Wikipedia:WikiProject Chemicals/archive05

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Archived discussion of WT:Chem in 2008

Contents

[edit] Diesel/Petroleum fuels

I'm not an active Chemistry project member but was wondering if any of the following articles are within the scope of your project (if not, where else they could/should be): Diesel, Biodiesel, Liquefied petroleum gas, Ethanol fuel. SheffGruff (talk) 18:36, 20 December 2007 (UTC)

  • They're correctly attributed to the Energy wikiproject. I added the {{chemistry}} with ratings to Diesel and LPG. Wim van Dorst (talk) 01:05, 8 January 2008 (UTC).

[edit] Lead(II) nitrate, back to FA?

Hi, all, I've copy-edited the lead(II) nitrate article from the Chemicals wikiproject, after it was recentely demoted from its FA-status. Would interested WP:Chem editors please be so kind as to provide feedback in its now running FA re-candidacy? Wim van Dorst (talk) 19:18, 31 December 2007 (UTC).

  • The FAC process for lead(II) nitrate has progressed well, with supporting starting to outbalance opposition. Please be invited to cast your votes now too, preferably positive, of course. Wim van Dorst (talk) 22:13, 14 January 2008 (UTC).

[edit] Multiple symbols for a single unit

As part of the discussion of the possible FA status of the lead(II) nitrate article, the question of the 'correct' symbol for the litre came up. According to SI policy, both 'L' and 'l' (and thus mL and ml, etc) are accepted, and both are used on wikipedia. As I understand it, the 'l' usage is common in Europe, whilst Australia, Canada, the US, and others favour 'L'. I am wondering whether some consensus usage would be helpful. I don't think we need different usages on different pages - or worse, on a single page. Thoughts? EdChem (talk) 13:54, 7 January 2008 (UTC)

  • I vote for upper case "L" simply because it is distinguishable from the numeral "1" when a sans-serif font is used. That said, I don't think we should go on a witchhunt to find and replace all instances of one with the other because there are really, better things to do on wikipedia. Either ml or mL should be consistent within the page, and that is enough. Similar arguments for the variant of English used. --Rifleman 82 (talk) 14:32, 7 January 2008 (UTC)
  • I agree with R on mL, purely on font considerations. Consistency within an article is the important issue. Axiosaurus (talk) 15:18, 7 January 2008 (UTC)
  • Totally disagree: in the old world Europe, it has always been lowercase 'l'. The uppercase 'L' alternative is only SI-allowed for some years, and definitely should not be the only designating symbol for 'litre'. If anything, we should formally denounce the use of either in our articles and use m3 (with formal SI-standard prefixes where appropriate). That should them be part of the Wikipedia:WikiProject Chemicals/Style guidelines. And I do agree with EdChem on the consistent use on a single page, whichever the choice. Wim van Dorst (talk) 01:01, 8 January 2008 (UTC).
    • I disagree with Wim because I believe Wikipedia is descriptive, not prescriptive. The truth is that liters and variants are commonly used by chemists, and we should not ban the use these units on philosophical grounds. --Rifleman 82 (talk) 03:12, 8 January 2008 (UTC)
  • I agree with Rifleman also. The capital one has been a formally accepted alternative by SI since 1979. And I disagree with m3 and related "cubic-length volume" units (unless one is emphasizing the unit equivalence as part of some math, obviously). I think it makes an already technical realm of WP too technical for no real gain in understanding. In a practical sense, volume-measuring devices are usually marked in direct volume units, no reason to obfuscate the issue for lay audiences, and someone who cares about precise cubic-length terminology already knows enough to convert it. DMacks (talk) —Preceding comment was added at 05:56, 8 January 2008 (UTC)

So, what is now the conclusion? It is clear that we will not prescribe the use of only m3 and dm3. But do I understand that we will allow consistent use within one article of (US spelling) the 'L' for liter, and (GB spelling) the 'l' or the 'L' for litre? Anyone going to write that up in the styleguides? Wim van Dorst (talk) 19:51, 8 January 2008 (UTC).

I can remember having a vociferous argument with a French professor almost exactly 10 years ago on this very issue (Michel, if you're reading this, you know who you are!). The litre is defined as one cubic decimetre: it has two possible symbols, l or L Bureau International des Poids et Mesures (2006). The International System of Units (SI) (8th Edn). ISBN 92-822-2213-6. p. 124.. I agree that we should be consistent within a given article, but I don't see what authority we have to impose one over the other (or to impose the dm3 over either of them). Physchim62 (talk) 20:30, 9 January 2008 (UTC)
What is the ACS Style Guide recommendation here, and what about similar style guides from other such organizations? Since we're making a (somewhat) arbitrary (though rationalizeable) style-guide decision here, would be useful to consider what other such guides suggest. DMacks (talk) 23:39, 9 January 2008 (UTC)

[edit] Good news - fact checking of chemboxes, etc

User:ChemSpiderMan (aka Antony Williams) has very kindly taken on an absolutely mammoth task - he is checking every single chemical substance chembox for accuracy. Although he is remarkably fast at this, it still involves MANUALLY checking every IUPAC name and structure, as well as generating an InChI and InChiKey for each one. Last I heard he'd spent over 36 hours of hard slog on this! His plan is then to link to Wikipedia from each relevant substance entry on his ChemSpider website. Obviously this is great news for us all round, but there are a couple of things we will need to do:

  1. Take a look at his PDF file listing possible problems, and leave comments here. Some refer to drugboxes - I have contacted the Pharmacology folks who write those. I have limited time right now, so I certainly can't fix them all myself, though I'll try to get to some ASAP. Some require us to reach a consensus. If anyone has time to help me work on these, please do, and post comments at User:Walkerma/Sandbox.
  2. We need to decide how to use this file and all the information contained in it. Should we get a bot to read the file and add in the InChIs and InChIKeys into all of the articles? If so, we need to decide if the InChIKey should be placed in the chembox or hidden as with the InChI (NB: I think InChIKeys are limited to 26 characters)
  3. There is a wider interest in the chemistry community for using Wikipedia chemistry pages, especially the chemical substance pages, to provide data for databases. See this recent talk page entry and this blog entry.

I'd like us to hold an IRC meeting next week to discuss some of this - would this be OK? Please comment below if you have any thoughts. Walkerma (talk) 04:01, 8 January 2008 (UTC)


That's great. Would be happy to help. IRC is fine. I'm available most weeknights 9-12 my time (1700-2000 GMT). --Rifleman 82 (talk) 04:32, 8 January 2008 (UTC)


ChemSpiderMan says: It's actually well over 120 hours of work so far. I estimate the total work will be around 300 hours, maybe more. The second PDF file is simply an update to the first file so you can junk the first PDF file. I actually made some edits on WP already from the initial list. Some of the edits are names but there are also incorrect structures as will become evident. The latest PDF file is on the ChemSpider site for anyone to read. I will keep updating on an ongoing basis. I'm up for attending an IRC discussion on this - I am just over 1/2 way through the files I have about 3800 records left...not all will be structures..there is no way to check except to open the record link.
What I'd like to discuss at the end of my project is a second level of curation. My intention is to produce an SDF file of structures and make it available to the WP:CHEM team for them to use. I am considering making the data freely available to everyone...a Wikipedia Structure file and it will therefore be possible to make Wikipedia structure and substructure searchable using other software tools. --ChemSpiderMan (talk) 05:00, 8 January 2008 (UTC)
The work that you are doing, Antony, is greatly appreciated. I've noted most of your comments and fixed many of the problems you have identified on article talk pages. If there are inconsistencies that have still not been addressed, feel free to note them here and someone will look into it, or let me know on my talk page and I'll do whatever I can to help fix it.
I really like the idea of a Wikipedia chemical structure file that would be substructure searchable. -- Ed (Edgar181) 23:03, 8 January 2008 (UTC)

Update of Wikipedia Review File I have updated the review file tonight and would welcome any feedback. Walkerma, you might want to upgrade your comments page with the new structures Details are available online here --ChemSpiderMan (talk) 12:40, 9 January 2008 (UTC) New update of project file available as of 1/15/2008 here --ChemSpiderMan (talk) 14:53, 15 January 2008 (UTC)

[edit] Dihydrogen hexachloroplatinic(IV) acid... or is it chloroplatinic acid?

Did a bit of copyediting here. I'll re-do the images eventually, but if someone else beats me to it... Question about the article name. Which should we use? I see the "chloroplatinic acid" more often. Any comments? Whatever we choose as the preferred, someone (I can) will have to edit the article to be consistent. Lastly, does anyone have easy access to this article?

R. T. Moravek, G. B. Kauffman and T. Mahmood (1967). "Nitrosyl Hexachloroplatinate(IV)". Inorganic Syntheses 9: 217-220. doi:10.1002/9780470132555.ch63. 

If this impurity is due to the action of the aqua regia, perhaps the section on "related compounds" can be rewritten into "production". --Rifleman 82 (talk) 16:33, 9 January 2008 (UTC)

It is certainly not "Dihydrogen hexachloroplatinic(IV) acid"! Hexachloroplatinic acid if you must. Physchim62 (talk) 20:09, 9 January 2008 (UTC)
Assuming you are going to end up with (H+)2 PtCl6-- then I believe the name should be Dihydrogen hexachloroplatinate(2-). I have confirmed this name in the naming software I have access to. --ChemSpiderMan (talk) 04:37, 10 January 2008 (UTC)
The renaming of sulfuric acid to dihydrogen sulfate might give a clue which name is the right one!--Stone (talk) 12:50, 10 January 2008 (UTC)

Hexachloroplatinic acid is the appropriate name for H2PtCl6. The PtCl62− ion would be called the hexachloroplatinate(IV) anion - the parentheses show the metal oxidation state rather than the overall charge (hence IV, not II-), and the "-ate" suffix indicates an anionic species. In the unlikely event that the anion HPtCl6− could be prepared, it would be named the hydrogenhexachloroplatinate(IV) anion. The name dihydrogen hexachloroplatinate(IV) would be used only if the pure substance were obtained as a molecular species or an ionic solid; when any such substance were dissolved in water and it dissociated or ionised, it should be referred to as hexachloroplatinic acid. The situation is similar to that for HCl - hydrogen chloride as an unionised molecule (usually as a gas), hydrochloric acid as an ionised aqueous solution. As for the chloroplatinic acid name, it may be used, but it is imprecise in my opinion, as it could be taken to refer to H2PtCl4. EdChem (talk) 14:22, 10 January 2008 (UTC)

Hexachloroplatinate(2-) is a perfectly correct name for the anion: note the difference in usage between Arabic and Roman numerals. The anion usually known as superoxide could also be referred to as dioxide(1–): it is impossible to assign an oxidation state to each of the oxygens. For the case in question, my preference is for hexachloroplatinic acid, which is unambiguous and easily recognised. Physchim62 (talk) 16:38, 10 January 2008 (UTC)

[edit] IRC discussion on using Wikipedia chemistry pages to provide chemical data

I'm proposing that we hold an IRC discussion this coming Tuesday. As you may have gleaned from recent postings, there is interest in using the Wikipedia chemical information, particularly information from Chemboxes, as the starting point for open access databases.

Background
How it may affect us
  • Curation (fact-checking) of data forcing us to clean up faulty or dubious data
  • Mashups with other websites, these could bring chemists from other sites onto Wikipedia
  • We may need to write a bot or reformat our data in order to make Wikipedia chemistry more accessible for the semantic web
Time

Tuesday, January 15th at 1900h 1600h UTC (11am US Eastern Time, 1700h Central European Time). Please note earlier time.

Location

Wikipedia chemistry IRC channel

Possible agenda items
  • What do we have? The dataset of chemical compounds, currently being cleaned up by ChemSpiderMan et al. - numbers, quality? Data in other chemistry articles, e.g. on chemists?
  • How can we make the data more easily searchable/mineable, and more suitable for the semantic web?
  • How can we foster mashups with other sites that might bring chemists to us, while providing useful chemical information for the other site?
Attendance

If you think you can attend, please sign up below. If you're not familiar with IRC, see this page and download simple software such as Chatzilla (for Firefox). User:Walkerma manages to use it, so it MUST be simple....!

  • I can make either time. Walkerma (talk) 20:18, 12 January 2008 (UTC)
  • I'll try. --Dirk Beetstra T C 20:50, 12 January 2008 (UTC)
  • I'm in. DMacks (talk) 22:03, 12 January 2008 (UTC)
  • I can attend. Also, in preparation for the meeting people might want to see the latest report that I have put online tonight here--ChemSpiderMan (talk) 01:22, 13 January 2008 (UTC)
  • I can attend at 1600 UTC, but probably not at 1900. --Itub (talk) 09:25, 13 January 2008 (UTC)
  • I will try to attend--Rzepa (talk) 14:00, 14 January 2008 (UTC)
  • I'll try. --Arcadian (talk) 06:27, 15 January 2008 (UTC)
Comment

Can we have it a bit earlier? By three hours — 1600 GMT/1100 Eastern US/1700 Central European/2400 Singapore? --Rifleman 82 (talk) 01:50, 13 January 2008 (UTC)

  • sigh*, I guess I could get up before noon on a vacation day if others prefer this time. DMacks (talk) 01:58, 13 January 2008 (UTC)
Oh dear! It's hard to fit everyone in, and I thought we'd covered everybody. I'm reluctant to switch things right now, just because I've been emailing people trying to find a convenient time, but I'll look into it. Are there any Californians, etc, who plan to attend? Walkerma (talk) 04:55, 13 January 2008 (UTC)
I must confess, that also fits better with me (19:00 is about dinner time for me .., late afternoon like 16:00 would indeed generally fit better), but I see that these meetings are problematic in time. --Dirk Beetstra T C 11:41, 13 January 2008 (UTC)
I am flexible in my availability but not between 2:30 and 5pm EST. I need to set up an IRC Client. Chatzilla is conflicting with FireFox and will not install. I am trying mIRC but have not been able to connect to the channel. I welcome assistance. At present I get a message that the channel is temporarily unavailable but it has been in this state for a while.--ChemSpiderMan (talk) 15:00, 13 January 2008 (UTC)
Give [1] a try? I get lots of problems with my uni blocking IRC, which causes a variety of messages (couldn't contact server, and with no server, channel unavailable). DMacks (talk) 15:58, 13 January 2008 (UTC)
It seems that everyone I've heard from, including Peter Murray-Rust, prefers the earlier time, so we'll go with that. Walkerma (talk) 20:43, 14 January 2008 (UTC)
Available bandwidth willing, I shall try to be there :) Physchim62 (talk) 13:11, 15 January 2008 (UTC)

AN updated PDF of the curation project report is available as of 1/15/2008. Available here--ChemSpiderMan (talk) 14:52, 15 January 2008 (UTC) Example of WP entry under CML/RDF for discussion on IRC Exploring RDF and CML [[2]] Petermr (talk) 16:10, 15 January 2008 (UTC)

[edit] Contribution for the Style Guidelines: layout of chemical reactions

Hi all, recent edits pointed out that there is a lack of layout definition in the WP:Chem Style Guidelines. Aspects that we ought to define include:

  • wikilinking in formulae, used in-line and in reactions
  • indentation of reactions
  • use of (s)/(l)/(g) and ionic notiation

I think good:

H+(aq) + OH−(aq) → H2O(l)

I think not good:

H+(aq) + OH-(aq) → H2O(l)

Please comment. Wim van Dorst (talk) 20:44, 13 January 2008 (UTC).

  • My preference is for there not to be wikilinking in formulae or in equations - especially not when they are links like the O in OH− linking to an article on the substance oxygen, as such links are potentially confusing. I don't object to links for states, as such links are simply explanations for the abbreviations used in equations.
  • I believe that centring looks better than indenting for equations, but don't feel that strongly about which to use.
  • Including states in equations is simply good practice. As such, we may also need to note the potential use of (sol) for cases where the solvent is anon-aqueous. Note, however, that equations in organic chemistry will frequently omit states, often including the solvent below the reaction arrow. On that subject, is there an easy way to do this? On the lead(II) nitrate page, I included an equation for the dissociation on dissolution, and would have preferred to have an 'H2O' over the arrow, but don't know a convenient way of adding it.
  • By 'ionic notation', I think Wim van Dorst is asking about net ionic equations as opposed to neutral species equations, and I strongly favour net ionic equations on the grounds of chemical accuracy.
EdChem (talk) 21:28, 13 January 2008 (UTC)

Re style guide:

  • I oppose wikilinking atoms in formulae. Seems distracting, tedious, and pretentious, IMHO. When reading about lysergic acid, a reader does not seek a link to carbon. If the group decides that formulae should to be wikified, then I hope that we don't force this format onto every formula within an article.
  • indentation of reactions. This style helps me with readability. On a printed page, centering is nice, but for some reason, I prefer the simple indent in WE.
  • use of (s)/(l)/(g). Oppose strongly. My guess is that this notation comes from the days (about 50 centuries ago) when aqueous chemistry and qualitative analysis were emphasized. The style seems archaic. It requires knowledge that is often unavailable and implies restrictions that are usually irrelevant. Also, if I understand the convention, it implies a level of absolutism that is misleading, i.e. that PbCl2 is insoluble, whereas it is poorly soluble in water. And it implies that most chemistry is aqueous, which is untrue for large parts of the field. Yes, in the 1950's it was comforting to see the precipitation of PbCl2 indicated explicitly. We do not see this format in any modern journal or monograph. I also think that the style makes an already difficult topic (chemical reactions) more difficult because the reader must not only contend with the chemistry, but also the phases (which again are often not known or are misunderstood).
  • ionic notation. Seems harmless often, but I prefer NaCl, not Na+Cl-. The notation also seems archaic since it implicitly (to me at least) ignores ion-pairing.

It is healthy to have this discussion so that we can imput these recommendations into a style guide.--Smokefoot (talk) 22:42, 13 January 2008 (UTC)

I don't like wikilinking formulae either, especially as atoms. If some obscure compound were expressed in CHN formula, it might be justifible to wikilink the entire thing. See also discussion on mickey mouse structures. --Rifleman 82 (talk) 01:45, 14 January 2008 (UTC)
In formulating (!) my opinion, I tried to base my opinion on the likely reader of the article, and what area of chemistry is being discussed.
  • I think wikilinking atoms in formulae is generally a bad idea (and very bad in something like lysergic acid), though I think it could be useful in a handful of basic articles such as water (molecule) or carbon dioxide, where the typical reader may be unfamiliar with what the formulae represent. It is somewhat helpful in an article like sodium chloride, because Na is not obviously sodium to a 12 year old, whereas MgCl2 is perhaps easier to grasp. A more liberal option would be to link only from the lead paragraph, only in inorganic articles, where it says, "potassium phosphate has the formula...."; I could live with that. Wikilinking organic groups such as Ph is useful, because many beginning orgo students struggle with these, and they're not listed in the periodic table on the lab wall (while noting Physchim62's hatred of Me for methyl).
  • Wikilinking a complete formula (once) in an equation IS appropriate (IMHO), particularly when the article is likely to be read by someone at the high school level. A more advanced reader probably won't even notice that Na2SO4 links to the sodium sulfate article, but that could be very helpful to a beginner.
  • In aqueous reactions, particularly those involving gas evolution, precipitation, etc, including the state should be recommended, though not mandatory. Smokefoot is right for the research level, but millions of schoolkids around the world are still mixing silver nitrate with sodium chloride in water, and in articles like lead(II) nitrate they may find the little (s) helpful. It would look silly in an article like cobaltocene, though.
  • I recommend a single indent (:) before text based equations, but structure-based (graphical) equations look better centred, IMHO.
  • In an inorganic context, writing (say) sodium sulfate as Na2SO4 should be the norm, other than perhaps to point out (in a basic article) how it dissociates in water. However, there may be cases where the ionic representation is appropriate, for example in an organic context such as this. Obviously there are many occasions where net ionic equations etc are being used quite appropriately.
Walkerma (talk) 05:33, 14 January 2008 (UTC)
  • I would favor: - no atoms links, no use of s,l,g (agree with smokefoot, old fashioned). Importantly I favor indentation over central positioning ALSO when it involves graphics. V8rik (talk) 16:39, 14 January 2008 (UTC)
  • My preferences are: 1) indenting equations; 2) using ionic equations where the "neutral" equations would give the false impression that that the neutral "molecules" exist in solution (for example, using AgNO3 + KI -> AgI + KNO3 to describe an aqueous reaction); 3) not using s,l,g in general, although they can be used for emphasis in cases where phase transitions or precipitations are being discussed, or where necessary to define a thermochemical property clearly (for example, the enthalpy change from a combustion reaction is not the same if you end up with water vapor or with liquid water). 4) No wikilinks in formulas, although in a handful of basic articles they might be OK. I especially dislike "contiguous links" where different letters in a word or formula link to different articles, such as OH. Linking the whole formula to the relevant article might be OK in some cases, but it is probably better to give the name and link it instead of linking the formula. --Itub (talk) 17:34, 14 January 2008 (UTC)

To make a proposal for the Style Guidelines, how about (please copy-edit!):

Chemical reactions
Chemical reactions in articles should be properly balanced and correct. Formulae in the reactions should not be wikilinked (do that in the introductory text), nor should the atoms in the formulae be wikilinked. Reactions may be numbered for referencing in the text.

The use of phase indication (s), (l), (g) should only be used if emphasis on the phase transition in a reaction is intended. Generally, they should be avoided. If used, the first occurrence of the phase indication should be wikilinked.

Inorganic reactions and text reactions should be left-aligned, with one indent (wiki-markup ':'). Organic reactions are mostly presented in a graphical way, and treated as images, wrapping around text or centered.

The Bamberger rearrangement
The Bamberger rearrangement

Good examples:

H+(aq) + OH−(aq) → H2O(l)
Na2SO4 + H2SO4 ⇌ 2 NaHSO4
  1. Dissolving pure iron in a solution of iron(III) chloride

Fe(s) + 2 FeCl3(aq) → 3 FeCl2(aq)

  1. Dissolving iron ore in hydrochloric acid
    Fe3O4(s) + 8 HCl(aq) → FeCl2(aq) + 2 FeCl3(aq) + 4 H2O
  2. Upgrading the iron(II) chloride with chlorine
    2 FeCl2(aq) + Cl2(g) → 2 FeCl3(aq)


Bad examples:

H+(aq) + OH-(aq) → H2O(l)
Na2SO4(aq) + H2SO4(aq) ⇌ 2 NaHSO4(aq)

I generally agree with the comments above, as summarised by Itub. However, I would put in a word in favour of indications of phase in some cases. Details of phase abbreviations can be found at International Union of Pure and Applied Chemistry (1993). Quantities, Units and Symbols in Physical Chemistry (2nd Edn). Oxford: Blackwell Science. ISBN 0-632-03583-8. pp. 46–47. Electronic version. and at Cox, J. D. (1982). "Manual of Symbols and Terminology for Physicochemical Quantities and Units: Appendix IV—Notation for States and Processes, Siginificance of the Word "Standard" in Chemical Thermodynamics, and Remarks on Commonly Tabulated Forms of Thermodynamic Functions". Pure Appl. Chem. 54: 1239–50. 

As Itub points out, it is often important to quote a phase when dealing with thermochemical quantities, eg

Cl2 (g) + 2e– ⇌ 2Cl– (aq) ; E° = +1.3583 V
Cl2 (aq) + 2e– ⇌ 2Cl– (aq) ; E° = +1.4203 V
(Student exercise: calculate the solubility of chlorine in water!)

They are also useful when discussing aqueous chemistry. In particular, I very much prefer H+ (aq) to H3O+: the former is correct and unambiguous, the latter is false in virtually every case in which it is used. Similarly, many students who write [[Fe(H2O)6]]3+ would not know what colour this ion actually is! (needless to say, they were not using it in their reactions, they were using a mixture of species which can be represented as Fe3+ (aq)). The equation

Pb2+ (aq) + 2I– (aq) → PbI2 (s)

not only emphasises the precipitation of lead iodide but also the hydration (to an unknown degree) of Pb2+ and I–.

Finally, to reply to Martin, I have no objection to using "Me" for methyl in text formulae! I merely pointed out that we are being helpful to our German colleagues if we don't use it in graphic formulae: in return, they shouldn't use φ for phenyl :) (not that I ever seen that in graphics from dewiki). Physchim62 (talk) 14:16, 20 January 2008 (UTC)

I have some issues with the 'good examples' provided by Itub that have been written above, drawing on the potential for confusion when using neutral species equations instead of ionic equations, and when leaving out states. For example, the given equation

Na2SO4 + H2SO4 ⇌ 2 NaHSO4

In an aqueous solution, I would suggest that a more appropriate equation would be:

SO42−(aq) + H+(aq) ⇌ HSO4−

or maybe:

SO42−(aq) + H3O+(aq) ⇌ HSO4− + H2O(l)

or perhaps, if one were using conc. sulfuric acid:

SO42−(aq) + H2SO4(l) ⇌ 2 HSO4−

but in such a case the equilibrium symbol is questionable, as the strength of sulfuric acid mandates a completion of this reaction. I am having trouble imagining a circumstance in which I might use the original equation as written. If the example was changed to something like sodium carbonate and citric acid (H3cit, for convenience), then a neutral species equation would be appropriate if grinding solids together:

Na2CO3(s) + 2 H3cit(s) → 2 NaH2cit(s) + CO2(g) + H2O(l)

but in aqueous solution, I'd use something like:

CO32−(aq) + 2 H3cit(aq) → 2 H2cit−(aq) + CO2(g) + H2O(l)

Such equations require states to be meaningful, and I would argue that neutral species equations without states for simple general chemistry processes are appropriate only for stoichiometric calculations - and the omission of states is often necessary in such cases because no reasonable and meaningful set of states can be applied.

Another example was:

  1. Dissolving pure iron in a solution of iron(III) chloride
    Fe(s) + 2 FeCl3(aq) → 3 FeCl2(aq)

where I would prefer a net ionic equation such as:

Fe(s) + 2 Fe3+(aq) → 3 Fe2+(aq)

Quite possibly E° = +1.21 V should also be appended, allowing the equation to illustrate why adding iron solid to an iron(II) solution will prevent the formation of substantial amounts of iron(III).

Adding spectator ions to equations can also introduce unneeded complexity. For example, suppose I were to add potassium permanganate solution, acidified with sulfuric acid, to a solution of iron(II) chloride. The net ionic equation allows the actual transformation to be seen clearly, emphasising the oxidation of iron(II):

5 Fe2+(aq) + MnO4−(aq) + 8 H+(aq) → 5 Fe3+(aq) + Mn2+(aq) + 4 H2O(l)

Now, to make a neutral species equation, I have to add 10 chloride ions, a potassium ion, and 4 sulfate ions. This immediately raises questions as to the other products. For example, which of the following options is 'correct'?

5 FeCl2(aq) + KMnO4(aq) + 4 H2SO4(aq) → 4 Fe(SO4)Cl(aq) + FeCl3(aq) + MnCl2(aq) + KCl(aq) + 4 H2O(l)
5 FeCl2(aq) + KMnO4(aq) + 4 H2SO4(aq) → Fe2(SO4)3(aq) + 3 FeCl3(aq) + MnSO4(aq) + KCl(aq) + 4 H2O(l)
5 FeCl2(aq) + KMnO4(aq) + 4 H2SO4(aq) → Fe(SO4)Cl(aq) + 2 FeCl3(aq) + Fe2(SO4)3(aq) + MnCl2(aq) + KCl(aq) + 4 H2O(l)
10 FeCl2(aq) + 2 KMnO4(aq) + 8 H2SO4(aq) → Fe(SO4)Cl(aq) + 5 FeCl3(aq) + 2 Fe2(SO4)3(aq) + 2 MnCl2(aq) + K2SO4(aq) + 8 H2O(l)
10 FeCl2(aq) + 2 KMnO4(aq) + 8 H2SO4(aq) → 6 FeCl3(aq) + 2 Fe2(SO4)3(aq) + MnCl2(aq) + MnSO4(aq) + K2SO4(aq) + 8 H2O(l)
10 FeCl2(aq) + 2 KMnO4(aq) + 8 H2SO4(aq) → 2 Fe(SO4)Cl(aq) + 6 FeCl3(aq) + Fe2(SO4)3(aq) + 2 MnSO4(aq) + K2SO4(aq) + 8 H2O(l)

I can argue for any of them, I suppose, but they are raising an issue that is chemically not relevant - since all of these soluble ionic products are dissociated in solution, trying to decide which spectator anions are 'paired' with which spectator cations is pointless.

Basically, states are needed because processes like:

Na2CO3(s) + 2 H+(aq) → 2 Na+(aq) + CO2(g) + H2O(l)

and:

CO32−(aq) + 2 H+(aq) → CO2(g) + H2O(l)

are different processes, and yet both could have the same neutral species equation:

Na2CO3 + 2 HCl → 2 NaCl + CO2 + H2O

and it is only this neutral species form that is appropriately stateless.

By the way, sorry for the length - I expected this to be shorter when I started typing! EdChem (talk) 11:03, 23 January 2008 (UTC)

Note: I didn't write those "good examples"! I think it was Wimvandorst. I'll comment on the specific points later. --Itub (talk) 11:54, 23 January 2008 (UTC)
Sorry, Itub, I appreciate your point. I am not looking to get into any criticism of people, and I have struck out your name. I am trying to comment on what might be included in general style guidelines, and am hoping that the use of appropriate net ionic equations (with states) be adopted for simple chemistry topics. EdChem (talk) 12:07, 23 January 2008 (UTC)
I once again oppose indicating states in the manner recommended by EdChem. We do not allow this format in journals, and few modern textbooks adopt it. This "fundamentalist" gesture would condemn WE-chem to appear old-fashioned or "mickey mouse," a trumping of the recommendations (above) by those that have considerable expertise on core content (vs format). We decided a long time ago that we were not going to demand "ethanoic acid," again despite the wailings of certain fundamentalists. I recommend that we drop this squabble about insisting (and resisting, in my case) states and get back to our main job: contributing excellent content. None of the monomethyl pyridines have their own pages!! We don't have a page on coordinative unsaturation! Readers are seeking overviews on biofuels, lignocellulose, and bioenergy.... There's more important work to do!--Smokefoot (talk) 15:01, 23 January 2008 (UTC)
I would like to let the editor decide which form of chemical reaction (s)he applies in a certain article, e.g., the dissolution of iron in a ferric chloride solution, as part of the production process of ferric chloride, is in my perception best shown as:
Fe(s) + 2 FeCl3(aq) &rarr 3 FeCl2(aq)
That is because a reader then can visualize the overall production process: a huge vessel filled with an dark brown watery solution, and bars of iron are dropped in it. And I seem to recall that iron does 'dissolve' much better in ferric chloride solution than in (e.g.) ferric nitrate or ferric sulfate.
As an alternative, if I would be describing the intricacies of the oxidation states of iron, I'd be using:
Fe0 + 2 Fe3+ → 3 Fe2+
And if the article would need to point out something like iron dissolution, one may use yet another reaction:
Fe(s) + 2 Fe3+(aq) → 3 Fe2+(aq)
So, the context defines the most appropriate reaction to be used. The styleguide now only shows (which ever reaction chosen) how to display it, viz., without wikilinking atoms or compounds, indented (not centred), etc. That's a nice step in the good direction for me. Up to the next FA: WP:Chem really needs a new one this year ;-). Wim van Dorst (talk) 21:26, 23 January 2008 (UTC).

[edit] {{Chembox new}}

I've done a final sweep using chem-awb (talk · contribs) of the remaining articles transcluding {{Chembox header}} but not {{Chembox new}}. There are 89 remaining which require substantial handcoding. See [3] Further discussion should be at Wikipedia talk:Chemical infobox. Help is appreciated! --Rifleman 82 (talk) 02:13, 14 January 2008 (UTC)

I have replaced the chem box on sulfate with chem box new. Originally I had removed it but this change was reverted. A brief scan of other ions/functional groups shows that using chem box in this way is unusual. However I can see why a summary box is useful. but using chem box seems to be overkill, and maybe confusing if later we link through it to other databases. Any thoughts? Axiosaurus (talk) 10:54, 19 January 2008 (UTC)
It is indeed unusual, I think I would remove the chembox there, though we could discuss having a specialised box for 'functional groups' .. --Dirk Beetstra T C 11:22, 19 January 2008 (UTC)

I was thinking of writing a style guide to functional groups, but I guess it's been pre-empted by this. I'm recovering from severe computer difficulties, but I will be able to get on it in by this weekend. I'll be counting on you guys for comments and feedback! --Rifleman 82 (talk) 12:47, 19 January 2008 (UTC)

  • I would favour a new box- and yes I guess we should discuss this on the Chemistry page, but ensure we publicise any discussion here Axiosaurus (talk) 20:09, 19 January 2008 (UTC)

[edit] Linking CAS Numbers out from Chem and DrugBoxes

For those on the IRC Chat yesterday you will recall my concerns about linking out to other online services using CAS numbers to "search" databases. I believe it is a potentially daangerous practice. A single "compound/structure" can be associated with multiple CAS numbers. But a single CAS number should be associated with a single substance. So, having a CAS number associated with multiple compounds (neutral compound, chloride salt, bromide salt OR same connection table with multiple stereochemistries - absolute, partially defined, undefined) is not good in my mind. I might agree that linking the CAS number to ONE record in an external database, where that link is to the correct "structure representation" (i.e. that exact one given in the CAS registry) is correct. For sure we will not be doing these links INTO the CAS registry as we will not be given permission to do that gratis.

Example: 1) Fructose-1-phosphate: if you click on the CAS number you see THREE structures - only the second matches the structure shown in the ChemBox. This is not a direct link therefore ..it's a search. Now, additional structures might be added to the external site and associated with that CAS number by accident so the problem could get bigger. 2)Taxol. Presently ChemBox links out to MeSH. So, there are inconsistencies regarding WHERE CAS numbers link to. I would prefer MeSH if anywhere but there is actually little value at that page but it does lead you here. MeSH is HIGHLY curated, but not necessarily perfect. Using this CAS number as a search gives three hits in PubChem, seven hits in eMolecules and one hit on ChemSPider. Please note...this is NOT for any other reason other than the fact that the data for Taxol have been manually curated by me. There are MANY examples of multiple structures on ChemSPider with the same CAS number. The multiple Taxol structures are there because of differences in stereo.

I've opened the discussion...comments?--ChemSpiderMan (talk) 15:22, 16 January 2008 (UTC)

Please take into account here, that we are linking to eMolecules as a linkfarm to get more information, it is indeed a search. The other side of this medal could be the old situation, where there were sometimes extensive lists of external links in the external links section, providing links to several suppliers. That is something that certainly should be avoided.
I just found that also pubchem (for the above example of Fructose-1-phosphate) gives more than one result: pubchem (5 structures). Taxol contains a {{drugbox}}, so that links to another site, which is more 'drug-oriented', which explains the other link.
I have started a workshop on {{chembox new}} (first) to get a bit of line in certain aspects of the box. See Wikipedia:Chemical infobox/Workshop. Maybe that is a good place to have a discussion on 'what could link where' as well? Cheers. --Dirk Beetstra T C 16:55, 16 January 2008 (UTC)


[edit] Request to edit/provide feedback on ChemSpider article

As a result of ChemSpiderman (me) posting a link to an article regarding ChemSpider today EdJohnston approached me with a suggestion to update the article on Wikipedia. I have suggested some text but would prefer that someone else review/edit/comment/curate and post appropriate data representing the site rather than have it come from me. I welcome guidance and suggestions. My suggested text is here. In conversation with Ed today it turns out that there might be a perception that ChemSpider (because it is still a beta) is not a "working site". It presently has over 2000 people per day using the site for searching and has spiked at 3000. It is "labeled a beta" because I am not ready to name it as non-beta yet. It does not mean it's not used and does not mean it isn't providing value. It's been the basis of the majority of curation work I have done on Wikipedia which I do believe is of value. Comments welcomed.--ChemSpiderMan (talk) 22:41, 17 January 2008 (UTC)

[edit] Weekly IRC meetings for WP:CHEMISTRY/WP:CHEM

We had an IRC meeting on Jan 15, 2008 to discuss validation of chembox information and reuse of the data in databases and mashups. We agreed to meet again informally one week later (today, Jan 22) to discuss some of the details, like how to structure the data, how to deal with salts, etc. It looks like this will become a regular meeting, so we have set up a page at Wikipedia:WikiProject_Chemistry/IRC_discussions. Please join us on January 29 at 1600h UTC (11am US EST, 1700h Central European Time)! We hope to discuss InChIs and InChIKeys, though it will depend somewhat on who is able to come to the meeting. Cheers, Walkerma (talk) 18:41, 22 January 2008 (UTC)

[edit] Validation of CAS numbers in chemboxes - please help

ChemSpiderMan has recently been doing validation work on our chembox data, but he can't do CAS nos. For this reason we will be doing this ourselves over the coming weeks/months, so please try and help out if you can. We could presumably also be adding CAS nos. for those pages that lack them. The work page for this is at Wikipedia:WikiProject Chemistry/CAS validation.

Some questions:

  1. Is there some way for us to integrate the resultant information into the pre-existing page, List of CAS numbers by chemical compound?
  2. Should we create redirects for CAS nos. - where those don't currently exist - or should we rely on the search capability to find the article from a CAS# search?
  3. This list is only organics, at some point we'll have to be looking at inorganics as well.
  4. Can anyone draft a student in to help?

I'm guessing that a bot or AWB could do the first two tasks fairly easily, though I don't know. Walkerma (talk) 20:44, 22 January 2008 (UTC)

I could easily write a script to do the first one, does not need a bot-account (I can copy-paste the result in the end). Generating the second is more difficult, I would need a bot-account for that, I can see if User:Rifleman_82 can run perl-scripts (he should be able to on his linux-box). I guess I would pull the information from the transclusions of {{chembox new}}, which would result in a full list, including inorganics. --Dirk Beetstra T C 21:55, 22 January 2008 (UTC)
I have no problem going back through inorganics in the future but note that my project intention is to make Wikipedia structure/substructure searchable and in many cases the inorganics don't have structures. Rather, they have formulae. Let me finish the "organics" first...it's a big enough project...then we discuss what has been learned by this project and go after inorganics and organometallics.--ChemSpiderMan (talk) 03:28, 23 January 2008 (UTC)
Please also note that many compounds have multiple CAS numbers. Especially amines and organic acids have different CAS numbers for all their salts. It might be a good idea to list all of them. Сасусlе 04:44, 23 January 2008 (UTC)
This was part of the IRC Chat today...my belief is that the ChemBox should be "self-consistent". The structure, IUPAC name, CAS number, SMILES should all refer to the same structure. IF there is a decision to list all CAS numbers then they need to be annotated..for example (chloride salt, bromide salt etc). Personally I think this should either be an additional component of the ChemBox or not present at all. The ChemBox should be preserved to describe the chemical/substance being displayed/discussed and not represent multiple compounds. --ChemSpiderMan (talk) 05:12, 23 January 2008 (UTC)
I am working through the chembox new list and sorting the inorganics. The problem ones, and there aren't that many, have the same issues --e.g. (i) multiple compound "versions" described in the chembox typically hydrates; (ii) some compounds e.g.gold(IV) bromide that have 2 CAS numbers etc etc. I will be interested to see what comes out of the organics push. Definitely the area to focus on, after all Wiki is short of content on organometallics and transition metal complexes and clusters. Its not even hot on basic inorganic! --Axiosaurus (talk) 19:22, 24 January 2008 (UTC)
Axiosaurus..you might be aware of the validation exercise I have undertaken on chemical "structures" on Wikipedia? I am willing to take on the same on inorganics but am more interested in doing organometallics next in reality. I would like to support both on ChemSpider...and do to a certain extent...but would want to work with someone on Wikipedia to clarify inorganic and organometallic structures. I assume you might be interested. if so, please initiate a conversation on my Talk Page. Thanks--ChemSpiderMan (talk) 20:27, 24 January 2008 (UTC)

[edit] New articles

Phenidone, Uragan D2, α-Santalol, 2-Heptanone and Imidazolidinyl urea every one might have a look.--Stone (talk) 08:45, 24 January 2008 (UTC)

Stone..I've checked the ChemBoxes when available. The Imidazolinyl Urea article was a problem. Check the history and you will see what I tried to do with the Name...the best name is with the N',N italicized but, try as I might, I cannot get this into the box: N',N-methylenebis{1-[3-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]urea}. Maybe there is a trick I am yet to learn for this. Can you insert the IUPAC Name above into the box?--ChemSpiderMan (talk) 13:33, 24 January 2008 (UTC)
I just noticed theat Media-wiki is interpreting the primes...it should be N-prime, N-triple prime —Preceding unsigned comment added by ChemSpiderMan (talk • contribs) 13:35, 24 January 2008 (UTC)
I replaced the characters by unicode prime characters, which are different from the normal "single quote" characters. For the triple prime I used three prime characters; there is also a "triple prime" character but it doesn't look to good on my computer... --Itub (talk) 13:43, 24 January 2008 (UTC)
Another option if you want to use normal quotes is to use <nowiki>''</nowiki>. --Itub (talk) 13:45, 24 January 2008 (UTC)

Another new article, I just started DMPU (1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone), shoot it if you want. --Dirk Beetstra T C 11:57, 25 January 2008 (UTC)

Comments added to the article. I have already added the structure into the curation set I am working on.--ChemSpiderMan (talk) 15:34, 25 January 2008 (UTC)

[edit] Diagrams

I noticed that the picure on the Terephthalic acid (benzene-1,4-dicarboxylic acid) page the image of the skeletal structure of the formula contained the Kerkulé structure of the benzene molecule, should this not be a ring in the centre instead of the 3 double bonds for accuracy? The image: -- Joestephens (talk) 23:35, 24 January 2008 (UTC)

That is a standard way of drawing phenyl rings in a skeletal formula - the aromaticity is implied. -- Ed (Edgar181) 23:39, 24 January 2008 (UTC)
I have seen only 3-5 structures on Wikipedia with the ring drawn inside the cycle and I would suggest they are removed and replaced with the alternating single/double display. I will make a note of them during my curation efforts as I see them.--ChemSpiderMan (talk) 23:53, 24 January 2008 (UTC)

[edit] IRC discussion on handling InChIs

We will be holding our next IRC meeting on Tuesday, January 29th at 1600h UTC. We want to decide how best to handle InChIs. I have posted a "request for comments" on the CINF listserve, so we can find out how people use information like SMILES and InChI on Wikipedia. Please join us at the IRC meeting! Walkerma (talk) 09:09, 26 January 2008 (UTC)

I have posted the responses to my questions here. There are nine sets of specific answers, and two other responses that are less specific to my questions (but still helpful). Please take a look before the IRC meeting if you can. Walkerma (talk) 05:03, 29 January 2008 (UTC)

[edit] Functional groups style guidelines

I'm trying to prepare a style guide for functional groups. This would include articles like alkane, alcohol, aldehyde, etc. Of particular interest (to me, at least), is the spectroscopy section - how do we identify and characterize these compounds?

I've prepared a skeleton here. Please take a look and expand/comment! --Rifleman 82 (talk) 10:13, 28 January 2008 (UTC)

[edit] Malathion

Hello all - while not officially part of the chemical project, I've been working on the malathion article for a little bit now, and it's page that apparently falls into your scope. When I initially came across it, it's POV was quite biased towards anti-pesticide views (references were quoted which were taken out of context, exagerated... etc). I did my best to clean it up, but I am worried that with prime mosquito season coming up in much of north america over the next few months, it could become the target of anti-pesticide groups again. This worries me, as there is a large debate in my hometown over the use of malathion (one of the few cites who still sprays with it), and I know many people look to Wikipedia as there source of info, especially since the Wiki page is the number one google hit for malathion. I myself don't have lot's of time to monitor the page, as I'm a medical student, and will be in northern Canada without internet access for several of the upcoming months. If I could get a little help monitoring the page for deviations from a neutral POV, that would be wonderful.--corvus.ag (talk) 15:57, 7 April 2008 (UTC)

[edit] Link pointing to compound rather than reaction removed. Are you sure?

User: ChemGardener removed "link pointing to compound rather than reaction":"[Cuneane|Metal-ion-catalyzed σ-bond rearrangement]" from Rearrangement reaction and from List of organic reactions. Are you sure that it was right correction? May be only one example of this reaction type is better than nothing? (Before somebody will write an article "Metal-ion-catalyzed σ-bond rearrangement".)--Tim32 (talk) 12:14, 29 January 2008 (UTC)

I would say that linking to the molecule is OK as long as the link is presented clearly. [Cuneane|Metal-ion-catalyzed σ-bond rearrangement] is misleading because the reader will expect a link to a reaction and instead gets an article about a molecule. I say just link it with the phrase: "Metal-ion-catalyzed σ-bond rearrangement, such as the rearrangement of cubane to cuneane". --Itub (talk) 13:02, 29 January 2008 (UTC)

May be Metal-ion-catalyzed σ-bond rearrangement: cubane to cuneane? Ok?--Tim32 (talk) 22:12, 29 January 2008 (UTC)

I took it out because of it seemed to be misleading. It would be fine to have some way of listing it in List of organic reactions, possibly as a red link to encourage creation, rather than as a pointer to the Cuneane article. There are other examples in the list where the article hasn't been created yet. One possibility would be: Metal-ion-catalyzed σ-bond rearrangement - such as Cubane to Cuneane. This would encourage creation of it and suggest inclusion of the Cuneane synthesis.
I would not put it in Rearrangement reaction as a red link or any type of link. I don't think it qualifies as a key rearrangement reaction at this point. - ChemGardener (talk) 19:18, 30 January 2008 (UTC)

Please, see I wrote metal-ion-catalyzed σ-bond rearrangement, but the problem still to be open for other reactions! I think, current WikiProject Chemicals community is unable to write single article for every reaction type.--Tim32 (talk) 16:56, 10 February 2008 (UTC)

Nice to see an article on this fascinating and large topic. As it currently stands, the article is barely a placeholder. So my recommendation is to shore up the science (and redraw the images uniformly and well) rather than worrying about linking. The title seems too cumbersome, which limits the article's impact.--Smokefoot (talk) 17:22, 10 February 2008 (UTC)

Thanks for nice! About "redraw the images": the images made by ChemSketch (free chemical structure drawing package that includes input and output in InCHI format) -- see, International Chemical Identifier#Software and services and please, compare with the images from Michael B. Smith, Jerry March, March’s Advanced Organic Chemistry, 5 th Ed., John Wiley & Sons, Inc., 2001, p. 1459. My images look better;) --Tim32 (talk) 19:16, 10 February 2008 (UTC)

[edit] Indexing of compounds

Sorry that I couldn't join you on IRC last night. However, on reading the discussion it seems that the problem of external access could be solved relatively easily by compiling indices of WP chem articles (as ChemSpiderMan and others have already done for personal use) and publishing them under a suitable licence. That way the "primary key", as far as WP is concerned, would become the name of the WP article and InChIs, CAS numbers etc would become secondary keys. This might seem like an awful lot of work (and it will be, doubtless), but it can be automated, both through {{chembox new}} and {{InChI}}.

The benefit would be that anyone could download and use the indexes in their products; our responsability, as it is now, would be to add data to pages which is as accurate as possible. What do people think? Physchim62 (talk) 19:26, 30 January 2008 (UTC)

I'm very intrigued by this, but I also don't properly understand your idea. Can you elaborate a little? Walkerma (talk) 05:44, 31 January 2008 (UTC)

The idea would be to run the search on a database dump to come up with a list such as:

7784-34-1|Arsenic trichloride
7732-18-5|Water (molecule)

which associates the identifier with a wikipedia article title (or URL). The indexes would be published, and could be used by anyone wishing to perform a search on one of those identifiers but not trusting Google or the MediaWiki search. Indexes can already be complied for {{Persondata}} (see Wikipedia:Persondata), the format on which {{InChI}} is based. Physchim62 (talk) 11:00, 3 February 2008 (UTC)

[edit] Test of automated article selection

Only rarely do I wear my WP:1.0 hat on this page, but I'd like to ask a favour. We have been testing a bot for selecting articles for offline release based on quality and importance assessments. We want an offline release of around 20,000-30,000 articles from all subject areas, and we want these to be picked based on a combination of importance and quality. Importance is considered more important than quality (we don't just want a collection including lots of FAs and GAs on trivia then find we failed to include Battle of Stalingrad, Spain or (heaven forbid!) organic chemistry. However, an FA like lead(II) nitrate would probably be included, because although it's not a really important topic, it is clearly non-trivial, and a very nice article.

We have a tentative selection of WP:Chem articles. A couple of comments: First, the hitranking is very rough, but should get much better. Second, there will be some articles that aren't on the list.

The articles are ranked in order of Score3; the three score options are based on a balanced combination of quality and importance. I'd really like to know if people think this would be an appropriate ordering of the articles, and if it would be a reasonable selection if we picked (say) all articles with Score3 >900 (or >800?). If the ordering is wrong, how have we got it wrong? Please comment! Thanks, Walkerma (talk) 06:21, 31 January 2008 (UTC)

After looking at the list, I would say that articles above 1200 are clearly very important. Below 1200 it is more of a mix, which starts to include comparatively obscure chemicals that presumably got in due to high article quality (which is not necessarily a bad thing!). The main issue I noticed is that some articles got in while others were excluded due to accidents of wikiproject classification. For example, we have chlorine, but not hydrogen, oxygen, nitrogen, or carbon. All of them are important, but apparently only chlorine is listed as a WP:Chemicals article while the others belong to WP:Elements. Similarly, some drugs, biomolecules, and polymers got in that are perhaps not as important as "chemicals" but are clearly important in their own categories. For example, paracetamol (but no aspirin?), vitamin K (but not vitamin C?), and polyester (but no polyethylene?). Finally, a few chemicals that come to mind that I think are important but missing from the list are the following (perhaps you can check what their rankings are and why): sodium carbonate (or sodium bicarbonate), calcium oxide (or calcium hydroxide), acetone, ethyl ether, and methanol. --Itub (talk) 12:05, 31 January 2008 (UTC)
Yes, there are definitely "must-have" articles like methanol that didn't make even it onto the list - if they did, I'm sure they'd have a high score. Our next list will be more complete, and have more accurate hit rankings (e.g. AlCl3 gets far more than the # indicated). As for elements, they are ALL in fact already on all our general releases, but the bot will pick them up through the Elements wikiproject. That chlorine is on our list is really an anomaly (though I accept that elements are chemicals too!). You're right about the less important ones, but we opted to make quality a factor too, as we have room for the occasional thing like Raney nickel. Thanks a lot for your excellent input! Walkerma (talk) 15:40, 31 January 2008 (UTC)

[edit] Redirect for N2O-N?

Hi! I was looking up some information on various greenhouse gases, and was pleased to see that somebody has put in redirects for most of the formulas I was looking for. However, I repeatedly came across mention of "N2O-N" in discussion of wastewater and soil, but couldn't find out much about it. Surely the main problem is that after 20 years my chemistry knowledge has faded greatly. But if somebody could put in a redirect to the proper name, I'd be much obliged. Thanks, William Pietri (talk) 08:00, 31 January 2008 (UTC)

N2O-N is N2O. The exact meaning of -N is not clear from the publications, but has a meaning within the greenhous gas community.--Stone (talk) 09:40, 31 January 2008 (UTC)
I found this book that says it means "N2O measured in nitrogen units": [4]. For example, 1 pound N2O-N = 1.57 pounds N2O (because N2O is only about 63.6% N). --Itub (talk) 12:23, 31 January 2008 (UTC)
Fabulous! That eases my mind greatly. I was interpreting it as somehow having an extra nitrogen molecule along for the ride, and couldn't make heads or tails of the numbers from there.
After your explanation, the next thing I wondered was why people would do this. A pal tells me that often you'll know the quantity of something before a reaction. E.g., if you have a ton of coal, you know you'd have n kilos of carbon. After burning, you assume you'd have n kg CO2-C, or 44/12x kg CO2. Still seems a little wonky to me, but I'm sure many things in my profession would seem equally wonky to outsiders.
So thanks! I'll leave it to you guys to figure out whether this info has any place in Wikipedia, as I'm way out of my depth. William Pietri (talk) 21:41, 31 January 2008 (UTC)
You are right this nomenclature of the strange atmospheric chemists has to have a place somewhere!--Stone (talk) 22:02, 31 January 2008 (UTC)
It's actually quite a common way of expessing analytical results, although it's the first time I've seen it used for nitrous oxide. Physchim62 (talk) 14:09, 1 February 2008 (UTC)

[edit] Indigo dye

I put up a Chembox new onto the page of Indigo dye, but it is little bit short and the two possible CAS numbers 482-89-3 or 12626-73-2 are also not the standart I wanted to have. So I left it hiding untill somebody is able to help.--Stone (talk) 09:31, 31 January 2008 (UTC)

According to NIST, the first of these CAS numbers is the correct one, while the second refers to the isomer where the two carbonyl groups are cis to one another. I have edited the article accordingly. Physchim62 (talk) 16:05, 31 January 2008 (UTC)

[edit] two lead(II) oxide articles

There are two articles lead(II) oxide and lead (II) oxide for PbO. The former is much the better article and reflects a lot of concerted editing. Can someone with the power/knowledge delete the lead (II) oxide article please.--Axiosaurus (talk) 16:53, 2 February 2008 (UTC)

Thanks RM--Axiosaurus (talk) 17:42, 5 February 2008 (UTC)

[edit] Some renaming of articles

We have an article tin dioxide which should probably properly be called Tin(IV) oxide.
There is an article red lead which should be probably be called Lead(II,IV) oxide, with red lead becoming a redirect.
With the compound PbCO3 we have an interesting(?) situation;lead(II) carbonate redirects to cerussite; we have a separate article for white lead,an alternative name PbCO3; lead carbonate links to cerussite. I guess we should really have a chemistry page for lead(II) carbonate, a mineral page for cerussite, and make white lead and lead carbonate redirects to lead(II) carbonate. Opinions anyone? If needed I am happy to do the lead(II) carbonate article if that is what is agreed. --Axiosaurus (talk) 17:41, 5 February 2008 (UTC)

Why is tin(IV) oxide preferred over tin dioxide for SnO2?
Ben (talk) 19:07, 10 February 2008 (UTC)
I too vote for tin dioxide over tin(IV) oxide (and for titanium dioxide over titanium(IV) oxide, and for acetic acid over ethanoic acid, etc., etc.) Yikes. Now Axiosaurus's questions about red lead and the minerals are more complicated issues ... Suggestions are also sought for an improved name for the article with the unfortunate name Metal-ion-catalyzed σ-bond rearrangement (hmm... maybe we need "proton-induced conversion of amines to ammonium cations") --Smokefoot (talk) 19:22, 10 February 2008 (UTC)
I've redirected lead(II) carbonate to lead carbonate, and I have moved white lead to lead carbonate over the redirect. I hope that solves the problem. --Rifleman 82 (talk) 19:27, 10 February 2008 (UTC)
About Metal-ion-catalyzed σ-bond rearrangement: this name has been gotten from the book "Michael B. Smith, Jerry March, March’s Advanced Organic Chemistry, 5 th Ed., John Wiley & Sons, Inc., 2001, p. 1459." Another name (such as "proton-induced ...") may be WP:NOR problem...--Tim32 (talk) 20:07, 10 February 2008 (UTC)
Well I'm a little surprised guys --looks like the convention for IUPAC naming of compound articles ha staken a knock. I don't mind myself--I'm very old and prefer the good old names! thanks for the lead carbonate redirects -RM I'll put PbCO3 on the to do list. (Note use of {{chem|Pb||C||O|3}}. I've not used this new to me template before--does anybody else?)--Axiosaurus (talk) 10:10, 12 February 2008 (UTC)

[edit] Rosocyanine

The article has been tagged to be split since 2006. I think that a decision should be taken whether to split or not soon. -- 217.11.34.119 (talk) 22:39, 9 February 2008 (UTC)

I created a stub for rubrocurcumin. Unfortunately, I did not find the CAS number and other properties. --Leyo 20:30, 26 February 2008 (UTC)
I added in CAS#, formula, and mass. -- Ed (Edgar181) 20:53, 26 February 2008 (UTC)
Great. Where did you find the CAS#? It's not included in PubChem and other databases I tried. Can you also check if the CAS# 37204-72-1 for rosocyanine is correct? Thanks in advance. --Leyo 21:15, 26 February 2008 (UTC)
I get CAS numbers directly from CAS using SciFinder. 37204-72-1 is correct for rosocyanine. -- Ed (Edgar181) 21:27, 26 February 2008 (UTC)
Unfortunately, I don't have access to SciFinder. I have now changed Rosocyanine to a single-substance article as it was suggested. --Leyo 00:30, 27 February 2008 (UTC)

[edit] InChIKey resolver

Folks here may be interested in a very lively discussion on the ChemSpider blog here. It's a long post, with loads of replies, but very interesting. Here's the gist:

  • InChIKeys are very handy things for structure searches on the web. They can allow you to do (in effect) a structure search on the web!
  • However, if you find an InChIKey separated from a structure, you can't convert it to a structure or even an InChI - the hash only works one way. This can be a problem if you do a search like this and find a hit like this which has simply a list of InChIKeys and a set of structures. Which is which?
  • Wouldn't it be nice if we could resolve these, just like we can with a DOI?
  • An InChIKey can (in effect) be resolved using a lookup table, as used here. But what if it's not in ChemSpider? There needs to be a more comprehensive system for resolving these.
  • How should such a system be organised - one central location or in a "federal" system? Where should/would such a system be located - PubChem? CAS? IUPAC? ChemSpider?
  • Antony (aka (User:ChemSpiderMan) is considering making this his next big thing to work on.

I think a lot of the issues raised here are useful as we try to coalesce our ideas on structural representation on Wikipedia. Walkerma (talk) 19:13, 12 February 2008 (UTC)

[edit] Pseudohalogen Names

Cyanogen chloride, Cyanogen bromide, Iodine cyanide should get consistent names.--Stone (talk) 19:43, 12 February 2008 (UTC)

  • Which? As I read the IUPAC names in the articles, they aren't consistent. But what about cyanic chloride, cyanic bromide and cyanic iodide? Wim van Dorst (talk) 22:08, 12 February 2008 (UTC).
If I had a clue I would have done it, but with this inorganic stuff! Iodcyan was my guess, but in the wrong language.But with all possible redirects I would start.--Stone (talk) 22:52, 12 February 2008 (UTC)
Is this one of these electronegativity issues like we see with oxygen difluoride vs. dichlorine monoxide? I know that ClCN and BrCN are commonly named as cyanogen halides, and the halide is the electronegative part. A Google search gives both names for ICN, but I'm pretty sure the CN is the more electronegative part of the pseudohalogen. In my perusings I also stumbled across another related stub called cyanogen halide. I'd like to get the view of an inorganic chemist on this (Smokefoot? Axiosaurus?) Walkerma (talk) 04:35, 14 February 2008 (UTC)
My personal experience of using or sourcing any of these compounds is zero so no help there. I do not even know what the official IUPAC name is -- their documents are very legal and rather dense - and so am I. My vote, for what it is worth, is for the cyanogen halide name - purely on my impression that it is more common for suppliers , recent patents and papers. (Wiberg, Greenwood and Cotton all very carefully sit on the fence on this - giving both names) Consistency is the key - we are in good company- whatever we do. As long as the non chosen name is first in the other names list and is mentioned in the lede. After all guys you voted for tin dioxide rather than tin(IV) oxide!--Axiosaurus (talk) 18:51, 14 February 2008 (UTC)

[edit] Classes of chemicals

I was simply wondering if pages could be made for classes of chemicals that were all chemically similar, such as C3O2, C4O2, and C5O2, which I also happened to notice was not in this project. I'm not exactly sure what this class of chemicals is called, as I'm somewhat new to chemistry, and if there are pages for classes of chemicals, I would like to create this one, whatever it is called.--IdiotsOpposite (talk) 00:57, 13 February 2008 (UTC)

I would call the class "carbon suboxides". We do have an article on the first compound, which is called carbon suboxide. Perhaps the others can be added to that article as well, unless there is enough information to have separate articles for each. --Itub (talk) 07:58, 13 February 2008 (UTC)
not every chemical deserves its own page, take for example a look at boronic acid or xylene V8rik (talk) 19:51, 13 February 2008 (UTC)
Thanks for the info guys, and thanks also to Smokefoot, who posted in my talk page about this question. I'm also going to start work on the stub article β-carotene, and since it started first, it takes preference. However, I might make a section in the carbon suboxide article after I work on β-carotene. I make no guarantees, but I'll try to do what I can.--IdiotsOpposite (talk) 23:09, 13 February 2008 (UTC)
Well, replying again with comments and questions. I've worked a little on the carbon suboxide molecule. I skipped β-carotene after I saw that it was listed under "biochemistry", not "chemicals". I mainly added things in the chembox and a small amount of content change. However, I noticed that carbon suboxide is not in the worklist. I don't have a problem with that, but why is carbon suboxide within the scope of WikiProject Chemicals and yet not in it's worklist? I think that it should be added. —Preceding unsigned comment added by IdiotsOpposite (talk • contribs) 00:41, 14 February 2008 (UTC)
Thanks for joining us and helping out! The worklist contains a collection of around 380 articles that we targeted, in order to ensure we had a good, representative selection of major topics covered. There are actually something like 5000-7000 articles on chemicals in total (though many aren't tagged as yet) - that bigger list is here. It certainly doesn't mean that these other compounds don't matter, the worklist was just to provide some focus. The suboxides article would be a useful addition. Thanks! Walkerma (talk) 02:04, 14 February 2008 (UTC)
  • There are two wikiprojects relevant here: Chemistry and Chemicals. Of course they closely work together and effectively editors work on articles out of both interest scopes. Typically I rate real chemical compounds against Chemicals and groups or classes of chemical compounds against Chemistry, same as I would rate articles for discoverers of chemicals or important reactions of chemicals. In the basic, the WP:Chem is to provide a huge dictionary with chemical (and physical) details of chemical compounds. All interesting Chemistry topics are being discussed in other wikiproject (e.g. Elements) or in the mother wikiproject of Chemistry.
  • The worklist, dating from 2005(!), was the start of the Wikiproject Chemicals, generally known as WP:Chem, allowing us to get a fair coverage of all chemical compounds in the world with at least a serious number of representing chemicals. This list has been fixed since Summer 2006, so unless there is a serious omission in the setup of the list, I would propose to stick to it.
  • All that does still mean: please be welcome to work on any article you would like, either in the WP:Chem (worklist or not), or in the Chemistry wikiproject. Any contribution towards a better coverage of the whole wide field of Chemistry, including elements, chemicals and other sub-wikiprojects, is a Good ThingTM. Wim van Dorst (talk) 16:11, 17 February 2008 (UTC).

[edit] Amiloride

The structure provided on the amiloride page is wrong. It should have four primary amine groups, but each is shown as simply an N atom at the end of a single bond. I have no idea about uploading graphics (haven't explored that yet, and don't have time to do so now). So, would someone please ChemDraw (or whatever) a corrected structure and upload a replacement image? Thanks, EdChem (talk) 15:01, 14 February 2008 (UTC)
The structure on the Esmolol page is even worse, BTW. EdChem (talk) 15:19, 14 February 2008 (UTC)

Fixed, with Edgar181's help. --Rifleman 82 (talk) 15:38, 14 February 2008 (UTC)
Looks like we were doing the same thing at the same time. I was trying to figure out what the problem with esmolol was, before realizing you had already uploaded a fixed version. :) -- Ed (Edgar181) —Preceding comment was added at 15:43, 14 February 2008 (UTC)
Thanks to you both. :) EdChem (talk) 15:46, 14 February 2008 (UTC)
Just a reminder, there are lots more that still need fixing. And glucose is another complete mess we need to fix soon, see these comments. The battle goes on! Cheers! Walkerma (talk) 17:39, 14 February 2008 (UTC)
I am the creator of Image:Amiloride structure.svg (now fixed), and just wanted to say I'm always willing to fix any errors found in my SVGs. Or even make new ones from scratch. Just drop a note on my talk :-) ›mysid (☎∆) 19:52, 14 February 2008 (UTC)

[edit] Laboratory synthesis

Is there a rule not to keep (too detailed) sections on laboratory synthesis? If not this old edit should be reverted. Thanks. --Leyo 20:09, 19 February 2008 (UTC)

Well, Wikipedia is not an instruction manual, so I would think it isn't a lab manual either. That's something that's bothered me about SPSS also. Would be good to establish an explicit guideline in the chemistry realm, since some processes, reactions, conditions, etc are relevant and important content in their own right. DMacks (talk) 20:18, 19 February 2008 (UTC)
In de-WP (my home WP), we have a directive on this topic. According to it, we do not allow such detailed descriptions of synthesis like the example above. --Leyo 00:51, 20 February 2008 (UTC)
To me the Laboratory synthesis of HBr section is permissible and it should be reinstated. It would be a manual if the text would go like dissolve 10 grams of A in 100 ml of B and stir for 1 hour at 34 degrees etc. V8rik (talk) 21:16, 19 February 2008 (UTC)
On a related topic, I like the approach that laboratory syntheses are described separately from the industrial routes, but I think that the latter should be emphasized when possible.--Smokefoot (talk) 23:38, 19 February 2008 (UTC)

I've re-added the section (BTW, I never think twice about undoing unexplained deletions of entire sections by IP users!). There's nothing wrong with mentioning methods of synthesis and giving a few chemical equations. As V8rik says, this is not like a lab manual at all; a manual (or the experimental section of a paper) would be step-by-step and give specific amounts, times, conditions, equipment, and details such as methods of stirring and separation. --Itub (talk) 05:18, 20 February 2008 (UTC) I just looked at the peptide synthesis article and that one is a perfect example of manual-like writing which goes against policy. --Itub (talk) 05:24, 20 February 2008 (UTC)

I just added a paragraph about this to the style guide.[5] How does that look? --Itub (talk) 10:32, 20 February 2008 (UTC)

Looks great. --Rifleman 82 (talk) 14:15, 20 February 2008 (UTC)

[edit] Butylene

This article isomers of butylene is out of harmony with the text, which mostly uses butene. I would like to rename it as just Butene and expand its contents which are quite thin atm--AssegaiAli (talk) 16:15, 23 February 2008 (UTC)

Wikipedia's style is to name articles with the most frequently used name, and for chemicals this generally has meant preferring common names over systematic/IUPAC names. The current title of the article "Isomers of butylene" is unecessarily cumbersome, and has no advantage over either "butene" or "butylene", so I would certainly favor a name change in that case. It doesn't matter too much to me whether it ends up at butene or butylene, but I think it would be a good idea to have consistent naming of the series ethene/ethylene, propene/propylene, butene/butylene, etc. As far as I know, the only one that has been discussed extensively is ethylene. Consensus in that case was to stay at "ethylene" because it is by far the more commonly used name, even though "ethene" is the systematic name. -- Ed (Edgar181) 20:42, 23 February 2008 (UTC)

[edit] Diisopropyl fluorophosphate

Could an admin move diisopropylfluorophosphate to diisopropyl fluorophosphate? The latter would be in line with the salt nomenclature typically used for esters, e.g. triethyl phosphate.

I tried make the move myself, but was foiled by the redirect at diisopropyl fluorophosphate.

Ben (talk) 20:03, 1 March 2008 (UTC)

I'll point you to WP:RM, which handles these sorts of things. Best, shoy 22:54, 1 March 2008 (UTC)
Erm, it's been done hours ago. --Rifleman 82 (talk) 04:58, 2 March 2008 (UTC)

[edit] X-Pro

Before I nominate it for AfD, perhaps somebody would like to save this confusing redirect/disambig/stub. --Piotr Konieczny aka Prokonsul Piotrus| talk 15:52, 3 March 2008 (UTC)

Ah, I speedied it. WP is not a dictionary/directory/whatever; at this point we should concentrate on "real" articles. --Rifleman 82 (talk) 16:01, 3 March 2008 (UTC)

[edit] adding IUPAC 2005 names to organometallics

I have made a start checking through organometallic IUPAC names and checking them against the 2005 IUPAC inorganic recommendations (full text of the red book is 4.13MB pdf @ http://www.iupac.org/publications/books/author/connelly.html).
Before I get going in earnest I'd appreciate opinions on the best looking version of the name. The example is diiron nonacarbonyl and the issue is the appearance of the dashes used as separators in the name. (The chembox in the aricle shows my first effort and the problem)

1. tri-μ-carbonyl-bis(tricarbonyliron)(Fe-Fe) all dashes using the keyboard minus key "-"

2. tri−μ−carbonyl−bis(tricarbonyliron)(Fe−Fe) all dashes using the "&minus"

3. tri—μ—carbonyl—bis(tricarbonyliron)(Fe—Fe) all dashes using the long dash selected in the wiki editor i.e below the preview window

Personally I prefer a mixture of &minus for the literal portion and long dash for the metal metal bond suffix i.e.

tri−μ−carbonyl−bis(tricarbonyliron)(Fe—Fe)

I only have Firefox and IE7 so how do these look in other browsers? --Axiosaurus (talk) 20:41, 5 March 2008 (UTC)

Why would you use a minus sign instead of a hyphen? They do not mean the same and have different usage conventions. As far as I know, chemical names normally use hyphens, but bonds in text (for example, when you say "Fe–Fe" bond) use en dashes. If you can, look at the ACS style guide which has a lot of good (IMO) recommendations about use of hyphens, en dashes, em dashes, an minus signs. --Itub (talk) 05:56, 6 March 2008 (UTC)
I always use en dashes when "describing" bonds (e.g. in an image title), as Itub suggests. Fvasconcellos (t·c) 15:41, 8 March 2008 (UTC)

[edit] Which apostrophe?

Hey everybody, I am active in german wikipedia's Chemistry Project and recently I found an article using uncommon apostrophes in the title: de:8’-Apo-β-caroten-8’-al. So I asked myself, which kind of apostrophe should be used in names of chemical substances. I didn't find any answer yet, but perhaps you can help me. Thanks, --NEUROtiker (talk) 21:26, 5 March 2008 (UTC)

The symbol to be used should be a prime (') as in 1,1'-Bi-2-naphthol, not an apostrophe (’) as in de:8’-Apo-β-caroten-8’-al. In some fonts they may look the same though. -- Ed (Edgar181) 01:10, 6 March 2008 (UTC)
Thanks. Do you know any source which I could refer to? Some typographic or IUPAC guideline or similar? --NEUROtiker (talk) 23:29, 7 March 2008 (UTC)
That is what is recommended in the ACS Style Guide. But this may actually be much more complicated than I thought because different fonts depict those two symbols in different ways. For example, when I look at this page, the two symbols look the same - both are vertical lines. When I look at the text in the edit window, the prime is vertical and the apostrophe is slanted up to the right. On another computer I use, the prime is slanted and the apostrophe is curved. The depiction of the prime in the ACS Style Guide is slanted. -- Ed (Edgar181) 12:02, 11 March 2008 (UTC)
An interesting side-issue for WP: how does one bold or italicize it, given that the character is the same as the wiki-markup mark? For example, N,N'-dimethylformamide should have the "N" in italics (not sure about the prime mark), but "''N'',''N'''-dimethylformamide" is broken. What HTML or other entity code is this character? -- User:DMacks 15:32, 11 March 2008 (UTC)
I think you could use the code '&prime;' (actually typing this code without it being convertised is actually already an interesting task), this gives ′. --Beetstra (public) (Dirk BeetstraT C on public computers) 18:22, 11 March 2008 (UTC)
testing: N,N′-dimethylformamide .. works. --Beetstra (public) (Dirk BeetstraT C on public computers) 18:23, 11 March 2008 (UTC)
N,N′-dimethylformamide N,N′-dimethylformamide N,N′-dimethylformamide super! DMacks (talk) 19:45, 11 March 2008 (UTC)
Excpet that DMF has only one nitrogen, so it doesn't need a prime at all...  :) -- Ed (Edgar181) 19:54, 11 March 2008 (UTC)
Well yeah, it's a crappy example:) Maybe WP is smart enough to know "you're doing it wrong"? DMacks (talk) 19:56, 11 March 2008 (UTC)

[edit] Sodium lauryl sulfate has incorrect image

In looking at the image on sodium lauryl sulfate:

it appears to be missing the sodium atom at the right end. Please respond on Talk:Sodium lauryl sulfate#Incorrect image if I'm wrong (or right!) and feel free to fix the article. Cburnett (talk) 02:07, 7 March 2008 (UTC)

[edit] WikiChem

Folks, I have been watching the pain of dealing with CAS. Would anyone be interested in helping build a Wikimedia project that would be free to all and end our reliance on CAS? Geoff Plourde (talk) 22:00, 9 March 2008 (UTC)

Our reliance on CAS is minimal, and their attempts to restrict our use of CAS information are probably illegal. Physchim62 (talk) 12:39, 10 March 2008 (UTC)
I agree with PhysChim62 - there is no reliance on the CAS Numbers. There is value but no reliance. Articles would be valuable without the numbers but there is definitely additional value in having the numbers. If you would like to get involved in a project other than WP:Chem then you might want to connect with me offline. We are working on WiChempedia as discussed here. --ChemSpiderMan (talk) 00:29, 11 March 2008 (UTC)

[edit] CAS and Wikipedia

CAS, a division of the American Chemical Society, is pleased to announce that it will contribute to the Wikipedia project. CAS will work with Wikipedia to help provide accurate CAS Registry Numbers® for current substances listed in Wikiprojects-Chemicals section of the Wikipedia Chemistry Portal that are of widespread general public interest.

The CAS Registry is the world’s most comprehensive collection of chemical substances and the CAS Registry Number is the recognized global standard for chemical substance identification.

CAS views Wikipedia as an important societal tool for the general public, and this collaboration with Wikipedia is in line with CAS’ mission as a Division of the American Chemical Society.

We look forward to working with the Wikipedia volunteers over the next few weeks to make this happen.Eshively (talk) 13:44, 12 March 2008 (UTC)

[edit] Periodic acid

I've given it a chembox, somewhat arbitrarily choosing the solid dihydrate form (H5IO6) instead of HIO4 which the article states, exists in solution or after dehydration of the orthoperiodic acid. Take a look and comment, please? --Rifleman 82 (talk) 15:52, 15 March 2008 (UTC)

Perhaps phosphoric acid, which has ortho and meta forms, is relevant. --Rifleman 82 (talk) 15:56, 15 March 2008 (UTC)
Iodine acids form a series H5IO6, orthoperiodic acid; HIO4, periodic acid; HIO3, iodic acid; HIO2, iodous acid; HIO, hypoiodous acid. Funnily enough IUPAC 2005 allows these names as they are systematic. --Axiosaurus (talk) 17:34, 15 March 2008 (UTC)
I should have added that H5IO6, HIO4, HIO3 can be isolated as solids. Also in addition to the formally named acids there are some others I should have mentioned e.g. H7I3O14,"triperiodic acid" and H3IO5, "mesoperiodic acid" neither of which can be isolated; and HI3O8, "anhydro-iodic" acid a solid adduct of HIO3 and I2O5. --Axiosaurus (talk) 10:22, 16 March 2008 (UTC)
With all respect, Axiosaurus, are you sure about what you've written? The non-hydrated formula for iodic(VII) acid would be HIO4, but I regularly see it written as H5IO6: I am quite willing to believe the latter formula. The iodine atom is large and it would be normal to expect it to have octahedral coordination and not tetrahedral coordination: see, for example telluric acid. Physchim62 (talk) 16:21, 19 March 2008 (UTC)
Oh ye of little faith! Orthoperiodic acid,H5IO6, X-tal structure shows a straightforward monomeric complex of octahedral iodine with 1=O and 5 -OH groups. Solid HIO4 on the other hand has a chain, polymeric sructure (see Wiberg & Holleman) edge shared octahedral, I bridged by O atoms and non bridging O and OH groups. (this was new to me I must have missed that one somewhere along the way) Your instinct about octahedral was quite right. (However IO4− IS tetrahedral with a bond length of 178pm (see Greenwood)). The naming of these acids has been a bit patchy. Older books I have call them all "periodic acids" . 1966 cotton and wilkinson calls H5IO6 paraperiodic acid, and the IO4− ion metaperiodate, which tallies with Wiberg which gives metaperiodic as an alternative name for HIO4. HIO4 is difficult to prepare from what I can read - I shall try to follow up the original paper as I am intrigued. H5IO6 according to Wiberg can be used to prepare a variety of iodate, "periodate" salts depending on conditions e.g. salts containing the following IO4−, H4IO6−, H3IO62− H2IO63− and IO65−. Greenwood quotes some equilibrium constants for the various HnIOm species in aqueous solution.--Axiosaurus (talk) 19:34, 20 March 2008 (UTC)

[edit] Cesium hydride

This article is at AfD. It has recently been created and is really only one sentence. It should of course also be renamed to Caesium hydride. --Bduke (talk) 06:46, 21 March 2008 (UTC)

[edit] Element names and Aluminum

I'd like to formally request that this wikiproject note that the spelling of the element "aluminum / aluminium" be restricted to the international version only in chemical related articles, not generally throughout the encyclopedia.

An overzealous editor has just tried to apply this to the entirety of the engineering usage articles, including the rather ludicrous spelling change of the "Aluminum Association", the US trade group, to "Aluminium Association". This is just not appropriate or acceptable. The guideline has to be limited in scope to the reach that the name actually has. Georgewilliamherbert (talk) 19:14, 21 March 2008 (UTC)

If you'll look at my contributions, you'll see that I've restricted my spelling changes to articles that are chemistry-related. I think WP:ENGVAR takes precedence for other articles. I've been making a conscientious effort to apply the spelling changes only to where it is appropriate, such as not making changes to links, journal titles, etc. If among the thousands of spelling corrections, I have made an error, I apologize. You simply need to politely point out the mistake and I'll correct it. It's ridiculous to suggest rolling back all my changes. I think articles on alloys are clearly chemistry-related articles, but I can see that others might disagree. If you disagree, I'm willing to politely discuss it, if you are. Element16 (talk) —Preceding comment was added at 19:26, 21 March 2008 (UTC)

[edit] Caesium v cesium

Efforts to make the spelling of the element Caesium consistent has met with opposition by editors of Global positioning system on the grounds that a caesium clock is known as a cesium clock in the USA and as GPS was invented in the USA then WP:ENGVAR should take precedence over WP:SULF. I would welcome comments on the discussion page of Global positioning system. Thanks Velela (talk) 00:42, 22 March 2008 (UTC)

[edit] Shortcut

What about creating a shortcut for Wikipedia:WikiProject Chemistry/Structure drawing? I would have proposed WP:CSD, but it is already in use. --Leyo 15:55, 24 March 2008 (UTC)

What about WP:CSDG (Chemical Structure Drawing Guide)? 212.41.125.139 (talk) 02:50, 29 March 2008 (UTC)
Done. I also added WP:Chem/Structures. Physchim62 (talk) 14:02, 29 March 2008 (UTC)

[edit] Strem

Started a new article, do take a look: Strem Chemicals. --Rifleman 82 (talk) 15:34, 26 March 2008 (UTC)

Looks like a perfectly good stub to me, and the company is notable. However, you may want to add some independent sources preemptively, because short articles about companies are often nominated for deletion within hours by people who doubt the notability of the company. --Itub (talk) 15:42, 26 March 2008 (UTC)

[edit] MPTP IUPAC name

Most sources use the name "1-methyl 4-phenyl 1,2,3,6-tetrahydropyridine" for MPTP, but PubChem reports as IUPAC name computed from the structure "1-methyl-4-phenyl-3,6-dihydro-2H-pyridine". Is PubChem right and everyone else wrong, or is this a bug in PubChem's algorithm? AxelBoldt (talk) 14:25, 28 March 2008 (UTC)

Both appear to acceptable IUPAC names (if you add the necessary hyphens to the first one), although I prefer the PubChem version as it avoids the "1-hydro" in the other version: it isn't a hydrogen atom in the final structure, it's a methyl group, even if it starts out as a hydrogen in the "parent hydride" from which that name has been derived. The downside of the PubChem name is that most people are not familiar with the rules for "indicated hydrogen" which you need to know to make sense of the name. Physchim62 (talk) 16:37, 28 March 2008 (UTC)

[edit] Are skeletal formulae PD-ineligible?

A bot on Commons is converting the permission of every skeletal formula it can find to PD-chem (This image of a structural formula is ineligible for copyright and therefore in the public domain, because it consists entirely of information that is common property and contains no original authorship.).

Are skeletal formulae automatically in the public domain? There are often many different ways of drawing a skeletal formula, and the one chosen requires skill and judgement on the part of the author, to get maximum clarity. I know that the law on copyright varies greatly from country to country (Germany, for example, requires a lot of originality to make something copyrightable) - which law applies to the Commons - Florida law?

What about reaction schemes? And 3D images?

Ben (talk) 16:48, 31 March 2008 (UTC)

My feeling is that some skeletal formulae may not be eligible for copyright, but that many are. Therefore converting them all by bot without using judgement is a very bad idea. -- Ed (Edgar181) 16:54, 31 March 2008 (UTC)
Some formulae (methane, for example) are pretty certainly ineligible for copyright. However, that doesn't mean we should be saying that all formulae are. We've done very well so far with licensed chemical structures, and I have gone so far as to nominate the badly-worded (IMHO) copyright tag for deletion here. Physchim62 (talk) 17:28, 31 March 2008 (UTC)

[edit] Fulvalene

fulvalene or pentafulvalene. A microreviw doi:10.1002/ejoc.200500231 and a article [6] suggest, that this is pentafulvalene not fulvalene. And the first synthesis was done 1915doi:10.1002/cber.19150480136. So should we rename it or change the article to a article about all possible fulvalenes?--Stone (talk) 17:26, 7 April 2008 (UTC)

  • Synthesized by Matzner / Doering in 1958 but never published? What is going on here....V8rik (talk) 21:04, 7 April 2008 (UTC)