in the following pages: Organic electronics, Molecular electronics, Melanin, Conductive polymer, Organic semiconductor. This repetition seems like undue weight, and such imagery is invariably associated with a history section that denigrates the Nobelists.
• If one wants to go to old literature in a hunt for precedence, here's a good source of references: "Electrical Conductivity of the Perylene-Bromine Complex" Akamatu, Inokuchi, Matsunaga, Nature, Volume 173, Issue 4395, pp. 168-169 (1954). The Nobel citation also quote work from the 1850's on polyaniline.
• Thanks for the warning, --Smokefoot (talk) 04:34, 12 February 2011 (UTC)

Not a warning, just wanted to save your nerves - this is not the first or last POV-in-science case. You know this area better than I. What I saw is that some of those editors aim at promoting McGinness, and some at demoting Heeger et al. One way to quench promoters is to show that they did not event anything new, and all was done well before them. You are more than welcome to add on that. Do you know anything more on "as early as 1862 H. Letheby of the College of London Hospital, by anodic oxidation of aniline in sulphuric acid, obtained a partly conductive material which was probably polyaniline."? I'll check the 1954 Nature article on Monday (I've heard much of this before, but set aside when all that conductive polymer activity has stabilized a few months ago). Materialscientist (talk) 05:04, 12 February 2011 (UTC)

Uh, most of the recent activity on my part has been to post citations to highly-conductive polymers back to the 1960's (at least). Please explain how this "promotes" Mcginness' work done ten years later. As for Heeger et al, as several have noted, the prexistance of the field is the subject of a book chapter in a major text on the subject. In fact, if you have citations to highly-conductive polymers back to the '50's or earlier, you should post them. Also, editors should not delete material on the talk pages. Highly irregular and approaching vandalism, particularly if done to advance a POV. Nucleophilic (talk) 05:02, 27 February 2011 (UTC)

Cyclopentadiene as ligand

This edit is a pretty bold statement that Cp as a ligand gives compounds that are not useful except in teaching labs. I don't think Tebbe's reagent is used as a teaching-lab example, but it (and related) seem quite popular in research labs. In general, CpNa appears to be a commercially significant chemical. I remember a lecture a few years ago where a researcher at a scale-up/pilot plant was complaining about the quality of that chemical being variable from drum to drum. Do you have a cite that CpM complexes are of little commercial value? DMacks (talk) 16:56, 12 February 2011 (UTC)

Well maybe I went from bold to brash... I will tone down my provacative comments. I equate teaching and research labs. My intended point is that no C5H5 complexes is useful in commercial catalysis. I have been looking for examples, but all one finds is academics talking about how important Cp complexes are... Thanks for the help.--Smokefoot (talk) 17:08, 12 February 2011 (UTC)

Looks nicer now. I usually see a pretty big distinction between teaching labs (maybe as high as US masters-degree level) vs research (including graduate-level synthetic labs and pharma med-chem)--all "basic science" is about the only similarity. I don't know about catalytic uses, but doi:10.1021/op034180j appears to be a process-chem stoichiometric use. DMacks (talk) 21:17, 12 February 2011 (UTC)

If the question is applications of cyclopentadienyl complexes (as opposed to cyclopentadiene complexes) then the extensive work on metallocene anti-tumour agents for medicine might rate as "useful". EdChem (talk) 05:05, 13 February 2011 (UTC)

The anti-cancer aspect went nowhere and is dormant. It is a curious that so far as I can tell, no Cp complex per se is commercialized, with the possible exception of ferrocene as an antiknock agent. For substituted Cp compounds, methylcyclopentadienyl manganese tricarbonyl and one or two derivatives of zirconacene have been commercialized as antiknocks and as alkene polymerization catalysts, respectively.--Smokefoot (talk) 14:51, 13 February 2011 (UTC)

Thanks (and other thoughts)

Wanted to follow-up your talk page comments here and thank you again for your advice. I see from the conducting polymers section above what you meant about how naming people in sections on the history of a science can get passions aroused. I also enjoyed reading the 'hall of strangeness' on your user page, and the bit about water fluoridation brought a wry smile to my face, though mentioning iodised salt might be tempting fate (we do have an article on it, but not as much turbulence around it as you noted).

If you are still interested in the rewrite of the physical chemistry article, I'm going to make some notes on the talk page in an attempt to identify what the main sections should be for such an article, and which sub-disciplines don't warrant a separate section, as I suspect the current arrangement confuses things somewhat and gives some areas undue emphasis. My main problem is getting an accurate overview of what the current sub-disciplines are, especially given the rapid rate of fragmentation and specialisation over the last decade or two (I think it would be fair to say that has been the case). Essentially, I'm looking for a summary of how physical chemistry has changed over the last 20 years. If I'm better off asking DMacks or Materialscientist, I'll do that, but I wanted to ask you first as you were kind enough to comment at the article talk page. Carcharoth (talk) 01:13, 16 February 2011 (UTC)

Good luck. I am out of my depth on physical chemistry. You might not find many editors willing to help. Each doed our own thing around here. My closing advice are to (1) avoid discussing people - although they are fun and easy to write about - stick to substance, and (2) realize that Wikipedia is not a US product.--Smokefoot (talk) 03:15, 16 February 2011 (UTC)

YMMV, However, many readers come to wikipedia for information on the history of a particular technology. Further, standard practice in scientific review articles is to insert a short history of the field. And yes, priority can cause controversey, which is why there is a particular need for wp:reliable sources to resolve such issues, particularly secondary sources. But in the presence of such, what is the problem ? Nucleophilic (talk) 05:20, 27 February 2011 (UTC)

Well we do not agree on this theme but it is not that big a deal. Just slightly annoying that Pproctor and his close allies have been on a multi-year campaign to bring even a hint of credit to his now forgotten PhD advisor. But no big deal. Life goes on and we all know about crybabies.--Smokefoot (talk) 15:36, 27 February 2011 (UTC)

I'm a "close ally" of nobody. For some reason, you keep making this entirely-straw argument. Unfortunatey, it is impossible to debate a straw argument, except by continually pointing out that it is straw. Mostly, I have posted wp:reliable sources antedating the work of McGinness 'et al' by more than a decade. Entirely contrary to your assertions, this has progressively pushed any priority claims these workers might have ( not that they really make any, for this at least ) for the discovery of highly-conductive polymers even further away.

The apparent true objection seems to be that such cites also call into question the "discovery" part of the 2000 Nobel chemistry prize. There is now general agreement that this assignment was erroneous. In fact, the Nobel committee missed an entire field, not just a paper or two. As I have noted, such secondary sources include an entire book chapter on this matter in a recent important textbook in this field. I'd be happy to debate this issue, although the WP:RS speak for themselves. Nucleophilic (talk) 18:09, 27 February 2011 (UTC)

That pesky Nobel committee, they keep blowing it don't they. There's also the case of Lauterbur and Mansfield, another crybaby case...--Smokefoot (talk) 18:51, 27 February 2011 (UTC)

It is true that the Noble committees make a lot of subjective judgements. I would not deign to dispute these. However, they are human and make human errors. Assignment of "discovery" here is easy to falsify. All you need do is show that somebody reported the same thing previously. In the case of conductive polymers, there were many such reports, going back over a decade, at least.

It is hardly "crybaby" to note this. Interestingly, by the Danish definition of science fraud ( "...a false credit or emphasis given to a scientist" ) deliberate false assignment of discovery credit is misconduct. The Swedish definition is based upon the Danish one. Check it out. Nucleophilic (talk) 22:04, 27 February 2011 (UTC)

Talkback

Hello, Smokefoot. You have new messages at Phearson's talk page.
Message added 05:33, 14 March 2011 (UTC). You can remove this notice at any time by removing the {{Talkback}} or {{Tb}} template.

Change you made to Iodine

Please contribute to the discussion at: Talk:Iodine#Why_change_heading:_.22Protection_from_radioactive_fallout_.3D.3D.3E_Human_health.22.3F Ottawahitech (talk) 14:12, 15 March 2011 (UTC)

Aqua ions

My first draft is now ready at User:Petergans/m. Please have a look at it an edit/comment as you see fit. I've run out of ideas on

• lead
• occurence in nature/ uses
• categories
• more pictures

Spelling is a bugbear. I have run a spell-checker, but my typing is terrible, so I expect some errors to have been missed. Petergans (talk) 16:56, 17 March 2011 (UTC)

Fukushima – Zirconium oxidation – Hydrogen production

Many thanks for your prompt review of the pages dealing with Zirconium alloys and Zirconium in relation with the reaction of Zr alloys with water at high temperature. Appreciated. Best regards, Shinkolobwe (talk) 15:22, 20 March 2011 (UTC)

When you have some time

Perhaps you can take a look at Tolman electronic parameter. Don't know whether Chadwick A. Tolman's still alive and I can't find much. Maybe you have more to say. --Rifleman 82 (talk) 01:36, 22 March 2011 (UTC)

Yes, that TEP articlle is overdue and very welcome. Great job. The Muetterties thing is by a researcher at DuPont who is an uncalibrated, tone-deaf cheerleader for all things that happened there in the earlier times.--Smokefoot (talk) 12:42, 22 March 2011 (UTC)

Ah okay... thanks! --Rifleman 82 (talk) 14:54, 22 March 2011 (UTC)

I also compressed the Muetterties report. BTW, thanks for your help with the MOS. --Smokefoot (talk) 17:05, 22 March 2011 (UTC)

Thanks for your help & comments and you're welcome. Always a pleasure working with you. --Rifleman 82 (talk) 23:57, 22 March 2011 (UTC)

WP:NOTNEWS

For future reference, WP:NOTNEWS is talking about article level notability, not individual pieces of information in an article. That's why that particular entry links twice to notability. I included 3 different kinds of crimes committed with clear citations for both. The removal of the second two pieces of information has now left the introductory sentence making uncited claims. Sorry, but this is as often used plot device in fiction and as talk has indicated many people have shown up wondering about it. Since it's something that actually happens, and has been happening on record for over a hundred years, a couple sentences won't cover it.--Crossmr (talk) 22:38, 30 March 2011 (UTC)

Well, I disagree. Lists of crimes committed by various chemical compounds is not encyclopedic in my book.--Smokefoot (talk) 00:00, 31 March 2011 (UTC)

Giving 3 examples of 3 different kinds of crimes to indicate usage is hardly any kind of comprehensive and extensive list.--Crossmr (talk) 07:59, 31 March 2011 (UTC)

Ferroverdin

Hey SF

Trying to draw pictures for your article. The charges don't balance (and the N-O ligand is a little uncommon...) It should be N-O⁻? Anyway, that makes it short of a counter cation. What is typical? I tried looking at the Japanese paper but I suppose biologists don't worry about that too much. --Rifleman 82 (talk) 00:08, 7 April 2011 (UTC)

You got it, as far as I can see. Two resonance structures, one quinone-like with neg charage on nitroso oxygen and the other phenolate like with neutral Ar-N=O. So the ferrous-tris chelate complex would be anionic. I am also worried by the proposed enol substituent on one ring. Thanks for all of your help with these things. BTW, I guess S-methylmethionine should not hava a chembox, a sulfonium-zwitterion with an undefined counteranion. Another one I ran into today is auramine O. --Smokefoot (talk) 03:28, 7 April 2011 (UTC)

I usually just give it a chembox of a representative compound which exists... but some newbies aren't respecting what we've agreed upon - cations radicals and other fragments which don't exist in isolation don't get a chembox. I'll take a look. Thanks. I think a problem is biologists don't worry about charges needing to be balanced. The same way in biology electrons and protons appear and disappear out of nowhere... --Rifleman 82 (talk) 04:41, 7 April 2011 (UTC)

Disulfur

You might want to consider submitting it for wp:DYK. Cheers, Nergaal (talk) 06:00, 7 April 2011 (UTC)

Zinc sulfate

thanks for the correction I really appreiciate it--Geo7777 (talk) 15:02, 10 April 2011 (UTC)

SHOP

I dunno, that's what the J. Chem. Ed. article says, that cobalt isomerizes it to the alpha olefin. I'll go take a look at the cited works when I have a little time. --Rifleman 82 (talk) 02:22, 18 April 2011 (UTC) Well it's probably true then. I had always assumed that there basically were no internal olefins after the oligomerization. I was going to mention SHOP in olefin metathesis, but that article is awkward to work with. I wonder how such alpha-olefins are made now that SHOP has been phased out, it appears. --Smokefoot (talk) 03:00, 18 April 2011 (UTC)

I am not sure what the question really was, but the process works in a way that ethen is oligomerized with the Nickel catalyst and eliminated as alpha olefine. The higher alpha-olefins, ie C20, are isomerized to the internal olefin. The internal olefin is then ethenelyzed (metathesis with ethene) to shorter chain alpha-olefins. -- Linksfuss (talk) 19:24, 20 September 2011 (UTC)

Prussian blue structure

You may well be correct about the structure - I constructed it from the SMILES, if the structure is wrong, can I suggest you delete the SMILES as well.  Ronhjones  ^(Talk) 22:26, 21 April 2011 (UTC)

Student projects

Smokefoot, we need to continue our discussion of your intervention in the (erstwhile) student project article on Nitrogen Flow through Metabolism in my talk page. Please respond there. By the way, reading your talk page reveals that you are quite opposed to the spirit of Wikipedia: School and university projects and Wikipedia: template for educational assignments. UM BIOE120 Instructor (talk) 05:43, 23 April 2011 (UTC)

Jones oxidation

Any reason for changing my balanced equations there, or just an overwrite with an off-line version? Materialscientist (talk) 23:34, 25 April 2011 (UTC) Here is what I corrected from (I didnt know it was yours):

HCrO₄^– + RR'C(OH)H + 6 H⁺ + 2 H₂O → [Cr(H₂O)₆]³⁺ + RR'CO

Incorrect stoichiometry and doesnt balance. The oxidation of an alcohol to a carbonyl is a 2e change and the Cr(VI) is a 3e oxidant. And then this one

HCrO₄^– + RCH₂OH + 3 H⁺ + 3 H₂O → [Cr(H₂O)₆]³⁺ + RCOOH

Again, incorrect stoichiometry and doesnt balance. The oxidation of an alcohol to a carboxylic acid is a 3e change.

Here are the equations that I revised to:

2 HCrO₄^– + 3 RR'C(OH)H + 8 H⁺ + 4 H₂O → 2 [Cr(H₂O)₆]³⁺ + 3 RR'CO

HCrO₄^– + RCH₂OH + 4 H⁺ + 3 H₂O → [Cr(H₂O)₆]³⁺ + RCOOH

I think htat my revisions are balanced, but I often make mistakes too. At least the charges are. More importantly, the stoichiometries should differ so that readers understand that the former is a 2e change and the latter is a 3e oxidation. But I am open to suggestions. No ill-will was intended by my edits. I am kinda trained in this area, but highly fallable. --Smokefoot (talk) 00:23, 26 April 2011 (UTC)

Sorry, I entirely forgot about charges, thus both sets are unbalanced, but I'll fix that. I routinely replace journal references with {{cite journal|doi=...}} or {{cite journal|pmid=...}} and then run citation bot over - the bot expands the refs. While I do understand the (numerous) subtleties of such reformatting, in short, it allows to keep refs in a bot-readable format and therefore eliminate human errors. This is only useful for journals, and maybe books. Cheers! Materialscientist (talk) 00:37, 26 April 2011 (UTC)

I think my set is balanced:

2(1-) + 8+ == 2(3+)

(1-) + 4+ == 3+

About the bot thing, I prefer to read the citation without clicking on a link. I suspect others do too. Even if there is a slight risk of typo's. The only typo's that matter would be in the DoI. But maybe I am missing something.--Smokefoot (talk) 00:45, 26 April 2011 (UTC)

Your 2nd equation was unbalanced on hydrogen. I hope I've fixed that in the article. On refs: I think you were looking at an old, cached page - after the bot expansion, the refs would almost look the same, but the bot would copy/paste all other parameters (numbers, names, etc.) from doi. The bot still has problems (e.g. it can't parse some special symbols in author names and it does not use sub/super scripts in formulas), but they are fixable. On the other hand, I saw too many refs which were inconsistent or plain wrong because of human errors. Materialscientist (talk) 01:12, 26 April 2011 (UTC)

Well, I have no idea whether those equations are correct, but I'm pretty sure my math was correct (after you pointed me to the charges). Materialscientist (talk) 01:17, 26 April 2011 (UTC)

Hexamethylbenzene

Thanks for the quick fix! DMacks (talk) 16:26, 30 April 2011 (UTC)

These young editors put all kinds of weird stuff into these articles. They just dont know the language and terminology, which is kind of the point. But after they upload, they walk away, so I need to be careful that we dont transmit bad info. Thanks for catching the mistake. I have spent several days in cleanup mode.--Smokefoot (talk) 16:32, 30 April 2011 (UTC)

I don't have a lot of time, but could probably do some cleanups on one or two (now that Jones isn't such a mess!) if you're overflowing with this. DMacks (talk) 04:22, 1 May 2011 (UTC)

Kind of you to offer. Thanks to the active editing by you and others (Rifleman, Edgar), many serious problems have been addressed. Yersiniabactin and selenourea are two that need an alternative set of eyes. We have a longish article on leather tanning coming. --Smokefoot (talk) 13:28, 1 May 2011 (UTC)

Common reagents

Thanks for your input on Common reagents. However, I have a few concerns. The article is obviously not original research. All the information can easily be found from reputable sources and from elsewhere on Wikipedia. Its just condensed and organized into a list for ease of reference. Also, I'm not sure if the comment about the chemist thing is either appropiate or neccesary. Please refrain from making unconstructive and useless comments. On another note, I can see the usefulness of merging Common reagents with Reagent, but I think it would be better just linked to it. I hope I haven't offended you. Explodo-nerd (talk) 15:54, 4 May 2011 (UTC)

In my view, the article is poorly conceived by someone with little experience in a lab (acetylene, sodium amide, terpentine are common reagents?). It is also original research, because someone invented the list on Wikipedia. No great harm in this kind of thing. Those are my views, good luck with your editing. --Smokefoot (talk) 17:21, 4 May 2011 (UTC)

Edit summary

This edit summary is priceless! You made my day. --Ben (talk) 15:52, 16 May 2011 (UTC)

Fluoride toxicity

I tracked down some information on fluoride doses and added some information to fluoride toxicity. Quick question, does Ullmann's Encyclopedia of Industrial Chemistry really state 1 g of sodium fluoride is lethal? i.e. that would be 6.4 mg/kg of elemental fluoride (in a 70 kg adult), Seems quite low when children typically tolerate up to 8.4 mg/kg of elemental fluoride, i.e. that dose in children only produced mild self limited GI effects.[4]. Could you check that for me? If correct I guess you can add it back but I think it may be wrong. Also the fluorine page does not make any sense (i.e it states 28 milligrams per kilogram of body mass (5–10 g for a 70 kg human)) this doesn’t add up, perhaps we could use the information from fluoride toxicity in fluorine as well. Cheers Mr Bungle | talk 22:13, 18 May 2011 (UTC)

I don’t care enough about fluoride/fluorine (or Wikipedia really) to continue discussing it on a talk page, I saw a glaring error in a fluorine, a document about to become “featured”, and fixed it, I was then reverted and should have just left it at that. Probably against my better judgement I investigated it some more and have fixed it up again. Discussing it further on the talk page will probably just attract anti-fluoride nutters and their discussion of some useless study in the journal Fluoride. Similarly Sax and RTECS animal LD50 data is largely irrelevant to human clinical toxicology. As long as Ullmann's doesn’t say 1 g is lethal then that will probably do it me for contributing to fluoride doses. Feel free to follow it up more if you think it needs it. Mr Bungle | talk 04:50, 19 May 2011 (UTC)

Labiblia (talk) 18:33, 30 May 2011 (UTC)There are leading scientists that are now saying sodium fluoride is harmful for you if ingested in any quantities. Why do you insist on having a straw man argument and use name calling in place of real science? Sodium Fluoride is harmful for humans period and it's bio-cumulative. Would you like me to share with you valid studies on the subject for discussion?

Tolman

Chad is alive and well in Wilmington DE. He is a frequent writer on global warming. Anything you would like me to update? I am in touch with him on a monthly basis. Littelinfo (talk) 02:02, 8 June 2011 (UTC)

Muetterties

Glad to hear that I am "an uncalibrated, tone-deaf cheerleader for all things that happened at DuPont in the earlier times." Nice to know that the work is appreciated. Yes, I started a number of DuPont-related items because thatis what I know. But I also started some Monsanto, Shell Emoryville and other items. I happen to like chemical research and I happen to be old. And it cannot be too hard to figure out who I am.

All of the Earl references were in response to a deletion of an item because it was under-referenced. Just wanted to see what would happen. Guess you demonstrated it to me, though there are a number of references I would have retained. I didn't particularly like Earl, but I though he deserved mention in Wikipedia. I don't think of it as chearleading. And I don't understand the tone-deaf part. In fact, I am quite musical. Please explain. Thanks.

Littelinfo (talk) 02:02, 8 June 2011 (UTC)

Yes, in my opinion, your writings about duPont were cheerleading vs conveying information. Not a crime, but bordering on tone-deafness with regards to an encyclopedia. As I recall, the article on Muetterties listed every publication, which is probably inappropriate here. Other venues/blogs exist on the web for homage. Best wishse with your editing, --Smokefoot (talk) 03:00, 8 June 2011 (UTC)

I prefer conveying information ina positive manner to being drab and encyclopedic. I admit that I would go insane using the style of an encyclopedia at all times - not my thing. I try to initiate articles and and get new thread going in the hope that other will fill them out and make their own contributions. I try to provoke contributions. I generally appreciate the efforts of the Wikipedia Gestapo who enforce the rules and make my work better. Yes, that was every one of Earl's publications. In response to having an item completely deleted for lack of sufficient references, I wanted to see what would happen if I did it and I got an answer. The first Earl article was a stub hoping that some of his students would rise to the call because I was not all that interested. They did not. I am also trying to get Maurice Brookhart to improve his own article, but he is not into computers. My new article on the A. I DuPont Hospital has generated no response from them though they were up at one point in the past and removed because the writer was doing an advert for the hospital. Shell Emoryville is working pretty well as is Mound Laboratory. I think my piece on Frolic Weymouth is pretty good. Littelinfo (talk) 18:04, 8 June 2011 (UTC)

Proposed Image Deletion

A deletion discussion has just been created at Category talk:Unclassified Chemical Structures, which may involve one or more orphaned chemical structures, that has you user name in the upload history. Please feel free to add your comments.  Ronhjones  ^(Talk) 23:06, 10 June 2011 (UTC)

Patnaik

Hahahah...sorry! No, I was just checking some preparations on Wikipedia, but I thought they were lacking in information... so I tried to find more about them in another source, 1963 Brauer wasn't so good as 2005 Patnaik, i didn't looked it up on Vogel or Kirk-Othmer. BTW, why "obscure"? Gecg 01:17, 16 June 2011 (UTC)

Vandalism

It's not vandalism unless it's malicious. Yeah, I changed the spelling, sorry, my mistake. See quote below from official Wikipedia policy:

"Vandalism is any addition, removal, or change of content in a deliberate attempt to compromise the integrity of Wikipedia. Examples of typical vandalism are adding irrelevant obscenities and crude humor to a page, illegitimately blanking pages, and inserting patent nonsense into a page. ... Even if misguided, willfully against consensus, or disruptive, any good-faith effort to improve the encyclopedia is not vandalism. Edit warring over content is not vandalism. Careful consideration may be required to differentiate between edits that are beneficial, detrimental but well-intentioned, and vandalizing. Mislabelling good-faith edits as vandalism can be considered harmful."

It would perhaps be in... hem hem... someone's best interest to put on their glasses and read those last two sentences again. We must carefully consider edits before we mislabel them as vandalism, right? We wouldn't want to harm anyone, would we? Somebody needs to apologise to... hem hem... somebody else for harming his reputation. Being accused publicly of vandalism like that makes people inclined to fast and wrong judgements.

--Nmatavka (talk) 20:26, 20 June 2011 (UTC)

I encourage you to speak to your parents or one of your teachers... They can explain "good faith" is not changing the spelling on references to suit your preferences. The titles simply are titles... Good luck with that.--Smokefoot (talk) 02:40, 21 June 2011 (UTC)

Request for comments on a proposed article

Hi Smokefoot. After seeing the recent edits to the clothianidin page, I decided to take the first step in removing the (biased, IMO) presentation of current events from it. For starters, I've posted a proposed article on the 2008 incident in Germany in my sandbox and would appreciate comments from you or anyone else with a NPOV you care to share it with. If you all are fine with it, I'll make it live then proceed as I described on the clothianidin talk page. Let me know what you think. Cheers --USEPA James (talk) 17:39, 15 July 2011 (UTC)

good luck, but you may encounter resistance from other editors. Many editors (few of whom know a lick of chemistry, toxicology, or microbiology), view Wikipedia as a forum for expressing their concerns/anguish about environmental/health impacts. And many of the same editors also view dispassionate descriptions of these same chemicals as pro-industry or mal-intentioned somehow. --Smokefoot (talk) 18:01, 15 July 2011 (UTC)

What you wrote looks good to me. --Smokefoot (talk) 18:08, 15 July 2011 (UTC)

Thanks. That's what I'd expect a "pro-industry" hack to say about "somebody pushing an official government POV."  ;-) Do you recommend that I share it with the group discussing current events? --USEPA James (talk) 18:35, 15 July 2011 (UTC)

recent edits

Hi, thanks for the feedback. I reviewed my edit and I believe you are correct and I removed the parts you mentioned. I'd rather you write directly at the articles in the future. Best, Gandy Gandydancer (talk) 00:21, 20 July 2011 (UTC)

Metal_bis(trimethylsilyl)amides

New article. Would you mind taking a look? --Rifleman 82 (talk) 06:47, 20 July 2011 (UTC) Thanks! --Rifleman 82 (talk) 19:01, 20 July 2011 (UTC)

Personal attacks

This edit summary is absolutely unacceptable. You may be blocked for this. I have seen other comments on your talk page (like [5]), and you need to stop - comment on the content and not the contributor. I suggest you review WP:Civility and WP:No personal attacks. Your edit is disputed at Talk:Coordination complex.Jasper Deng (talk) 16:36, 5 August 2011 (UTC)

If you choose to edit an article about which you know nothing and have nothing constructive to contribute, such as the removal of content, your action is tantamount to vandalism. My edit comments might have been intemperate, but your actions were potentially worse since you inflict your ignorance on many readers. I inflicted my bad temper on you.--Smokefoot (talk) 14:23, 6 August 2011 (UTC)

Exactly the kind of thing that must stay off Wikipedia. Calling me ignorant actually is pretty wrong, I have learned my chemistry. Please review WP:AGF again. I actually know what I'm doing when I edit articles, you know. Please consider this your final warning for personal attacks.Jasper Deng (talk) 18:08, 7 August 2011 (UTC)

Jasper, you're not an administrator, so unless you have one in your pocket, it's inappropriate to do a "final warning" on anybody. Smokefoot, anybody who doesn't have an advanced degree in chem (which includes me, who only have a B.S.) is a sort of "self-appointed expert." We do the best we can. It's best not to use that kind of language as it's inflammatory. Jasper: accusations of ignorance are not personal attacks, inasmuch as we're all ignorant of most things. It's the normal human state. Rather than deleting the line, you should have added a "citation needed" tag. Smokefoot, the statement is technical enough that you probably should have put in a citation to begin with, or (at least) not been offended if somebody asked for one. I do understand you getting a bit offended at a removal of information that is not obviously wrong, by somebody not obviously expert, simply because they don't know if they believe it. If we did that, we'd have to delete most of Wikipedia. There's time for this, as this isn't a BLP.

In summary, as a disinterested onlooker, you're both somewhat out of order, and both of you could play more nicely. It's not worth this drama. Jasper, don't delete unsourced non-BLP info without asking for a cite politely. Smokefoot, re-add such deletions WITH a cite, at least the first time, without saying anything TOO irritating. Finally: Jasper Deng, if you're going to act like this, you'll never make it to administrator. Not that I see why anybody would want to be one. SBHarris 18:34, 7 August 2011 (UTC)

Thanks for the helpful advice. Oh well, a suitable salve is to add content...--Smokefoot (talk) 18:49, 7 August 2011 (UTC)

Ad:My welcome and advice

Hi. First of all thank you for your advice. I'm not totally new wikipedian, but my contribution is mostly on polish wikipedia. The rules are a bit different in those two language versions of wiki. What I like most about this encyclopedia is that many specialists write articles in areas in which they are experts. This is why sometimes they need add a sources/citations of their own papers/articles. I think that this is right and even desirable. Such approach ensures the correctness of the content of articles. By the way, I have a question: Should I respond on my or your discussion page? Finally, I would like to apologize for the language errors if I made. My English is not perfect. Regards --Danielchemik (talk) 20:42, 9 August 2011 (UTC)

Notability of a chemical

What criteria are there for assessing the notability of a chemical?For example, is francium chloride notable enough to deserve an article?--MagnInd (talk) 15:15, 26 August 2011 (UTC)

In my book, if the compound is real and simple, useful, or widely occurring, then it is notable. Unknown or barely known species can be important in some pedogical or theoretical senses, so exceptions exist. Problems arise if too many theoretical species make it into Wikipedia. I mean, one could write about sodium dichloride, for example, and I am sure articles exist on such topics. Just one person's views, of course. --Smokefoot (talk) 02:39, 27 August 2011 (UTC)

Re: WP does not really seek primary references ...

Hi Smokefoot, Sorry for putting this in your "inbox" again. Thank you for your comment. I might have been mislead by the primary references that had already been given in this article. Nevertheless, I think the line I added will be of wide general appeal. Specifically, the [4+1] cycloaddition between isocyanides and tetrazines is a reaction that has been known for decades and it is one that is quite specific to isocyanides. Recently, the reaction was used to convert isocyanides into carbonyls and also in click-chemistry. Thus as a PhD level chemist I believe that my addition not only serves as a good example in the isocyanide reactions section but also provides cutting-edge knowledge. Maybe the addition that I had made could be improved by adding a secondary reference (e.g. )? It would be a shame not to include this important information, but I can of course understand your point of view. Will you please let me know what you think. This will not only make the WP chemistry section better but also give me guidance for future editing efforts. Many thanks --Chembio1000 (talk) 17:53, 30 August 2011 (UTC)

Re: Cyanide

Concur that the pages cyanide and cyanide poisoning are mature. That does not change the fact that some of the information is incorrect and misleading. I was not aware there is a policy that involves the talk page. I will use the talk page from now on. Thank you for your courteous response.

I have a great deal of personal experience from chronic workplace cyanide poisoning that required considerable research, legal assistance, and medical treatment. Wikepedia is one of the information sources used by my former employer to point out that cyanide exposure is not a serious safety concern. The information provided by wikepedia should be somewhat credible and not misleading.

I hope this finds everyone well. Best regards.Nanoatzin (talk) 03:57, 8 September 2011 (UTC)

Thanks for the note and the courtesy. Comment though - editors with a "great deal of personal experience" can add poor information often based on their strongly held misunderstanding(s) of the subject, i.e. they can be blinded by the confidence they have in their own experience. Editors also who are most determined to help readers are also problematic in that their earnestness can fogs their understanding. So I encourage new editors to be careful and consult on technical subjects. But good luck, --Smokefoot (talk) 12:59, 8 September 2011 (UTC)

Erbium oxide

We have to keep article history, which is why pages are almost never moved by copy/pasting. We've got many admins at WP:CHEM, ask anyone to move over redirect when needed. Cheers. Materialscientist (talk) 13:07, 5 September 2011 (UTC)

Oh, sorry about making a mess. I realized as soon as I saw your work. My apologies. My recommendation is to go after ever lanthanide oxide and remove the names with "(III)." Exceptions exist for "salts" where alternative oxidation states are known or likely, but we might review them. --Smokefoot (talk) 13:13, 5 September 2011 (UTC)

(talk page stalker)You may want to exclude Samarium (has both +2 and +3 quite common, not sure for the oxides though), and include yttrium and scandium, the others have a very strong majority to +3. --Dirk Beetstra ^{T C} 13:18, 5 September 2011 (UTC)

(ec) I'm going off-line shortly. Quite possibly you can move those other articles yourself - it depends how many edits were made to the redirect page (try moving and overwriting the redirect page when asked). Those which you can't move, you can list, and then I or any other (WP:CHEM) admin will help (here is Beetstra, for example :-P). Yes, some lanthanides have non-negligible +2 and +4 states, but note the aluminium oxide redirecting solution - not sure about the best approach here. List_of_oxidation_states_of_the_elements used to be more or less accurate. Materialscientist (talk) 13:25, 5 September 2011 (UTC)

Zirconium

[6] Not just oxide, but alloys too (e.g. [7]). I have no time right now to fix that, but you are welcome ;-) Materialscientist (talk) 12:33, 20 September 2011 (UTC)

Thanks for helping and let me know if you have more suggestions. --Smokefoot (talk) 00:22, 21 September 2011 (UTC)

Metal carbonyls

Hi Smokefoot, I am currently working on the expansion of the deWP article about metal carbonyls. I have already used your photo of the diiron nonacarbonyl in the article. I noticed that you placed a lot of metal carbonyl drawings on Commons and I wonder if you have by chance any more photos of metal carbonyls crystals or drawings like the metal-CO-bonding (like here? I would like to use them to illustrate the article. Please let me know, thank you. Regards Linksfuss (talk) 19:15, 20 September 2011 (UTC)

I do not have many photographs, but lots of ChemDraw. Let me know what you think we need. Solid Fe3(CO)12 look like coal, although a nice solution would be more informative. If I get a photo of some Fe(CO)5, I will leave you a note. --Smokefoot (talk) 00:22, 21 September 2011 (UTC)

No worries if you have no more photos. I would like to include a drawing of the molecular orbitals of the metal-CO-bonding like in the drawing in the link above. If you have something like this I would appreciate it. -- Linksfuss (talk) 19:41, 21 September 2011 (UTC)

Thank you a lot. I took the third one (see here), looks good! -- Linksfuss (talk) 19:26, 22 September 2011 (UTC)

Sodium fluorophosphate Toxicity

I understand why you removed the discussion section on it but there were still two important points in there that have not been addressed but need to be:

1) The LD50 in all MSDS sheets and reputable sources (including the one the wikipedia article currently cites (reference 4)) should be 0.57g/kg (As based on the rat toxicity). The current 0.9g/kg listed on the wikipedia page is incorrect and has no data to support it including the reference it cites which clearly says otherwise. To not change this is to knowingly lie.

2) If one reads the official MSDS (or the reproduced one currently linked from the Wikipedia page as reference 4) it is pretty clear that very little is known about the majority of the toxicity, health, or safety effects of this compound. This is more or less openly stated in the MSDS sheet and all other official literature regarding the compounds handling. The wikipedia article does not reflect this in its toxcity section but should, as it is these are the currently accepted truths on this compound as reflected in the actual literature and documents including those already referenced by the wikipedia page.149.155.2.228 (talk) 12:31, 10 October 2011 (UTC)

Thanks for the note. The talk pages for the fluoride anions often become forums for what they call 'soapboxing" around here. If the LD50 is mistated, then correct it indicating your reason in the edit summary. Just restrain yourself. In terms of the amount of research on its toxicity, my guess is that the toxicity has been investigated pretty heavily, but that no amount of research would satisfy those convinced of conspiracies. The record shows that there is nothing very special about fluoride or most of its anionic derivatives, good or bad. It's actually rather boring, but then again, I am a sulfur guy and we think we have the niftiest element. --Smokefoot (talk) 12:48, 10 October 2011 (UTC)

What? Are you against history?!

So you didn't like my history of lubricants! I mean, it was awesome! :) Hey, you need to start somewhere. Don't you like Romans?!

Ha ha, anyway. I reread the categorization I made for oil additives, and I think that the way I broke down the different types of additives will greatly enhance a reader's understanding of the topic. It is one of those edits that makes people say, "Ah, ha, so this is not an arbitrary list of junk written by kids. This is an article that explains the topic in a logical way." It really shows you how a simple re-organization can make more sense than a rewrite if you do it right. Strangely enough, the list follows a rough chronological order for the oil industry, or at least an order that goes from the simple to the complex. E.g. soot control is a hot topic of the 2000s, while VI improvers and "viscocity breakdown" are more of the 1980s. The other thing to note is that the detailed and exhaustive list in this section is supposed to contrast the random additives found in Dura Lube, which are more marketing and less functional in their properties. I like to saw logs! (talk) 05:57, 15 October 2011 (UTC)

New Page Patrol survey

New page patrol – Survey Invitation Hello Smokefoot! The WMF is currently developing new tools to make new page patrolling much easier. Whether you  have patrolled many pages or only a few, we now need to  know about your experience. The survey takes only 6 minutes, and the information you provide will not be shared with third parties other than to assist us in analyzing the results of the survey; the WMF will not use the information to identify you. If this invitation  also appears on other accounts you  may  have, please complete the  survey  once only.  If this has been sent to you in error and you have never patrolled new pages, please ignore it. Please click HERE to take part. Many thanks in advance for providing this essential feedback. You are receiving this invitation because you  have patrolled new pages. For more information, please see NPP Survey. Global message delivery 13:20, 26 October 2011 (UTC)

Re: Expansion of Kumada Coupling

Hello Smokefoot. I've been working on my edits for the Kumada coupling article and currently have a rough draft. I definitely plan on expanding some aspects (more figures, more detailed scope). If you'd like to read it to make sure it is appropriate for Wikipedia, you can find it in my sandbox. I would definitely appreciate any feedback! Bear in mind, that this is for a class assignment, but I do want to make the article as useful and relevant as possible. Thanks! Jonathan.Raybin (talk) 17:28, 31 October 2011 (UTC)

DOTA especially for lanthanides?

Hi! Do you know any more applications for DOTA-lanthanide-complexes besides gadoteric acid? None of the other ions mentioned in DOTA (chelator) is a lanthanid. Thanks --ἀνυπόδητος (talk) 16:06, 30 October 2011 (UTC)

Well Gadoteric acid is a train-wreck for a medical-pharmaceutical audience (who dont need to know the real chemistry). I found a lot of information on DOTA as a chelator for ions other than lanthanides. So I will try to help with DOTA (chelator). One tricky part with all of these polyaminocarboxylates is that the degree of protonation before and after complexation, which is often vaguely described. Even the ligands are complicated. DOTA (chelator) is not really labeled correctly at least to an coordination chemist. We struggle with this issue at EDTA. In Wikipedia, DOTA is used as a loose jargon for both the tetraanionic conjugate base and the free acid (H₄DOTA). If we spend too much time describing these details, we will fatally encumber the article and lose the audience. --Smokefoot (talk) 17:14, 30 October 2011 (UTC)

I think it's fine to cover the acid and the anion together (but then I'm not a coordination chemist), and I agree that long intricate descriptions would reduce readability. I am having problems with the exact structures as well; I've been drawing the yttrium complex with the carboxylates pointing outwards (as in the sources), but I'm beginning to suspect it looks more like the gadolinium one. On the other hand, we are one carboxylate short in structures like DOTATATE and 90Y-DOTA-biotin. --ἀνυπόδητος (talk) 18:09, 30 October 2011 (UTC)

Well, it looks like that basics are being communicated pretty well. Surprisingly active area that I barely knew about. One minor (probably) caveat with the structures is that the species that crystallise and are analyzed by crystallography are not necessarily the same as the solution species which is the active material. For 90Y-DOTA-biotin the structure should show the four O's bonded to Y also, according to my source (Coordination Chemistry Reviews of 2009). So not only the carboxylates, but the amide-oxygen centres as well so as to encase the metal in an N4O4 environment. Not sure about the water being a ligand. If drawing is a pain for you, let me know and I can help.--Smokefoot (talk) 18:57, 30 October 2011 (UTC)

I think it's easier for me to do it; I've got the raw BKchem file on my HD. Would you draw the bonds to the –O^–´s or the =O´s? (I'm aware of the mesomerism, but drawing something like this would probably be more confusing than helpful.) Can you tell whether File:90Y-DOTATOC.png, File:Y-90 tacatuzumab tetraxetan structure.svg and related structures also have got this configuration? --ἀνυπόδητος (talk) 08:36, 31 October 2011 (UTC)

For File:90Y-DOTATOC.png, I recommend simply removing the H's on the carboxylic acids and drawing dotted lines from these O centers (coordination chemists usually do not show charges on ligands, but you can) to the Y. You can also draw a similar dotted line from the 4th oxygen, the one on the amide that links to the peptide. If you try to get too faithful to the structure, the drawing is almost impossible, so simply showing connectivity would be fine. At least for me.--Smokefoot (talk) 12:14, 31 October 2011 (UTC)

 Done: File:90Y-DOTATOC complex.png. In case you know about the corresponding complexes with other ions, File:111In-DOTATOC.png, File:177Lu-DOTATOC.png and File:68Ga-DOTATOC.png also might need additional coordiantion bonds. By the way, DOTA (chelator) now states "The main applications involve the lanthanides and in such complexes DOTA functions as an octadentate ligand", while our only example of an octadentate complex is the one wth the transition metal Y. --ἀνυπόδητος (talk) 10:06, 1 November 2011 (UTC)

It's a terminology thing. DOTA and its derivatives almost always serve as octadentate ligands, but the complex could have any coordination number of 8 or greater. I will try to clarify. --Smokefoot (talk) 13:13, 1 November 2011 (UTC)

Lithopone

It is nice, that you tried to clean up the article on Lithopone. But don't you think you pruned too much information? Like the list of the physical properties? 217.115.249.152 (talk) 09:58, 15 November 2011 (UTC)

Possibly. I couldnt understand much to the information that I deleted "Brilliant white and fine texture which is advantage over white lead and can be mixed with sulfur". And things like that. My guess is that the material that was deleted was pasted in from a label or a technical brief. But it would be great to upgrade this article using some good sources, and I would be glad to help. Thanks for the note.--Smokefoot (talk) 13:44, 15 November 2011 (UTC)

File:H4T.png listed for deletion

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re:SCl4

Maybe de:Schwefeltetrachlorid has some more references.--Makecat (talk) 10:46, 25 November 2011 (UTC)

Your nomination for deletion of – Shangyuchem

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All files in category Unclassified Chemical Structures listed for deletion

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Delivered by MessageDeliveryBot on behalf of MGA73 (talk) at 18:22, 28 November 2011 (UTC).

Thanks for fluorine work (some chem questions)

Saw several great edits and I saw you are the real deal as a chemist. The article is still evolving but getting there. I am going to fact-check the entire thing in a few days. Several places needing a ref will get fixed concurrently with that 'brary dive. And some content tweaks or better explanations to laymen (from learning the topic better).

1. What is hypoconjugation of fluoride? I googled that (even google scholar) and came up empty. Kept asking me for hyperconjugation, but even that seemed different from your point. Could we just say formation of bifluoride? (Of course that still leaves the question why it does not form in glacial acetic acid. Like what IS the role of the water?) Can you explain whole thing to me (in little words) or maybe send me off to a good ref? I do have Cotton Adv Inorg at home (not there, right now). I know the ref I had before was a website, but it was actually written by the author of a college chemistry textbook so I figured it would be decent...but you don't like it?

It should be homoconjugation (I forget my big words too!). It means that the acidity of HF depends on its concentration, unlike most acids. Concentrated HF is much stronger acid than is dilute HF owing to this equilibrium: 2 HF --> H⁺ + HF₂^-

1.5 "They are generally very strong and are almost always solvated, containing protonated ether or protonated water." I'm almost there on this one, but could you explain it a bit more on this talk page? How does what you mention here compare to H2SO4 or HNO3 or the like? Are they solvated in water (what is "solvate")?

2. ECF is a good add. I did not know of it. Is it the method used for production of Freon and Teflon (precursors) and PFOS and the like? Is it basically the whole organofluorine industry or just perfluoroalkanes?

I am no super-expert, but my strong impression is that it is only used to make perfluorinated things like PFOS. The preparation of C2F4 is on tetrafluoroethylene, I forget it now but it is slightly indirect. The routes to the various CFCs are on the CFC page I think, usually reactions involve HF + a chlorocarbon to eliminate HCl and give a chlorofluorocarbon.

3. "Illustrative of the complications in this area, fluoroantimonic acid consists, depending on the method of isolation..." I feel like we've added a complication (nature of the molecule versus the formula unit) and taken away the explanation of "why it is so strong". And not sufficiently explained the complication added. I know the superacids are a little funky and I'm not trying to be wrong, but I'm worried that we are not really supplying most important info (why strong) and replacing with something that only an in the field chemist would understand. Can you explain the point a little more on this talk page (will help me get the "so what" of the complications)? Maybe if we are glossing over too much on the superacids to the point of being wrong, we should add a few more sentences to explain how they really function. That will take care of your concerns that we are conveying bad info, but also unpackage the topic enough for someone who is a chemical engineer or a doctor or the like to get insights.

People love talking about fluoroantimonic acid, but the stuff itself is rather mysterious. So this topic is one where you get sucked into complicated explanations (i.e. in effect there is no "HSbF6"). The same goes for the more useful but less spectacular fluoroacids (as the article calls them, never heard that term) - HBF4 and HPF6. I agree with the gist of what you are getting at, why are they such strong acids. Because the anions are weakly basic. Why are the anions so weakly basic, because they are symmetrical and contain many electronegative centers (fluorides).

4. I am looking for more high level chemical info (structure trends, properties, preparations) on medicinal fluorides. We have a pretty decent section within "Biological roles". I might bring some of that down (perhaps the thing on stabilizing rings). Obviously, I don't want to just duplicate info amongst sections. Am making "Chemistry of the compounds" the place for the more technical chemical discussions. But for instance are peptides fluorinated or just these ring molecule thingies? 2-3 key insights like that and I can build a para and they are high level enough to be giving some overview.

User:Shootbamboo and I wrote a good section in organofluorine compounds that summarizes this area. But neither of us is v good at medicinal chem - for that we ask User:Edgar181

Another option could be just to cut the 2-3 drugs (not sure if we count the ether) out of the ribbon of organofluorines picture and move it up to biological roles. Hmm...

5. I am looking for a killer quote about the number of organofluorines. "More than a million documented" or whatever. The exact number is not important, but I want to use it in a topic sentence at the start of the section and just give the non-chemist reader some feel for the breadth of the topic. "Diverse" is too handwavey. I think a chemist groks that there would be a gazillion of them, since there are...a gazillion organic compounds, but I want something to help the layman.

Off the top of my head, the interesting aspect of medicinally important fluorides is that they are so numerous (starting with Prozac) because, apparently, the C-F bond is highly robust.

TCO (talk) 16:41, 28 December 2011 (UTC)

P.s. I may tweak a few minor things you wrote (e.g. center versus centre).

You are welcome (indeed encouraged) to slash and burn to produce a good article. I am not that uptight - you are doing a terrific job (and on ReF₆). The details on the extremely exotic fluorides of the synthetic elements seems a little esoteric for such an article. The compounds section is usually illustrative with no attempt to be even close to comprehensive. I will check back later when I have some time. Good luck.--Smokefoot (talk) 17:41, 28 December 2011 (UTC)

Thank you for kind words. That gives me enough to go on and I can get these things upgraded (info on prep methods particularly nice new info). Awesome.

I'll look at some books on the superacid strongness and HF weakness and see if there is an easy way to explain something insightful and also technically correct. If not, we may just simplify by omitting the rationales or put in a note or something. (Leaving current version for now.)

I'll tighten "Chemical properties" at the front. Want that accessible and small, agreed. Has been shaved some already. One option is to move some of the einsteinium details (binary compounds) down to "Compounds" section at the end. Just say all except helium and neon at top and mention the violence of the reactions. [Think I will do that.]

"Compounds" is pretty big, agreed. Is why I put at the end ("penalty box") and sectioned a lot. (Along with being more technical and less of a natural narrative.) We could end up spinning that out. I would prefer to wait until close to the end of the process to make that call.

TCO (talk) 18:16, 28 December 2011 (UTC)