Wikipedia talk:WikiProject Chemistry/Archive 30

Here we go again with Plasmic Physics
Once again User:Plasmic Physics is editing chemistry articles. We has a respite of a few months. In my opinion, the edits are not just weird, often wrong, but they are hurtful to our readership. His edit to the radical cyclopentadienyl is found here: []. On the same day he changed acetic acid article to point out that the reactive group is the carbonyl, not the OH, see []. Can some administrator please try to negotiate terms with him again?--Smokefoot (talk) 00:32, 6 May 2014 (UTC)


 * Note that cyclopentadienyl (a term which readers would mainly find when running into organometallic terms, hence mostly denoting the anion) has over the course of time been rewritten from exactly that (the anion) to the free radical. The free radical is about the last thing a reader would look for, they may run into an organic moiety having a cyclopentadiene ring attached to it (already rather unique in comparison to the anion).  IMHO, this article should be strictly about the anion, its bonding to metals.  Mentions of the free radical or the organic group should be minimal (if notable at all).  Note: I have completely undone the rewrite, which is mainly if not completely by Plasmic Physics, which changed the article from the anion to the radical - it is now back at the anion-state).
 * I believe both should be covered, and leave it to those with interest to determine where. Encyclopedias cater to interest, but also lay out the landscape in intellectual areas, and so the radical species, as it exists in good secondary literature, should appear, however short the section might be. Le Prof  Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
 * I have reverted the acetic acid edit. The man in the street is familiar with acetic acid and its acidity, which stems from the OH, not from the C=O (one could argue from the COOH, I find it always dangerous to use these terms).
 * HgH, the other article edited recently, is another difficult one. There is a lot of information added over the course of months, still the references are the same (see here where Plasmic Physics is adding a whole section .. without any references).  (following not really due to Plasmic Physics:) One of the three is a Chem. Rev. article by Simon Aldridge, which mentions mercury hydride only minimally.  Overall, I found it difficult to attribute the statement to those articles (I think that the attribution to the review is plainly wrong).  (now back to Plasmic Physics:) Most of the new information is completely unreferenced, and in the latest edit he changes the 'also written' way to a form which I did not see in the supplied references (he has been edit warring about it in the past, found a compromise which now was removed so it is finally gone).  Looking from the reader side, I find it completely wrong.
 * Agree that acidity should be covered first, but reactivity of the carbonyl is also a central concept (see, e.g., the development of carboxylate reactivity at this esteemed site: . Absolutely concur that an outcome of this (and every) Wikipedia discussion should be to dissuade individuals who add material without citations, and to sanction them if they repeatedly do so, per WP policies on verifiability. This all the more since most chemistry contributors are not graduate trained or professional chemists. Le Prof  Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
 * Now that writing in a way that is harmful to the reader is recurring. As is the writing of systematic names, systematically writing of formulas, alternative names, etc.  As is the lack of references.  And the (slow) rewrite of articles to cover a completely different subject is another theme of recurrence (here mentioned in cyclopentadienyl, in a way it is also in mercury(I) hydride, though that was not too established and maybe plainly incorrect in the beginning) and even worse than harmful.  I regard the bold rewrite of cyclopentadienyl to be close to destruction of the article, extremely harmful to the reader and to Wikipedia, and if Plasmic Physics does not understand that, I think that a long ban from all chemistry related subjects, broadly construed, is in place.  --Dirk Beetstra T  C 04:10, 6 May 2014 (UTC)
 * I do not know the history of this matter, nor have I time to enter into it. I would say that the issues being raised are very important; though the editor appears well meaning. Perhaps he will respond to a final warning to (i) make no substantial edits without clear evidence that reflect the preponderance of professional chemistry opinion as evidenced in the best texts and secondary references, and (ii) that, given his apparent history with this community, he place a note in the talk page discussing significant proposed edits prior to editing (a rarity here, but something I routinely practice). If he does not respond to such, then perhaps, if indeed there is a long disruptive history, he will have to experience a block to understand that consensus is required (and that his antennae for sensing whether his edits will achieve consensus post hoc are seriously mistuned).  Le Prof  Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
 * Plasmic Physics undid my revert of the change in Acetic acid (diff), changing the sentence "The OH group is the main site of reaction, as illustrated by the conversion of acetic acid to acetyl chloride." to "The CO group is the main site of reaction, as illustrated by the conversion of acetic acid to acetyl chloride". His argument: "Incorrect, OH is predominantly involved in acid dissociation."  We are not talking about acid dissociation, the only conversion that is illustrated by the change of -COOH to -COCl is the .. change in the OH group into a Cl group.  I hence stand with my suggestion of a long term restriction from Chemistry articles, broadly construed.  --Dirk Beetstra T  C 11:10, 6 May 2014 (UTC)
 * Disagree. The formation of acid chlorides is perhaps best described as going through a pericyclic transition state, and this reactivity clearly involves the carbonyl as well as the acidic proton (see, a site run in conjunction with the fine Clayden text); the same is true of the PCl5 mechanism. Note, formation of acid halides, anhydrides (e.g., with P2O5 or modern methods), etc. are generally done under anhydrous and apolar solvent conditions, suppressing formal deprotonation/oxyanion formation as a prior discrete step to further reactivity—no? Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)


 * I support banning Plasmic Physics from editing chemistry. I just dont see any upside to his participation. If he is banned from chem and moves to another project, god help that project! --Smokefoot (talk) 12:36, 6 May 2014 (UTC)
 * This is a rush to judgment and I do not agree. Blocks and bans are serious steps. Annoyance is simply not enough. Edit conflicts can (and judging by the following discussion) post hoc will in this case actually serve to improve content. Silencing a dissenting voice in the case of the issues appearing here may make things more peaceful, but they will not automatically provide the highest quality content.  And that is the aim, no?  Bottom line, this community has not shown me either that it is rightly adjudicating the science, or that it has exhausted other less extreme actions aimed at shaping editor behaviour.  Le Prof   Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)


 * Just to comment on the specific edit to Acetic acid that is being discussed Plasmic Physics is right that in the conversion of acetic acid to thionyl chloride is a substitution of an OH with a chloride with the carbonyl as the reacting centre. I can try and source a reasonable off wiki source but for now I'd cite [] see the Carboxylic acids section which shows the mechanism - I'd actually suggest that this conversion from acid to acid chloride is less than ideal as it isn't a good example: it is less straightforwards than an a basic esterification. And relating to the point Dirk Beetstra is making; carboxylic acids tend to undergo acid-base reactions over substitution reactions unless you start to look at more complicated mechanisms/reagents. So I guess I'm saying both points are correct and it is probably that the content in this section needs re-working to make it clearer (rather than this small edit about where is reacting.) --The chemistds (talk) 12:53, 6 May 2014 (UTC)
 * Astute comments, see above for linked site in support of this User's claim. Le Prof  Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)


 * A few observations: (1) Plasmic has produced a lot of disruption over time, but he's not always wrong; (2) On cyclopentadienyl, he is correct that the name is not correct for the isolated anion but rather for the radical or the anion when it is a ligand. I would suggest a making cyclopentadienyl a dab page linking to an anion page (under cyclopentadienide which is already a redirect, adding redirects from cyclopentadienyl ion and cyclopentadienyl anion and borrowing from the current page as Beetstra prefers it), a complex page (which already exists) and a page at cyclopentadienyl radical using material from the Plasmic version.  The substituted cyclopentadienyl radicals are well known as reactive intermediates in this area of chemistry; (3) on acetic acid, it is bad practice to refer to a carboxylate functional group as a carbonyl and a hydroxyl, it strikes me as similar to arguing about whether walking is centred on the ball or the heel of the foot.  EdChem (talk) 13:25, 6 May 2014 (UTC)
 * Astute comments, though the -yl form is acceptable if followed by anion, and indicative of the radical if not. Otherwise, kudos, well spoken.  Le Prof  Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
 * Comment: Yes, cyclopentadienyl is the name for an (esoteric) radical. But look at what Plasmic did to it recently  Edits made by Plasmic often have some element of fact to them, the issue is with persistent abuse of WP:UNDUE and persistent (and I really mean persistent) problems with imposing weird nomenclature.  His work often relies on narrowly selected literature to support his flawed grasp of chemistry. --Smokefoot (talk) 13:39, 6 May 2014 (UTC)
 * Esoteric, no. I am neither a radical chemist, nor an OM chemist, but an OChem/medichemist and educator, and say, strongly, both definitions belong in an encyclopedia. That, at this moment of history, in the literatures that this group are most fluent, the anion is most prevalent, does not speak to fundamental importance of the anion, nor does it support exclusion of the important observation that the -yl radical can be formed from the parent hydrocarbon. Indeed, in the history of physical organic chemistry, both are equally and seminally important (insofar as understanding organic structure and bonding, molecular orbital theory in OChem, delocalization and aromaticity, etc. are concerned). One man's esoteric may well be a fundamental concept on which much deep understanding is based.  Le Prof  Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
 * I agree that PP has caused lots of problems, and in saying he is correct I was thinking more of a post he made at Dirk's talk page than his changes to the article. Certainly his nomenclature work is irritating (at best) and his grasp of chemistry is highly variable.  I thought the last time he started taking large actions that a topic ban would be appropriate, and I am not opposed to it, but I maintain that he has a point here and put forward an option that would both direct readers correctly and be chemically acute.  I also just changed where the thallium cyclopentadienide article was linking Cp to cyclopentadiene and my suggestion would provide better targets.  EdChem (talk) 13:51, 6 May 2014 (UTC)
 * Again, if the standard is that there is to be no substantial editing by PP or the rest of us, without addition of relevant, quality 2o or 3o citations, then the nomenclature editing problem goes away. There is absolutely no excuse in this decade of this millennium for nomenclature issues to be contentious; every such entry can and should be supported by (i) an IUPAC citation (online, for heaven's sake), and then a second practical reference. e.g., to a high quality teaching text like Clayden, or to an industrial chem guide, as is relevant. (The latter, because IUPAC tries to shape what practicing OChemists do in their "name-calling", but they are not always successful. That the IUPAC called the recent newsworthy carbinol "(4-Methylcyclohexyl)methanol" is only (just) as important as the fact that the news media and industrial enterprises still know it as "4-Methylcyclohexanemethanol" or "MCHM"—which Wikipedia has, thankfully, gotten correct.)  Le Prof  Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)

My next 2p. If people in newspapers, on internet, wherever encounter the term 'cyclopentadienyl' it is always consistently with respect to the Cp-complexes of metals. That is what we are writing Wikipedia for, those readers, not for the chemist. Even if that cyclopentadienyl does not follow the systematic IUPAC naming, it is what we chemists say, it is what chemicals companies call compounds with it, and it is what newspapers would say when referring to cyclopentadienyl-containing compounds. If that reader types into Google 'what is a cyclopentadienyl', they expect Wikipedia to come up with that term for this anion. Not for the free radical, not for the functional group (as in an organic compound). I therefore think that Cyclopentadienyl should be about the anion, and there could be dab-links at the top, pointing to the cyclopentadienyl-radical (the free compound) or the cyclopentadienyl-functional group in organic chemistry (if that has enough body to have an article). It may not be chemically/IUPAC 100% correct, but I firmly believe that that is what the reader expects to find when they look for cyclopentadienyl after they encounter the term somewhere (making it a disambig will only confuse them). (by the way, I think that Thallium cyclopentadienide is a bad example, it redirects to Cyclopentadienylthallium, with the commonly used, though likely in conflict with the systematic IUPAC rules, cyclopentadienyl). And you see, we are back at the point of nomenclature.
 * ''I am sorry, no, Ed, here we disagree. We are writing to shape broad understanding of a field, and to correct as well as to inform as we go. Change the article title to "Cp anion", or make room for both concepts (anion and radical). See my earlier comments about the importance of organic radicals to theory, history, and mechanism in OChem. That google searches pull up the one now is a matter of public popularity only, and not a guidance for science writing! Moreover, Google is a purely commercial enterprise, only the poorest of academic search tools, certainly vis-a-vis chemistry searching; its prioritization of reported hits is not under user control. (Santorum neologism. Need I say more?)
 * If one wants the real lay of the land, one always uses two separate search tools, and then holds the perceptions generated with an open hand (mind). Search the Cp term in its written out form at the ACS portal, and then in the Beilstein. Yes, you will see the anion, but the radical is also there—and all the more if you constrain searches to particular periods. The overwhelming ubiquity as much speaks to the timing of the emergence of the Cp anion in chemistry relative to emergence of the internet, as it does to anything fundamental to chemistry. As well, the best OM chemists (e.g., Bosnich trainees from Chicago) would always speak of the "Cp anion" in formal settings (seminars, papers, etc.), though in lab perhaps truncate the expression. The encyclopedia is such a formal context.  Bottom line, the word refers to both organic structures. Either disambiguate "cyclopentadienyl anion" and "cyclopentadienyl (radical)" as IUPAC and all teaching chemists do in formal writing, or make room for both in the one article.  Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)

Regarding acetic acid, the example given is confusing, and the mechanism of it is canonical, simplified. Basing on that mechanism the conclusion that the CO is more reactive than the OH is IMHO wrong .. but the core of the problem is not that, I wonder in how far we can correctly say that a -COOH group has a C=O and a C-O-H anyway. And in a way, this is close to the same problem as the nomenclature - this sentence shows thinking of a COOH group as a keto-function and alcohol function. The problem lies deeper. --Dirk Beetstra T C 14:18, 6 May 2014 (UTC)
 * See my comments above about the cyclic transition state. Agreed, the matter arises because of oversimplification of the reaction mechanism, both at the article and in this discussion. Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
 * What I don't understand about your position is that if readers would be seeking "cyclopentadienyl-containing compounds", why not focus on cyclopentadienyl complexes rather than the anion? Maybe we need an article on the complexes with sections on synthesis to discuss the anion and radical?  EdChem (talk) 14:34, 6 May 2014 (UTC)
 * Ed my respect for you grows and grows. Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
 * I think that the incoming search term from a non-chemist would be 'cyclopentadienyl', not 'cyclopentadienyl complex'. We do not strictly adhere to the IUPAC naming, but to what is commonly used.  Cyclopentadienyl is commonly used for the cyclopentadienide anion - practically all our complexes with a cyclopentadienide anion have the term cyclopentadienyl in their (current Wikipedia page-)name.  --Dirk Beetstra T  C 14:39, 6 May 2014 (UTC)
 * No further comment on this. Professional opinion clearly stated. Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
 * In a way, this is what I mean, it is a persistence of Plasmic Physics to align Wikipedia completely with the systematic IUPAC nomenclature and other IUPAC rules. That sometimes conflicts with what is the common use, which is the consensus that we have that we will use ("Generally, article naming should give priority to what the majority of English speakers would most easily recognize, with a reasonable minimum of ambiguity, while at the same time making linking to those articles easy and second nature.", from WP:MOSCHEM/NAME).  We don't call the article (6R-trans)-6-(1,3-benzodioxol-5-yl)- 2,3,6,7,12,12a-hexahydro-2-methyl-pyrazino[1',2':1,6] pyrido[3,4-b]indole-1,4-dione (we don't even have the redirect) - we don't follow the systematic way of IUPAC there, we use the name that the is commonly used, and even the name that is used by most of not all chemists, even if that is in conflict with IUPACs systematic rules.  Cyclopentadienyl is the name that mostly denotes the cyclopentadienide anion, unfortunately in conflict with the systematic IUPAC rules.  --Dirk Beetstra T  C 14:45, 6 May 2014 (UTC)
 * Apples and oranges, mate, and a straw man argument to boot. To ask disambiguation of anion and radical is not the same as the game-playing you are doing with the IUPAC name for tadalafil. In the one case, the two refer to two different chemical entities, with differing reasons for importance. In the latter, it is a to-may-toes / to-mah-toes issue (or better, a tomatoes / viiniköynnöksen kypsyneitä tomaatteja issue, if you speak FInnish). Let's call the whole thing off, indeed . Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)

I have been following this discussion with some interest. First, I am not happy about how this is being handled. Nobody has seen fit to talk to PP directly on his talk page, even to point him here. Second, I tend to agree with EdChem here, but there could be a variety of solutions. The article could discuss both the anion and the radical, although the discussion of the anion should be first. You should be looking for compromise and ways of educating PP, not just reverting him. -- Bduke   (Discussion)  22:54, 6 May 2014 (UTC)
 * I am late in coming to the discussion; if this observation is indeed correct, shame on us. Le Prof  Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
 * I am sympathetic with the spirit and the letter of your advice. We are here to help not only the readership but each other.  But when is enough enough? Review the agonizing process by which User:Axiosaurus and others coaxed borane and related articles from his grip.  One needs a tag team to cope with his writing, and he can be a prolific editor.  So in terms of your advice of "educating PP", that experiment seems to have been tried, repeatedly.  He has been reprimanded for editing chemboxes, nomenclature, categories.  Now look at PP's very recent edits of cyclopentadienyl:
 * "The 2λ3-propane-1,2,3-triyl-1,3-diylidene group (⩾CC(R)C⪕) in 1λ3-cycloalk-2-(di)enes such as cyclopentadienyl can accept or donate a single electron by association:
 * + R →
 * Because of this acceptance or donation of the electron, cyclopentadienyl has radical character. It is a highly reactive monoradical. Its functional group is cyclopenta-2,4-dien-1-yl ."
 * He's been an editor for how many years? The lack of PP's progress and the requirement for chaparoning his work are semi-exasperating.  Not a crisis, but exasperating.--Smokefoot (talk) 02:05, 7 May 2014 (UTC)
 * Propose firm boundaries, here: short of a ban or block, what specific constraints would you like, please? Though the edits might be misguided, the chemistry issues are not as simple as were initially represented. What specifically would you like PP not to do?  I have suggested some elements of a proposal, that can be cut-paste-edited into your bullied proposal.  At this stage, I will fight a block or ban.  Le Prof  Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)


 * User:Bduke - Plasmic Physics is not a new editor here. He should know process.  Though I agree that he should have been informed about this discussion here (I did mention it to him on my talkpage when he came to discuss .. well rather complain about .. the reverts; did he not get informed?  User:Beetstra WP:WIKITROUTs User:Smokefoot (knowing full well that Smokefoot linked Plasmic Physics' username, so he got pinged).  It does however not invalidate the discussion, nor make the problem disappear).
 * Still, shame on us. Was the conscious point of excluding him in notification, to have a private discussion first, to build an inevitable momentum?  If so, all the more…  Le Prof  Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
 * Regarding the reverts, I have been reverting with an edit summary. At that point the discussion could commence.  When that does not happen but he simply re-reverts then that does not help.  And especially with cyclopentadienyl, I again stress, it is the problem that is appears that Plasmic Physics enforces all articles to follow the IUPAC recommendations for systematic naming.  That is not how Wikipedia operates, neither is it normal operation that if someone reverts your bold changeover back to the long-standing version that you then engage in reverting.  Similar is the changeover to Acetic acid, where his changeover is canonically correct, though chemically senseless (the observer will say 'I thought that acetic acid was an acid, which means in my high-school chemistry that there is a proton (H+) involved .. and now you tell me that the main reactivity is because of the C=O?).  And that is actually because there is a deeper problem with that sentence, which does not get recognised.
 * The "enforces all the articles to follow the IUPAC" matter can easily be addressed in a disciplinary proposal short of a block or ban. And what you are terming senseless is clearly something that I believe, as a career research chemist and educator, involves nuance that you are failing to acknowledge. Le Prof  Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
 * The common denominator between the cyclopentadienyl and acetic acid situation is that both are 'problems' (they are both in the grey area between two 'correct' situations). Plasmic Physics boldly changed them over from one correct situation to another correct situation, and I recall similar cases from the past (this is not the first time that his prolific work to an article got reverted).  The recurring (and exasperating) problem is that Plasmic Physics does not always seem to know the line between 'should I discuss this', 'should I boldly change this', or 'should I leave this as is'.  He does great work (albeit a bit too technical, and having some issues from the reader/accessibility side, methylidene is a good piece of information, that is something we can build on), but he should understand that sometimes it is better, especially if it involves long-standing articles on terms which are very common like cyclopentadienyl, to bring his discussions first to a wider audience and wait (and understand that if such a discussion does not come to a close, that that does not automatically needs to mean that there is consensus to change), and if there are changes that are without consensus that get reverted, that then the same discussion-wait-for-consensus-situation should take place.  --Dirk Beetstra T  C 04:02, 7 May 2014 (UTC)
 * In re: an emerging proposal, see above for the second of two points, that significant editing be preceded by Talk. Generate a firm, fair disciplinary proposal, based on what you have heard from me, and others that do not completely agree with you. Post that new proposal below. Remember, what is good for the goose, is good for the gander. Le Prof  Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)

The following was posted on my talk page,

There is a long discussion about your edits to chemistry articles at Wikipedia talk:WikiProject Chemistry#Here we go again with Plasmic Physics. I am disappointed to see that you have not engaged there and responded to the criticisms. Please do so, and we might then come to some kind of resolution. Ignoring criticism never helps. -- Bduke (Discussion) 06:11, 7 May 2014 (UTC)

To Bduke: I have not engaged, because my input is never regarded. In every case, the outcome have always resulted, irrelevant of it. It usually results in either a stalemate, or a symptomatic involuntary cat-and-mouse resolution, which is evidently non-effective. I say involuntary, because it tends to arise unintended and spontaneously. That said, I do agree for the most part, with Beetstra's interpretation at 04:02, 7 May 2014 (UTC). However, identifying the problem is only one side of the coin. Unless a resolution is devised and implemented, any interpretation is useless. If any one does indeed require my input, then I would appreciate direct questions. Plasmic Physics (talk) 07:29, 7 May 2014 (UTC)
 * This is not helpful. No wonder, editors here are frustrated. You address none of the issues raised above. Why do you think the quoted paragraph about the radical is appropriate? Why did you change the article from being about the anion to being about the less important radical? Why do you persist in using IUPAC nomenclature strictly when there is a clear consensus in this project to be more flexible to make things more understandable to our readers? I could go on. -- Bduke   (Discussion)  21:04, 7 May 2014 (UTC)
 * Stop with the "less important", please. Le Prof  Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)


 * In reply to the first and second questions: I think that the quoted paragraph is appropriate, because of four points:
 * Occam's razor indicates that if "cyclopentadienyl" is even partially systematically named, then it must be a radical.
 * References to unqualified "cyclopentadienyl" supports this interpretation.
 * Misinformation should be extinguished in Wikipedia.
 * The content of the initial version would not be lost, as it was a subset of another page: Cyclopentadienyl complex.
 * How do you suppose I am using "IUPAC nomenclature strictly" rather than being flexible? Please do go on. Plasmic Physics (talk) 02:21, 8 May 2014 (UTC)
 * Well, at least you are addressing the points made above. Your first two points however reinforces for me the point made above that you do not really understand chemistry. For any chemist, if the term "cyclopentadienyl" is used, he/she thinks of the anion. I do not understand your forth point. As far as the last point is concerned, I was just referring to the points made above. -- Bduke   (Discussion)  02:41, 8 May 2014 (UTC)
 * Please, all, stop with the "For any chemist" generalizations. Words have meaning in context. In an OM context, yes. In other contexts, not necessarily. In a formal setting such as an encyclopedia, not necessarily at all. Le Prof   Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)


 * I did say unqualified Cp. My fourth point refers to how a similar version of the same content is present in the referred article. Seeing as how neither of us then recognizes the substance of the above accusations, perhaps then someone else can divulge. Plasmic Physics (talk) 03:08, 8 May 2014 (UTC)


 * Occam's razor .. in other words, you are arguing that the naming of pages on Wikipedia should follow IUPAC systematic nomenclature to the letter because everything else needs the assumption that there is an unreliable factor out there: what does the reader want? I'd like you to quote which part of the naming rules in any part of the MOS, or in any of our policies we use that as the argument for naming.
 * Practically all cases where Wikipedia is using 'cyclopentadienyl', it is about the anion (Cyclpentadienylthallium, etc.). Now you could argue that those are all to the qualified cyclopentadienyl, it is what Wikipedia by far talks the most about.  If we have 50 articles with the word 'cyclopentadienyl' in the title, all talking about the anion, and then the editor who wants to know more about that is led to an article about the radical .. having to figure out through the dab that they has to be somewhere else, at cyclopentadienide, is, to say the least, confusing.
 * NO. The naming MOS made the specific choice that sometimes we do not follow the correct term, and if that is properly explained, that is not misinformation.
 * That last point has some truth to it .. although 'cyclopentadienyl' is not necessarily always talking about the complex, if you would have said 'cyclopentadienide or cyclopentadienide anion' that may have been an idea. But say that we have consensus to go to the systematic nomenclature, and we put 'cyclopentadienyl' at 'cyclopentadienide anion', and we make 'cyclopentadienyl' about the radical / functional group (difficult choice between the two, and they are really very closely related).  In that case, we do not (gradually) change over the articles from one to another (confusing the edit history).  What we do is we swap the titles through a move.
 * To me, one of the problems, Plasmic Phycics, is your interpretation and (way of) following of IUPAC systematic nomenclature. Moreover, your reasoning not to discuss is that it does not get to a consensus and hence that there is no need to discuss.  And it is not the first time that you have been pointed to how you handle these situations, and that many editors on the chemistry wikiproject think, and seen you current restriction also some editors outside of that, that that behaviour has to change.  Do you understand that it is, in the end, the same editing behaviour over and over that is resulting in editors having concerns over your edits?  What would you suggest to do so that those concerns will not arise again?  --Dirk Beetstra T  C 04:14, 8 May 2014 (UTC)
 * That Wikipedia does anything consistently is the poorest of arguments for validity. Much content here is unsourced, and student-generated. Make claims based on verifiable sources, even here. While poorly fought, the anion v radical issue is a potentially valuable, content-clarifying matter. Resolve the core issue.  Stop arguing about (i) the semantics, and (ii) the argument itself.  PP, you as well.  Bring it home.  Le Prof  Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)


 * Regarding your first point: no, I'm not arguing that at all, I'm explaining on why my interpretation is logical.
 * ...Second point: by "unqualified cyclopentadienyl", I am referring to occurrences of the word cyclopentadienyl in isolation - not a segment of another systematic name, or an adjective.
 * ...Third point: that is only true if you can justify with references that it is acceptable to figuratively call an apple an orange.
 * Often my reason for not discussing is the invocation of a discussion it is used to legitimize ignoring my query, and so prevent me from making any changes whatsoever. Another reason for not discussing, is because I do not think it necessary. Plasmic Physics (talk) 05:49, 8 May 2014 (UTC)
 *  Whatever reason you might have for not discussing a substantial edit a priori, PP, it does not excuse you from the WP policies concerning consensus. Do you believe if you make a series of edits below radar (unseen for a time), such that reverting them is more difficult, that it will provide an alternative course to the WP required consensus? Clearly, this wall of discussion must persuade you that that strategy is a failed approach. No, there is no excuse for repeatedly trying to pull an "end around" the community, getting in edits that you believe, if discussed, would not result in consensus. Do the hard work of wikipedia; call on other chemistry editors such as me, and attend to the core chemistry issues. If this had been done, you would have been set back on your heels at times about use of IUPAC names, per se, but we likely would have (i) the anion and radical both appearing and differentiated (in same or different articles), and would have had (ii) a better, more accurate mechanism for carboxyl reactivity (cyclic TS, instead of errant UG ideas). Bottom line, you better start to see that your approach is neither proper nor productive, or the community will have its way.  Le Prof  Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)


 * 1) I was not arguing that the interpretation was illogical.
 * 2) Yes, I understand. And how much of the unqualified use of the term cyclopentadienyl do you see over the qualified (as anion) use of the term.  Because MOS suggests to use the common use of the term.
 * 3) Per 2, by far most of the information out there is using the term talking about the anion.
 * I know why you don't discuss, and that is another part of the problem. Your last sentence is even more concerning.  --Dirk Beetstra T  C 06:00, 8 May 2014 (UTC)


 * 2) It is actually relatively rare to find a mention of unqualified "cyclopentadienyl". There are plenty of "Cp ligand", "Cp anion", "Cp cation", "Cp complex", and systematic names containing Cp, but rare ever just "cyclopentadienyl".
 * By my last sentence, I'm not saying that I never discuss, because of that reason; I'm saying that I occasionally don't discuss for that reason. Plasmic Physics (talk) 12:10, 9 May 2014 (UTC)


 * "It is actually relatively rare to find a mention of unqualified "cyclopentadienyl". So then we need to go by the qualified use, which is in most cases the anion or ligand .. and that is what the article was at.
 * And it is that not discussing when it is necessary what brings you here all the time. --Dirk Beetstra T  C 04:15, 11 May 2014 (UTC)


 * Then the article should be renamed to a correct title. Me not discussing when it is necessary has been established in previous discussions, as has that "necessity" is a matter of perspective. Plasmic Physics (talk) 12:06, 11 May 2014 (UTC)
 * Perhaps now, finally, we are getting somewhere. Le Prof  Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)


 * No, it should be at what is the most common use, not at what is correct according to the IUPAC nomenclature. --Dirk Beetstra T  C 12:16, 11 May 2014 (UTC)
 * Alas back to square one. Dirk, no, a thousand times no. The term polyphenol—for non-polymeric substances, that, as oligomers of phenols of particular structures, give teas and berry jams their darker colour tones—has been highjacked, both in the web, and in poorer academic venues, in pursuit of the fact that true polyphenols have clear potential medical benefits. Does the Wikipedia article therefore simply take on the web-based mistaken attributions of commercial nutriceutcal suppliers or H-index pursuing scientists?  No, this is fundamental mistake: failing to differentiate between lexicography (the tracking of the evolution of word meanings in common use) and scientific nomenclature (the establishment of technical meaning so that use of specific terms with such meanings remain defined and fixed over large tracks of time, so as to add convenience and precision to scientific discourse). If we mean Cp anion, say Cp anion. The hallway talk outside an OM lab is not formal chemical communication.  For the last time, please: encyclopedic articles are formal venues of communication, and the two meanings of the term need to be disambiguated. There is fundamental validity to PP's point.  Le Prof    Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)


 * I've already showed how it is one of the least common uses. Plasmic Physics (talk) 12:19, 11 May 2014 (UTC)
 * Almost all, if not all, of the mentions of cyclopentadienyl on Wikipedia are to the qualified anion/ligand .. and that is where the public would encounter the word. The public does not know what that cyclopentadienyl stands for, and they should be directed to the correct article if they search in Google for cyclopentadienyl.  Not to the radical, which is utterly confusing for the casual reader (even with a dab pointing to the anionic/ligand use of the term).
 * In any case, this changeover is contentious, obviously, and should have gone through discussion first, and, if consensus would be that way, not through a changeover but through a move of the articles. --Dirk Beetstra T  C 12:25, 11 May 2014 (UTC)


 * Exactly, rarely if ever does Cyclopentadienyl implicitly refer to the anion, both on Wikipedia and on Google. If you are so adamant, find me three counter examples. Well, now I know that it is contentious. Plasmic Physics (talk) 12:36, 11 May 2014 (UTC)
 * Oh for goodness sake: rarely if ever are people talking about the radical or the cationic form of cyclopentadienyl. They are rare.  The only way you see the term is in the qualified form (but the non-chemist does not understand that, for them cyclopentadienyl is just a term, they do not know if it is the functional group there, the anion, the radical or the cation, they likely don't even know what it is; for a chemist, 'cyclopentadienyl sodium' is qualified as the anion, but the man in the street does not know that), and when they find that on Wikipedia, they should be on the page which explains them the term that is by far, far the most mentioned form: the anion.  The article should then clearly state the things there (there are 'three other forms', some or all have their own article, etc. etc.).
 * In any case, rewriting such articles, especially when they are long-standing is not the way forward. That messes up the history of an article, or even of a set of articles.  --Dirk Beetstra T  C 03:40, 12 May 2014 (UTC)


 * That is why I agree with the prior suggestion of creating a disambiguation page. Plasmic Physics (talk) 04:27, 12 May 2014 (UTC)
 * No, you first changed the article over, then you agree with the creation of a disambiguation page. But do note that I still think that by far most of the times that the word 'cyclopentadienyl' is used somewhere, it is for the anion, and that hence cyclopentadienyl should be discussing the anion (or be a redirect to the more correct cyclopentadienide), and the article should be pointing to either the 3 other, way, way less common, possibilities of what the term may mean, or to cyclopentadienyl (disambiguation) .. but a discussion will either lead to that consensus, or we stay with the status quo that we have.  --Dirk Beetstra T  C 05:15, 12 May 2014 (UTC)


 * I was not stating happened, but what I prefer to occur. And I still think a thoroughly thunk through thought, which is that Cyclopentadienyl should be a redirect to Cyclopentadienyl (disambiguation), with three listed pages: Cyclopentadienyl complex, Cyclopentadienyl cation, Cyclopentadienyl anion, and Cyclopentadienyl radical. Since we're reaching a stale mate, at least a third vote is required. Plasmic Physics (talk) 07:49, 12 May 2014 (UTC)


 * On the acetic acid article, the edited statement needs a reference either way. The references on the paragraph do not actually talk about which part is more reactive. This is a featured article, so any statements need a reference.  And in reality doesn't the hydrogen move between oxygen atoms anyway? Graeme Bartlett (talk) 22:16, 8 May 2014 (UTC)
 * Concur with referencing. The "which part is more reactive" prose is indicative of either fast composing (I'm guessing) or loose thinking. With ambient nucleophiles, bifunctional compounds (and which important substance we study is not that, or much more), etc., such words become near to meaningless. Yes, in Chem 1, we can say of an alkanal, that the aldehydic carbonyl is more reactive (than the remaining hydrocarbon chain). But, first, this is an encyclopedia (meaning we do not generalize to the point of losing accuracy of statement, rather we elaborate and qualify to remain accurate), and second, such simplifications are simply irrelevant to matters such as acid chloride formation, where both the carbonyl and acidic hydroxyl participate in perceived mechanisms of the reaction (again, see !). Look at the modern protecting group-free chemistry work, for goodness sake; what is reactive depends entirely on the conditions into which the molecule is placed. I am guessing any of us can now find literature on a bifunctional organic that, under the correct conditions self-protects/masks, allowing chemistry to proceed on the least reactive functional group. Never lose sight of the reality, in simplifying explanations. Le PRof    Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)


 * The alteration indented to indicate which part is attacked first. Yes, acetic acid does protomerically tautomerise, but both tautomers are degenerate, and in either case, the terminal oxygen is still the part which is attacked first, like a molecular game of keep-away. Plasmic Physics (talk) 12:10, 9 May 2014 (UTC)
 * I doubt that in free acetic acid you can even pinpoint in the initial state where the hydrogen is, and likely hydrogens are bound to both oxygens, and which of the two oxygens is doubly bonded is not extinguishable. --Dirk Beetstra T  C 04:15, 11 May 2014 (UTC)
 * Once again, I point you to the Liverpool site, which is associate with the fine Clayden text. This discussion regarding "which part is attacked first" is utterly naive. As if the arrowed mechanisms drawn in first semester OChem reflect some hard, incontrovertible physical reality. Moreover, more generally the foregoing and following discussion is generally meaningless, generally nonsensical unless a specific context is stated clearly. Via many experimental methods, and at many experimental time scales, one "sees" no hydrogens at all—they are either moving too fast, or invisible to the technique. Stop arguing this, both sides. Outside of a specific block of article text, it is a waste of time. What is the point: What do both sides here want, and how can we achieve it?  Le Prof  Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
 * That is not what spectroscopic studies reveal - the oxygen atoms are non-degenerate for carboxylic acids, which would be the case if the hydrogen atom was bridged between them. Plasmic Physics (talk) 12:06, 11 May 2014 (UTC)


 * . --Dirk Beetstra T  C 12:16, 11 May 2014 (UTC)


 * It is a basic fact learnt in the first years of university. I'm sure if I tried I could find a reputable source, but for a lack of trying, our page on Carboxylic acids states it clearly. Plasmic Physics (talk) 12:26, 11 May 2014 (UTC)
 * Out of your league here PP. That a spectroscopic Pchem study can be found showing localization of a proton in a carboxylate system (what, at ultralow temperature? in crystal? in a 1,3-dione system?) is irrelevant to what is seen and studied in solutio, by practicing organic chemists, and these make up a significant portion of the audience you are writing for, and the fellow editors whose consensus you must reach . Here I am solidly on the side of the other voices. You simply are extrapolating from the wrong type of data to a generalization that is not valid. For goodness sake, hydrogen atoms tunnel; no scientist worth his salt stakes career on where a proton comes from in a mechanism, and few are doing the very careful mechanistic work to even to begin to approach such questions. Generally, mechanisms are a combination of inferences of reaction outcomes over a variety of systems, to which is applied "chemische Gefühl" (chemical intuition, the traditional approach), and now, selection among the inferred options based on solid computations (modern addition).  Bottom line, arguing localization in simple, unconstrained organic structures, in solution at ambient temperatures and above (i.e., under conditions relevant to the chemistry of life, to pharmaceutical and other synthetic chemistry efforts, etc., etc.)—or arguing what part of a carboxylate is first to react—this is naivety beyond comprehension.  Both sides, please, consider it a lost battle; this is so much embarassing balderdash. Sorry.  Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)


 * Please find a specific reliable reference Plasmic. If it is as you say then textbooks should say it.  Wikipedia itself is not a reliable source for Wikipedia. Graeme Bartlett (talk) 21:34, 11 May 2014 (UTC)


 * . Plasmic Physics (talk) 23:38, 11 May 2014 (UTC)


 * It’s a long time since I was in chemistry—and I never got past “the first years”—but that agrees with my recollection. I can’t find an explicit statement to that effect in my old textbooks, but the following exercise question & answer would seem to support it: “[Q:] Why is resonance more important in the carboxylate ion than in the carboxyl group itself? [A:] Two equivalent resonance forms exist for the carboxylate ion.” ISTM that if the -COOH hydrogen were equally associated with both oxygens, the acid’s resonance structures, as well as the ion’s, would be equivalent.—Odysseus 1 4 7  9  00:07, 12 May 2014 (UTC)


 * And just think of the ring strain that a double association would impart. Plasmic Physics (talk) 00:51, 12 May 2014 (UTC)
 * Well, if the H were conceived as having half a bond with each O, one might expect such bonds to be extra-long (albeit not as long as an intermolecular H-bond), making for a less-strained configuration than that of e.g. cyclobutene.—Odysseus 1 4 7  9  02:22, 12 May 2014 (UTC)
 * On the other hand, I suppose a doubly associated form should exist as a transition state between tautomers. Plasmic Physics (talk) 04:43, 12 May 2014 (UTC)
 * Almost there, Plasmic Physics, I see you took the hint that I gave below. --Dirk Beetstra T  C 05:15, 12 May 2014 (UTC)


 * Not so, by definition a transition state represents a non-existent configuration for a molecule that serves purely as a heuristic model of a reaction mechanism. Plasmic Physics (talk) 06:57, 12 May 2014 (UTC)
 * That is why I said you were almost there - it is not a transition state, and a transition state is a existent configuration (it has fleeting existence), though likely with a extremely short lifetime. --Dirk Beetstra T  C 07:43, 13 May 2014 (UTC)


 * You confuse, the transition state for reactive intermediate. There was a reason that I Wiki-linked it. Plasmic Physics (talk) 11:49, 13 May 2014 (UTC)


 * You all are confusing, all talking past one another, and all tremendously off point. The question at hand, is whether PP is editing in such a manner as to require a block or ban. I have arrived at a qualified conclusion. The rest of this, apart from a specific context—carboxylic acid esterification under Fischer–Speier conditions, vibrational cryospectroscopy of formic acid, depsipeptide hydrolysis catalyzed by chymotrypsin—has little chance of being resolved here. Can we agree to leave this until we have an actual text that we are editing, and then, someone propose a sentence, in talk, in that particular context, so this discussion can conclude ?  Otherwise, you are also confusing time with a commodity that is in endless supply.  Le Prof Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)


 * See where I take the term 'fleeting existence'. And that something can not be seen does not mean that it is a non-existent configuration.  --Dirk Beetstra T  C 05:28, 14 May 2014 (UTC)


 * By the definition of a transition state, it does mean exactly that. Plasmic Physics (talk) 08:03, 14 May 2014 (UTC)


 * When I look for that, the Google ebook only has under 400 pages, so cannot be verified. So can you quote a few words about that that says in your reference? Graeme Bartlett (talk) 08:54, 13 May 2014 (UTC)


 * "The carboxyl group of a carboxylic acid gives rise to two characteristic absorptions in the infrared spectrum. One of these occurs in the region from 1700 to 1725 cm-1 and is associated with the stretching vibration of the carbonyl group. This region is essentially the same as that for the absorption of the carbonyl groups of aldehydes and ketones. The other infrared absorption characteristic of a carboxyl group is a peak between 2400 and 3400 cm-1 due to the stretching vibration of the O-H group."
 * It goes on to say that the difference in the spectrum between a single molecule and a dimer, is that the O-H peak is broadened for the dimer. Plasmic Physics (talk) 11:49, 13 May 2014 (UTC)
 * Thanks Plasmic. So it confirms what you said here, but not what the change or pre-change of the acetic acid article said about a group being more reactive, but instead that the groups are distinct. Graeme Bartlett (talk) 13:29, 13 May 2014 (UTC)
 * As I said, this is getting there. What is acetic acid (or any carboxylic acid) doing with their COOH groups in solution (or in the pure form) - hydrogen bond.  Carboxylic acids do that even in the gas-phase when distilled.  And that is why I was saying that this is all canonical thinking.  Is what is represented in the mechanism what is really going on, or are the other molecules strongly involved (in exchange/bonding) while the reaction takes place.
 * Anyway, it diffuses from the fact, what is written there now is highly contentious, and the rewrite as well - point is that the statement should either be removed, OR properly referenced (all what we are doing at the moment is WP:OR!), or rewritten ánd properly referenced. --Dirk Beetstra T  C 05:28, 14 May 2014 (UTC)
 * This is an example of why I'm insulted when others say that my understanding of chemistry is somehow more flawed that theirs. It may be true, but decency demand it to be justifiable if one dares to make such a public assertion. Plasmic Physics (talk) 00:57, 12 May 2014 (UTC)


 * I repeat my last point. Le Prof  Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)


 * This is just what I expected. The problem is that this chemistry goes beyond the couple of first levels of high school, and may even surpass the first year of a chemistry degree.  People discussing the situation of an isolated acetic acid molecule, Plasmic is even arguing that the ring strain for the 4-membered ring is a factor.  Unfortunately, isolated acetic acid molecules are rather rare (even in gas phase), and here we are talking about liquid phase, where the 'hydrogen bonding' is intermolecular, not intramolecular (that of course still does not mean that one of the C-O bonds has more C=O character and the other C-O-H character - it is a matter of timescale).
 * Anyway, the majority of the reactions of acetic acid are due to its acidity, the formal removal of a proton from the C-O-H fragment. The example that is given in the sentence is a bad one (if one thinks strictly canonical), and in a way I think that whole sentence is bad and should just go.  It is silly to discuss the reactivity of a COOH group in terms of the reactivity of the C=O vs. the C-O-H.  They are chemically inseparable, indistinguishable in terms of reactivity, and thát is what should have been recognised by an experienced chemist.  --Dirk Beetstra T  C 03:40, 12 May 2014 (UTC)


 * As a practiced synthetic organic chemist, I disagree, thoroughly, to the attempts at simplified conclusions absent actual article context. For instance, it is simply too broad and simplistic a generalization to say "majority of the reactions of acetic acid are due to its acidity". Mon Dieu.  mdr. HOAc is acidic because (and here I am falling prey to temptation, and moving too rapidly, and mixing thermodynamic and kinetic aspects of the question) the acidic proton is adjacent an electron deficient center (the carbonyl you marginalize!), and because, entropically, that carbonyl provides a second heteroatom onto which change can be delocalized. Again, this is all so much aimless, near pointless discussion. There are times when PP's point is more valid than not. What matters is the precise text (and pedagogic point), in context , and it does not pay to argue broad ideas and vagaries here.  Le Prof  Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)


 * You made an isolated molecule the topic. "The majority of the reactions of acetic acid are due to its acidity." We could go ad infinitum and debate whether or not they are degenerate, or we could we could replace the sentence with something that mentions types of structural analogues. Plasmic Physics (talk) 04:27, 12 May 2014 (UTC)
 * I used acetic acid as an example, the same is true for benzoic acid or whatever carboxylic acid.
 * That is what you should have been discussing from the beginning (or boldly change it to something more correct, not to something equally incorrect or even less correct - note that saying that the C=O is the reactive group that shows the reactivity with thionyl chloride is confusing: acetone does not undergo a similar reaction (with thionyl chloride, it needs something stronger and forms another type of compound), in ethanol the OH does get replaced with a chloride when reacted with thionyl chloride; and after the change we are discussing here it says that the C=O is more reactive in the COOH group .. ). --Dirk Beetstra T  C 05:15, 12 May 2014 (UTC)
 * It may not be perfectly correct, but at least it the lesser of two evils. Oh, and I did initiate a discussion on the acetic acid talk page. There were no takers. Plasmic Physics (talk) 06:57, 12 May 2014 (UTC)
 * I don’t know how you assess “the majority of the reactions” of a given substance—on the number of known reactions? the most mentioned in papers? the most commonly performed? Anyway, for another bit of dimly remembered trivia, radioactive labelling has shown that in the acid-catalysed dehydration of RCOOH with R'OH to form an ester, RCOOR', the water evolved gets its O from the acid, not the alcohol. In such reactions (nucleophilic substitution?) the mechanism begins with the protonation of the carbonyl oxygen and ends with its deprotonation. It would therefore seem hard to generalize about the relative reactivity of the carboxyl group’s components; it appears to depend a great deal on the reactants & other conditions.—Odysseus 1 4 7  9  07:18, 12 May 2014 (UTC)
 * The lesser of two evils - two wrongs don't make it right, Plasmic Physics. And no takers apparently means that there was no consensus to change either.
 * Regarding Odysseus1479's question, one could do a search of a scientific database of how many papers used reaction A vs. how many used reaction B. However, for a functional group which one could perceive as a combination of 2 functional groups (like here is done for the C=O and the C-O-H in -COOH) is probably impossible or even silly.  --Dirk Beetstra T  C 07:43, 13 May 2014 (UTC)


 * "No takers" means that everyone who had an interest in maintaining the article was apathetic at the time. Any consensus, or lack thereof, can only result from a dialogue. Disagreeing with my opinion that my change was less wrong than the original version is your prerogative, but that does make your opinion factual. Moreover, I gave you a fair chance to discuss the change before it was made; criticising my taking action according to my suggestion is not appropriate if you did not contribute to the decision. Plasmic Physics (talk) 11:49, 13 May 2014 (UTC)
 * Plasmic Physics, you are expecting that all discussion points are taken up in a reasonable time, and that consensus is reached on all of them. If an edit stands, then that edit has an apparent consensus, if then one editor challenges that, that may mean that consensus has changed, but if no-one responded to it, it does not mean that consensus has changed.  If you make a bold-edit, and it gets reverted and discussed, but the discussion either bleeds to death or does not get any further participation, and no consensus is reached, then that does not mean that the bold-edit was right.  And that seems to be a recurring theme with you.  It even doesn't mean that if article A says '1' and article B says '2', that the non-consensus to change it from '1' to '2' in article A should result in a change from '2' to '1' in B (it may even be a WP:POINT violation to do so).  --Dirk Beetstra T  C 05:28, 14 May 2014 (UTC)
 * Yes, I'm expecting that all discussion points are taken up in a reasonable time, because that is what I'm advised by the Wikipedia guidelines. If an editor challenges an edit which was uncontested following a reasonable amount of time, responsibility falls on that editor to open a new discussion before boldly reverting the edit. The edit was not bold, since it was discussed on the talk-page. Plasmic Physics (talk) 08:03, 14 May 2014 (UTC)


 * I encourage you to read WP:CYCLE. This will help you develop a better understanding of the bold-revert-discuss process. Plasmic Physics (talk) 08:17, 14 May 2014 (UTC)
 * '[R]easonable time' is very subjective, anyway, a stale discussion or a discussion that does not move to consensus can be pulled forward with a (bold) edit, but that does not mean that that edit has automatically consensus because the discussion died out, it can still be reverted (with reason) and either consensus needs to be reached, or the edit really does not have consensus and should simply not be performed, or something else could be tried.
 * WP:BRD was exactly what I had in mind: bold edits can come after a discussion died out, or when the discussion did not get to consensus. Anyway, my first reverts for both articles (acid and Cp) were reasoned.  And what you say conflates the issue - one was an undiscussed bold edit, the other was a bold edit which was first discussed, but not gotten to the final.  Both were reverted because someone disagreed (I reverted, Smokefoot already gave his concerns before) .  That means that discussion goes on, and not that the bold edit has to go again, even after the second cycle of discussion has died out.  The issue seems however to be that you do a lot of bold edits which do not have consensus.  --Dirk Beetstra T  C 09:13, 14 May 2014 (UTC)


 * In that case, I shall direct your attention to "BRD is not a valid excuse for reverting good-faith efforts to improve a page simply because you don't like the changes." Plasmic Physics (talk) 10:18, 14 May 2014 (UTC)
 * I did not revert because I don't like it, I reverted because I don't think that they improve Wikipedia, and I certainly think that this needs more discussion and, possibly, another solution. --Dirk Beetstra T  C 11:15, 14 May 2014 (UTC)


 * It comes down to the same thing, disapproving of/disagreeing with an attempt to improve a page. Plasmic Physics (talk) 12:31, 14 May 2014 (UTC)

Unless someone has anything else to add, Q.E.D. Plasmic Physics (talk) 03:45, 19 May 2014 (UTC)

Here we go again with Plasmic Physics - part 2
Plasmic Physics appears to have changed the total focus of Titanium hydride back in October 1st, 2012. Another user is now trying to change it back. The original change was not discussed at Talk:Titanium hydride or in edit summaries. Please take a look at his comment on my talk page, the history of this article and the recent discussion at Talk:Titanium hydride. I am rather busy to get too involved. -- Bduke   (Discussion)  03:37, 25 May 2014 (UTC)


 * ''This foregoing, in its closing, appears to have accomplished nothing it seems, so I will close with a formal proposal:
 * * (i) that all cosignatories consciously return to the principles of WP with respect to these chemistry discussions, including AGF and other policies requiring mutual respect in actions and discussion;
 * * (ii) that PP and all cosignatories herecommit unequivocally to add no substantial chemistry text material without good secondary / tertiary scientific sources—not primary sources, and with sources substantially beyond UG first and second year texts (graduate texts, reviews, and monographs preferred);
 * * (iii) that in selection of chemistry citations, proof-texting be avoided, and instead, a commitment be made to identifying the preponderance of scientific opinion—not via Google, but through reliable scientific search venues such as CAS SciFinder, Pubmed, Thomson Reuters Web of Science, etc.;
 * * (iv) that by all cosignatories, the difference between nomenclature and lexicography discussed above be acknowledged, and through the use of disambiguation, and careful name choice, both familiar and unfamiliar chemical concepts be given adequate definition and coverage in article images and text (whether in same or different articles);
 * * (v) that PP agree to make no gross change to article nomenclature without creating a talk page, prior, and laying out the reasons for the overarching change, and that Talk section be allowed to stand for two weeks before a bold, comprehensive nomenclature edit is made;
 * * (vi) that for any article for which PP can reasonably be aware that the cosignatories of this long discussion have interest or past involvement, that the same "discuss first" rule be again adhered to for any major edit, or series of minor edits that taken together constitute a significant change to the article text (given the clear differences of opinion about approach to practical editing that this page lays bare); in such cases, the same let Talk stand for two weeks criteria be applied;
 * * (vii) that on becoming aware of the indicated Talk sections, that the cosignatories of the foregoing long discussions agree to approach matters civilly, with both sides committed to the careful thorough conversation as eventually was seen in the foregoing discussion;
 * * (viii) that when a no point of consensus is soon reached in these Talk venues, all cosignatories here agree to seek additional participants to weigh both sides of the issue, in the specific context (and I will volunteer evening time for this if I am available); all then agree to abide by the consensus that is eventually reached (e.g., and if in the minority, not return again after a pause, to attempt to subvert consensus);
 * * (ix) that all cosignatories here agree, whether for edits covered above or otherwise, that on experience of first reversion of an edit, to move the matter immediately to Talk, and allow the initial, more longstanding text to remain in place, while discussion takes place over the aim of the once-reverted edits (where points vii and viii again apply); and
 * * (x) that all take seriously their own intellectual limitations, and respect the need for stable article spaces, and accept that return to earlier business-as-usual approaches to get edits in place may result in a block of work in this Project.


 * Bottom line: Can we not overly dissect, this, but instead, all agree to abide by it? I have heart remaining for about ten more minutes of this, and then, no more.  Le Prof  Leprof 7272 (talk) 20:10, 29 May 2014 (UTC)
 * Well Leprof 7272 you have certainly made a big effort to respond to many of the points raised. Our discussion did stray off the initially raised topic and into a couple of specific changes made by PP. And some of that discussion should take place on the article talk pages.  Some of us have a problem with (ii), but I agree if there is a dispute about a fact then we should consult the good non-primary sources. But I support your points i and iii-x. Graeme Bartlett (talk) 21:29, 29 May 2014 (UTC)
 * Graeme, ty for replying, and perhaps be prepared to reword (ii), as is necessary, to make it more broadly acceptable. Le Prof  Leprof 7272 (talk) 05:38, 1 June 2014 (UTC)
 * Although I do not agree with the interpretation of my remarks (but that may be in my wording; I am not responding to the points individually, how vehemently I disagree with how Leprof 7272 interpreted them - I think we basically agree, Leprof 7272), I do think that what User:Leprof 7272 has been suggesting is basically what we all would expect from editors in the first place. --Dirk Beetstra T  C 03:47, 1 June 2014 (UTC)
 * I think we do and will agree quite more than you might think DB. But, ignoring the chem matters (which can be settled at actual articles)—it seems you are agreeing with the thrust of the proposal? If so, and if PP does not respond, I will leave it to you how to take this forward.  My view is that if something is not formalised as a result of this discussion, first here, and if necessary at an administrative board, then the behaviour and argument will recur (see Bduke above, re TiH2). This will create further confusion and waste further time in article editing, and will eventually result in lost tempers and emotion-fueled bans/blocks against PP (as almost happened here), that will just set up conflict long-term. The proposal wording was carefully chosen, as you and Graeme both surmise, to make the point that what is being asked is what all should be able to agree to, generally. And with respect to past issues with PP, it is solid enough [see (v) and (vi)], that if it is flouted, it can then be taken immediately back to Admins, for the block or ban originally requested. The only grant being really asked of you is implied in (iv), and that is that the -yl radical find a home somewhere—but the details of this can and should be left for later, to the actual articles and talk pages, where you can still fight to see your important perspectives heard.  Bottom line, can the foregoing be asked of PP, to forestall another round of this, if he seeks at some point to redirect articles without consensus?  Cheers.  Le Prof  Leprof 7272 (talk) 05:38, 1 June 2014 (UTC)
 * Long proposals such as the text at 20:10, 29 May 2014 above are generally unsatisfactory at Wikipedia because there are too many details to argue about, and because an uninvolved admin would have a great deal of trouble determining whether a particular clause had been breached (bearing in mind WP:AGF and WP:BOLD). The actual problem is that one editor is not working collaboratively and is causing disruption, and experience from other cases shows that ongoing problems may still occur even if all clauses in the proposal are followed. This project does not have the power to sanction an editor, and unless clear evidence that is understandable by third parties is available, an admin noticeboard is unlikely to help. If no rogue admin is available (John—do you want a challenge?), an WP:RFC/U may be necessary. If good evidence and discussion occurs in an RFC, with a solid consensus that there is a problem, any ongoing problems would be likely to result in a topic ban at an admin noticeboard. That would involve a lot more time wasting I'm afraid. Johnuniq (talk) 06:55, 1 June 2014 (UTC)
 * - the thrust of the proposal is basically what the policies and guidelines of Wikipedia suggest, and what has been suggested over and over. It has however been bringing us here with Plasmic Physics on a regular basis.  What brings us here were not the 2 specific cases, what brings us here is how Plasmic Physics was solving the, real, situations that 'cyclopentadienyl' and 'the COOH-functionality' represented (and similarly, titanium hydride and mercury hydride, and earlier situations with categorisation of alkenes and naming conventions).  I don't disagree that there are issues as things were standing (he does correctly 'attack' problematic cases), I don't disagree that there are solutions or whether things should be covered (we do need to cover the cyclopentadienyl radical), the basic issue is how solutions are implemented, and which solution is implemented [by Plasmic Physics] - that, again and again, is bringing the controversy here.  --Dirk Beetstra T  C 07:41, 1 June 2014 (UTC)

I can agree to proposals i to x, except for ii and vi. My reasons: while ideal, it is not possible in all cases, e.g. for some articles there simply do not exist secondary sources; it is rarely if ever known which articles are covered by vi, moreover, this is complicated by WP:HOUNDING. Plasmic Physics (talk) 07:39, 1 June 2014 (UTC)


 * I can have a look. What do you guys see as the problem? What do you all see as a workable realistic outcome from this? --John (talk) 10:43, 1 June 2014 (UTC)
 * - the problem is quite convoluted. One of the problems is the total change-over of long-standing articles (changing subject; see cyclopentadienyl, titanium hydride, mercury hydride) without prior discussion (or, if discussion was initiated and dies out, boldly implementing a solution where there is maybe no opposition, but also no support for overturning the current version).  But naming conventions etc. are also part of the issue (part of a currently active restriction on Plasmic Physics), as is sometimes a too 'canonical' way of thinking (putting aromatics in cycloalkene categories, -COOH-group discussion above).  --Dirk Beetstra T  C 12:09, 1 June 2014 (UTC)
 * I see. Yes, I read some of the discussions and the -COOH discussion was interesting. If I get involved here, do you think you need an experienced editor's opinion, or admin action? I can do either. --John (talk) 17:39, 1 June 2014 (UTC)
 * John, at this stage, I think what is needed, is Admin guidance, if not action, see following.


 * The fact that PP will not agree to point (ii) for the reason stated, is not an issue. Of course, if a bit of text is not yet supported by monographs or reviews, yet reflects the preponderance of scientific opinion—e.g., as seen by its appearing repeatedly in primary source article introductions—it is certainly acceptable; what is prohibited for WP editors is our determining from a primary source or the data whether something is true or not, our determining from these what is important or not. (The Flippin-Lodge angle concept appeared for years only in primary sources citing the original Clayton Heathcock articles, apart from a single Aldrichimica Acta review; but the concept was broadly recognized through all of these primary article citations as an accepted concept (long before the book sections and chapters began to appear).  So on this point, PP, cheers, fine.


 * However, here is the rub, as I see it. PP is not always wrong about the chemistry (though he sometimes is, in emphasis or fact, as we all are). He has, however, shown a pattern of practices that seem to be attempts at end-arounds of community perspective—knowing from past discussion that his edits will not achieve consensus, but doing them anyway, or worse, as Dirk notes, "if discussion was initiated and dies out, boldly implementing [his] solution…" (despite the fact that the discussion did not yield that consensus). It was for this reason I proposed points (v) and (vi), above.


 * It seems that PP is willing to assent to (v), about not commandeering articles to institute broad changes in keeping with his singular perspectives on nomenclature. He appears unwilling, however, to assent to (vi), that is, to try to anticipate possible occasions of community opposition, despite the clear patterns of conflict in his interactions here with other chem editors. His excuses for not being willing, as (vi) asks, to pre-post at Talk at articles where he anticipates there might be opposition, are:
 * How can I possibly know? Ans., check Talk for familiar opponents, something that takes all of 60 secs., and then consult your prior experience—e.g., knowing that a further foray into metal hydrides, or aromatics as cycloalkenes, or common OChem functional group analysis from a PChem perspective are very likely to cause problems.
 * I say no, because to say yes is to allow my being hounded. Ans. It is not hounding for experienced editors to keep tabs on specific other editors who have displayed a pattern of naive, or otherwise problematic edits, or other behaviour which is problematic at Wikipedia. (I have several who do this with my every edit, hoping to show up Le Prof. It is their freedom. I just laugh.)


 * Bottom line for me, first, PP's continuing unwillingness to agree to reasonable restraints on his behaviour is problematic, and suggests the issues and conflicts will continue to occur. Second, many of his perspectives, from this professional chemist's perspective, are decidedly naive. If three others concur that we are arguing against a naive opinion, we cannot be expected to individually take this or any editor from an undergraduate perspective to a depth of understanding gained from further decades of teaching or research. No, if a consensus about article content exists, the argument is over, even if it is against him. What we have to expect from him, esp. given the further disciplinary consensus that appears here as to the problems he causes, is that he bring a greater modicum of humility to his editing, allowing that he does not have the right to redirect entire articles based on a hunch that he understands it better than the rest of the community, or that his way of expressing a subject should be what appears. Even if his confidence did not considerably outpace his real understanding, he could not expect to subvert consensus, expressed or anticipated.


 * Because he is unwilling to accept the need to work toward consensus, I now propose he limit his editing to nanotechnology, and not to any area of general, organic, inorganic, organometallic, or other chemical specialty (for which he has even more limited experience than his major coursework). I did not come in to this, in favor of any restriction on his editing, but now I am.  Le Prof  Leprof 7272 (talk) 22:35, 1 June 2014 (UTC)


 * You misunderstand, many articles to which I have made problematic edits, only gains interest or attention as a result of hounding. I can agree to vi, when issues pertaining to it has been resolved. Progress has been made, in that a category of article types has been established. Plasmic Physics (talk) 00:08, 2 June 2014 (UTC)
 * "hounding" ? Please explain what you mean. I see no hounding. -- Bduke   (Discussion)  00:54, 2 June 2014 (UTC)
 * "Wikihounding is the singling out of one or more editors, and joining discussions on multiple pages or topics they may edit or multiple debates where they contribute, in order to repeatedly confront or inhibit their work. This is with an apparent aim of creating irritation, annoyance or distress to the other editor. Wikihounding usually involves following the target from place to place on Wikipedia." The main belligerent is Smokefoot, I suspect there may be others, however they are not so wholly committed and so are the more difficult to identify. Plasmic Physics (talk) 01:04, 2 June 2014 (UTC)
 * What nonsense. Smokefoot is doing nothing of the kind. It is you who are irritating a lot of editors of chemistry articles and not learning from the criticism that comes from several editors. I am beginning to agree with Le prof.-- Bduke   (Discussion)  02:54, 2 June 2014 (UTC)
 * PP, first, it is entirely feasible for you to accept point (vi), without further argument. You need just [a] check the Talk page in new articles that you intend to edit, for the interest of others who have been critical of your history of chemical editing, and [b] when beginning to edit at such a page in their spheres of influx, post a prior Talk page explaining what you intend. That is, plan for, think about, and communicate what you intend to edit, before you act. See for instance:, and Talk sections thereafter. At this page, I have had contentious relations with a fellow editor, and so I pre-post every edit I intend to make, so if he should so care, he can pipe in and argue it. I am not asking anything of you that I myself do not do in similar situations. Now, will you or will you not accept this guidance?


 * Second, your arguing the hounding matter needs to cease. If and when someone "hounds" you in future, create a clear, recent, substantial record of it, and take it to the Admin pages. There, cite the specific part of the WP policies you think are being violated. Your arguments here, communicating your recollections of policies—they will not reverse the fact that the consensus here is that no one is hounding you.  Accept this consensus, stop wasting time (or pursue the separate formal complaint, elsewhere). Your rejection of (vi) for reasons of what are, at best, a loose, and informally leveled counter-accusation simply is immaterial here. Will you or will you not accept constraints (v) and (vi) going forward? The alternative: next hint of an issue, I will stop defending you—for reasons of due process, or otherwise—and will join the call for your being formally limited in your editing. Le Prof Leprof 7272 (talk) 03:22, 2 June 2014 (UTC)


 * Indeed, the hounding accusation is nonsense. IF (and I say if) someone is following you around checking your edits, then the sole reason for that is that it is needed, because every time your edits are being discussed it turns out that what you were doing is, at least, controversial (and when looking back often other edits show up that turn out to be controversial (the Titanium hydride changeover was noticed 1 1/2 year after the fact - if it was hounding, those would have come out immediately).  It might be hounding if the editors would report you for non-issues.  --Dirk Beetstra T  C 03:30, 2 June 2014 (UTC)


 * To validate me accepting vi, please give case where vi would retrospectively apply, where there has been previous invested interest by another user of the project. Why do I need to cease arguing the hounding matter? I don't care enough to bring it to the Admin pages. How can anyone justifiably decide whether I've been hounded or not, without so much as a shred of evidence either for or against? Regardless, a verdict does not help in solving the issue of handling cases where interest in an edited article has been gained for the wrong reasons, frustrating vi. Plasmic Physics (talk) 04:51, 2 June 2014 (UTC)
 * Do you understand that targeting me personally with clause vi, is akin to accusing me of not having abided up to now? That is why I take issue, and require justification. Plasmic Physics (talk) 04:55, 2 June 2014 (UTC)
 * Plasmic Physics, this is not a court of law and we will gain nothing in talking about hounding. If there's a consensus here that your editing should be limited, then arguably that would be binding. Do you see any down side in accepting the proposal that your edits here should be bound by consensus, the same rule we should all be following anyway? --John (talk) 23:47, 2 June 2014 (UTC)


 * I totally agree, I'm not interested in discussing hounding, but instead how to take its supposed existence into consideration when negotiating clause vi. No, I don't see any downside to being bound by consensus. Plasmic Physics (talk) 02:35, 3 June 2014 (UTC)


 * OK, thanks for that. I don't see any obstacle to agreeing the principles at the top of this. Are you worried people will use them against you? If you sign up, I will make sure that doesn't happen. I can tell you are an intelligent and well-meaning editor but it sometimes happens that intelligent and well-meaning people disagree. It looks like you have disagreed with a whole lot of people here. If you sign up to something voluntarily it will be a lot smoother and easier than if we have to go through the palaver of having a wider community discussion at one of the boards. It's up to you of course. --John (talk) 07:00, 3 June 2014 (UTC)


 * Fine, I suppose we can postpone resolution of the issues which I have raised, to a later date. After all, the proposal is not set in concrete. I don't take to shooting first and asking questions later, hence my reluctance. That said, I agree to attempt a strict adherence to clauses i, iii-v, and vii-x contained within the above proposal; and where possible, to clauses ii, vi; subject to future consideration and amendment. Plasmic Physics (talk) 09:31, 3 June 2014 (UTC)
 * I would also like to have an xith clause added, that calls for a restoration of civility - that disgruntled users not make a mountain out of a molehill by automatically raising every single issue before the Project, before attempting a BRD cycle. Plasmic Physics (talk) 09:40, 3 June 2014 (UTC)
 * It would be appreciated if someone would acknowledge with a response. Plasmic Physics (talk) 12:17, 4 June 2014 (UTC)
 * I acknowledge your response, and I appreciate it to some degree, but I am a little perplexed. If I understood correctly, the terms you have agreed to alter the normal "BRD cycle" in your case. I think therefore your previous response is difficult to parse. I certainly agree that people ought to be civil. Do you think anyone has been uncivil to you? --John (talk) 15:28, 4 June 2014 (UTC)
 * How do you suppose my terms alter the cycle? Yes, I think someone has been uncivil, but who that is, is besides the point. Plasmic Physics (talk) 22:39, 4 June 2014 (UTC)
 * Because some of the terms you have agreed modify or extend the normal editing cycle. for example, is not a usual requirement for editing. I think it is for the good though, and I will help make sure that nobody is uncivil or gives the impression they are hounding you, if you unequivocally accept them. Do you? --John (talk) 20:42, 5 June 2014 (UTC)

Proposed solution
I'll summarise the proposal as I see it more succinctly. User:Plasmic Physics will seek consensus using high quality sources before making any changes to chemistry-related articles which might be seen as controversial. If in doubt, assume it is controversial. I will enforce this with warnings and blocks if necessary. I will also mentor PP and suggest ways that he can edit more productively. I will also enforce the highest level of politeness and collegiality in other editors dealing with PP. This too I will enforce with warnings and blocks if necessary. My aim going into this would be to enable harmonious and productive editing from all involved and to keep admin action to an absolute minimum. Full disclosure: I am a Chemistry graduate and educator with many years' experience. I recently worked with others, especially User:Sandbh, to get our metalloid article to FA class. I do not think this degree of involvement rules me out from making this offer. If anybody does, please feel free to state it and I will consider withdrawing. Please indicate below if you accept this. --John (talk) 21:06, 5 June 2014 (UTC)

Signups

 * 21:08, 5 June 2014 (UTC)
 * 23:35, 5 June 2014 (UTC)
 * 08:15, 6 June 2014 (UTC)
 * 12:21, 6 June 2014 (UTC)
 * 08:56, 7 June 2014 (UTC)
 * Dirk Beetstra T C 03:41, 8 June 2014 (UTC)
 * 09:35, 8 June 2014 (UTC)
 * Bravo, John, and apologies to all for my respite. Glad to see this come to a productive conclusion, where it is on PP's shoulders to restore full trust. Cheers, PP, and call on me if you want stern pre-editorial advice. Leprof 7272 (talk) 01:23, 15 June 2014 (UTC)

Discussion

 * Ok, with no objections and plenty of sign ups I will take this on as described above. Please, anyone who sees anything they think I may have missed, just ping me. --John (talk) 23:26, 20 June 2014 (UTC)

Calling all cars
Still need Ochemists, biochemists, etc. with natural products expertise to tune into the Natural products article. Things are beginning to move again, and are more peaceful, but secondary source-wielding experts still desperately needed. (Where "god" stands for "grumpy old doc".) Le Prof Leprof 7272 (talk) 05:12, 21 June 2014 (UTC)

After 5 yrs unnoticed
... and people possibly being misdirected, removed "Nor-" from Template:Orgchemsuffixes, because it does not mean "no residue". See Nor-. Le Prof Leprof 7272 (talk) 05:05, 21 June 2014 (UTC)
 * You keep me puzzled on why someone should wait ten years before using knowledge. . -DePiep (talk) 12:53, 22 June 2014 (UTC)

Discussion on providing detailed synthetic schemes in articles at the Medicine project page
I've started a discussion over on the Medicine Project page about the inclusion of detailed synthetic routes in articles. I apologize for not posting here earlier and now realize that this page was probably the most appropriate forum for the discussion. Please accept my belated effort to correct this mistake.

As you will see there, I am concerned about the recent proliferation of very detailed synthetic schemes for in many pharmaceutical drug articles. Although a PhD synthetic/medicinal chemist myself, I am concerned that these very detailed routes are 1) incomprehensible, and 2) of little interest to the vast majority of our readers. As a third point, the synthetic routes being added seem in many cases to be arbitrarily chosen from among the dozens of different routes available in the literature, and thus lack notability.

It is not my intent here to trivialize the importance of chemistry or the value of synthetic expertise, as synthetic chemistry is in fact my own vocation. Please take a look and offer your comments. I suspect there will be some disagreement/opposition, but if you have any ideas on how to address the concerns I have raised it would be very much appreciated. I'm not looking to drive an agenda here, just to figure out a mutually acceptable way to address what I see as an issue of keeping the level of the science appropriate to our audience. Formerly 98 (talk) 13:18, 22 June 2014 (UTC)