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Wikipedia:Featured article candidates/Acid dissociation constant/archive1

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The following is an archived discussion of a featured article nomination. Please do not modify it. Subsequent comments should be made on the article's talk page or in Wikipedia talk:Featured article candidates. No further edits should be made to this page.

The article was not promoted by User:SandyGeorgia 23:04, 25 October 2008 [1].

Acid dissociation constant

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Nominator(s): Petergans (talk)


The concept acid dissociation constant is of major importance in chemistry, physics, earth sciences (including environmental sciences) and biology (including human biology) and is also important in other areas such as the development of new pharmaceuticals and all sorts of industrial processes where acidity has to be controlled. The article presents a comprehensive coverage of the topic and indicates the main areas of application. It should therefore be of interest to a wide range of the readership.

The topic is covered, at an elementary level, in all text-books on general chemistry, though the treatment is usually simplified. The simplifications are explained in this article.

I have been active in research in this subject area since 1972. Our programs Hyperquad are the world market leaders for the determination of acid dissociation constants and stability constants of metal complexes with ligand acids. Correspondence with users of this software has given me an appreciation of the range of applications of interest in research today. This is reflected in the structure of the article.

I am confident that if this article is accepted for featured status that it will enhance the reputation of Wikipedia among scientists and science students.

Petergans (talk) 09:21, 9 October 2008 (UTC)[reply]

Comments

This is a source of data, not of the article content. I believe the data to have been reliably taken from the literature. Petergans (talk) 15:39, 9 October 2008 (UTC)[reply]
I"m not sure what exactly you mean by "source of data, not of the article content", do you mean that it's not used as a source? If it's not used as a source, why is it in a footnote? If it's being used as a source for data in the article, then it needs to be reliable. Ealdgyth - Talk 16:21, 9 October 2008 (UTC)[reply]
Sorry I did not make myself clear. It is an comprehensive source of numerical data, that is, numerical values of acid dissociation constants, the title entity of this article. As such, I prefer to reference it directly in the relevant place in the article rather than list it in external links, but I'll move the reference there if Wiki style demands it.
Regarding reliability, http://www.chem.wisc.edu/areas/reich/pkatable/index.htm gives access to a list of the 64 references to the primary literature from which the data were extracted; the current link is more general and has a link to that page. Petergans (talk) 08:56, 10 October 2008 (UTC)[reply]
Otherwise, sources look okay, links checked out with the link checker tool. Ealdgyth - Talk 14:06, 9 October 2008 (UTC)[reply]
Currently Leaning Oppose I really appreciate the editors/nominator of this article for working on this article and bringing it up to to its current quality. I see that it has been the recipient of nontrivial amounts of thought and elbow grease... I'm seeing two things that concern me: first, the article is a bit beyond the reach of the uninformed reader [insert arguments <here> that uninformed readers won't be examining this article anyhow]. In the first sentence of the WP:LEAD there are already blue links that lead to other articles; I'd have to read those before I could continue on with this one. A WP:LEAD is supposed to function as a stand-alone intro/summary of the article... The article, especially the lead, needs to make an attempt to address a more elementary-level reader.. although it's fine to retain info that is beyond that level in later sections. Second, I'm really not getting a concrete feel of the reasons for its importance. After searching about 3 or 4 minutes I found this book (just the first interesting one I ran across): "Risk Assessment of Chemicals" By C. J. van Leeuwen, Joop L. M. Hermens.. it says "To neglect the chemicals' dissociation may lead to serious misjudgment of their hazard.. " on p. 254. Now that's a real-world fact I can hang onto. I'd like to see more such. Ling.Nut (talk—WP:3IAR) 10:15, 10 October 2008 (UTC)[reply]

The first line of the lead reads "An acid dissociation constant (aka acidity constant, acid-ionization constant) is an equilibrium constant for the dissociation of an acid". If the reader does not already have some grasp of the linked concepts, then I suspect the article will be completely unintelligible to him/her. The links put these concepts on a more rigorous basis. The need to address a more elementary-level reader is a recurrent theme for technical articles like this one and it is difficult to resolve. We have pitched the intro level towards a school student studying chemistry and coming across this idea for the first time.

I take the point about risk assessment and will insert something about it in the importance section. Petergans (talk) 14:45, 10 October 2008 (UTC)[reply]

  • Please have a look at this link which suggests possible wikilinks for the article. Note that some terms may already have been wikilinked previously in the article, and also that any new wikilinks should typically be double-checked to make sure they are relevant to the article (though for specialized, technical terms it is far less likely that the suggested link is irrelevant. Choose carefully; no real reason you have to add any of the suggested links if they don't appear to add value to the article.
  • "Biochemistry Primer for Exercise Science" by Michael E. Houston (p. 5) states: "The stronger the acid (HA), the more it is dissociated, and the higher the concentration of the conjugate base (A-). Therefore, the larger the numerical value for Ka, the stronger the acid." That last sentence in particular is crystal clear. Our article says (what I believe is) the same thing in a different manner: the larger the value of pKa, the weaker the acid .. but this article is explicitly about Ka. I understand the easy relationship etc. (very roughly, of course), but I think we should couch our explanations in terms of the explicit topic of the article... Ling.Nut (talk—WP:3IAR) 17:53, 10 October 2008 (UTC)[reply]

There is a problem here: in common usage the terms "pKa" and "acid dissociation constant" are used (wrongly!) almost interchangably. I think that we would have to say something along the lines of - the stronger the acid the larger the values of Ka and the smaller the value of pKa - but to me this sounds a bit confusing. In practice pKa values are used much more often than Ka values, but I don't see how this can be reflected in the article title. Petergans (talk) 18:45, 10 October 2008 (UTC)[reply]

  • Houston (see above) states in his Glossary (p. 245) that 'Ka "describes the ability of an acid to donate a proton". This is a restatement of the observation (above) to the effect that "larger 'Ka = stronger acid", since an acid is apparently a compound that can donate a proton. I can see why you would skip this, since we are unpacking the defition of "acid" here. But really, I think we actually can unpack these things, at least in the lead, without any damage to the article as a whole. I hope you'll understand that my intention is not to dumb-down the article; just to make the WP:LEAD a bit more stand-alone. I understand your stance that the reader must have "some grasp of the linked concepts" (to quote, not to scare-quote). But... the higher the number of elegantly-expressed ideas (some appearing as blue wikilinks) in the lead, the less stand-alone the lead is... thanks Ling.Nut (talk—WP:3IAR) 18:14, 10 October 2008 (UTC)[reply]

These are very helpful comments, thank you very much. I shall be away for the next two weeks so I will get round to dealing with them and others that will come in when I return. Petergans (talk) 18:45, 10 October 2008 (UTC)[reply]

Nominators are expected to address issues promptly; if you can't get to this for several weeks, I suggest withdrawal. Also, there are numerous WP:ACCESS issues. SandyGeorgia (Talk) 22:21, 10 October 2008 (UTC)[reply]
Please be more specific about the access issues. I will try to answer them while on holiday. Petergans (talk) 09:06, 11 October 2008 (UTC)[reply]

As a Chemistry Education major, though not an expert by any means (precipitates is one of my weaker areas), all the major problems I see can be summarized into three arguments:

  • The article addresses Ka in theory but lacks information of it in practice (i.e. experimental determinations of Ka including lab methods, (answer below Petergans (talk) 08:53, 11 October 2008 (UTC)) notable historic milestones and contributors, and applications to industry). Even the "Importance of pKa values" section which addresses applications to industry remains vague as to specific examples of its usage (i.e. stating that acid disassociation values are used to increase blood absorption of pharmaceuticals but failing to detail an example of a drug that has been adjusted due to this...yes I know that there are copyrights on new drugs but maybe an old one like Aspirin pills).[reply]

This user does not appear to have read the article properly; there is a complete section entitled Experimental determination of pKa values with a link to a more detailed article Determination of equilibrium constants. Petergans (talk) 08:53, 11 October 2008 (UTC)[reply]

Egg on my face. I scanned quickly through the article. The lack of comprehensiveness required by Wikipedia:Featured article criteria still stands though; the applications section lacks specific examples of its usage. This leads me to the appropriate structure requirement of the featured article criteria. Why is this critical aspect of the acid disassociation constant so far from the lead?--Jorfer (talk) 21:37, 11 October 2008 (UTC)[reply]
Also having a link to a more comprehensive article does not allow you to be this vague on such an important point in the Summary: "The buffer regions carry the information necessary to get the pKa values as the concentrations of acid and conjugate base change along a buffer region." --Jorfer (talk) 22:00, 11 October 2008 (UTC)[reply]
  • The article does not use the simplest and most artful language to communicate ideas. An example of this would be my explanation (above) of what the "example" in the "pharmacology" section was trying to say (which I believe would suffice).

The details are in Avdeef's book, reference 42. Petergans (talk) 08:53, 11 October 2008 (UTC)[reply]

Have you read Wikipedia:Featured article criteria where it says the article must be well-written. The point is one example of the article not being well-writen.--Jorfer (talk) 21:22, 11 October 2008 (UTC)[reply]
  • It does an insufficient job of explaining to the most likely readers of the subject (high school and college students trying to pass Chemisty class) how the equations actually work. It gives the equations and expects the reader to understand how they work. Several examples of real Ka problems (with explanations) would be most effective in breeding understanding of the subject matter.--Jorfer (talk) 00:41, 11 October 2008 (UTC)[reply]

I don't understand this comment. There are many examples showing how the concept of pKa can be applied to derive useful information. Petergans (talk) 08:53, 11 October 2008 (UTC)[reply]

Lead-in

I've modified it in the light of comments. Does it need further work? Petergans (talk) 11:05, 11 October 2008 (UTC)[reply]

Yes, that's clearly a step in the right direction. I hope to be more specific later; now I need to grade freshmen essays. Wish me luck :-). Ling.Nut (talk—WP:3IAR) 11:40, 11 October 2008 (UTC)[reply]
hazards

Added the reference and an example at acid dissociation constant #Importance of pKa values

  • Is there some authoritative source that prefers one term over the other? Or is there some other strong reason to do a page move? "Acidity constant" is already a redirect, and is already mentioned in the first few words of the lead... Ling.Nut (talk—WP:3IAR) 02:48, 13 October 2008 (UTC)[reply]
  • I'm a chemist and I often call it "dissociation constant" (the "acid" often being implied by the context), and rarely "acidity constant". But truth be told, like many chemists I'm lazy and normally just use "pKa" or "Ka". A Google Books search shows slightly more hits for "acid dissociation constant" than for "acidity constant" (780 vs 683). I prefer "acid dissociation constant" because it makes explicit what the process it represents is, while "acidity constant" could be ambiguous because some people prefer to work with formation constants (the reciprocal of the dissociation constant). The only thing I see in favor of acidity constant is that it is listed in the IUPAC Compendium of Chemical Terminology. --Itub (talk) 05:34, 14 October 2008 (UTC)[reply]
  • All my high school and college chemisty classes have used acid disassociation constant when not referring to it simply as Ka (this includes the books and lectures). I actually have never heard the term acidity constant used.--Jorfer (talk) 14:33, 14 October 2008 (UTC)[reply]
  • I was personally not 100% convinced of my arguments, but I believe that the IUPAC's goldbook is the biggest authority you could get in this field. If IUPAC would use the term "actinoid" if you were to submit the article to FAC would you sue the term "actinide" because more people use/know it? Nergaal (talk) 03:20, 17 October 2008 (UTC)[reply]

The title "Acid dissociation constant" accurately describes the content of the article, whereas "Acidity constant" is meaningful only in a specific context which identifies it as a dissociation constant. Petergans (talk) 13:49, 17 October 2008 (UTC)[reply]


  • Support (Disclaimer: I contributed to this article mostly with style issues and with suggestions, but did not add much content myself.) This is a very comprehensive encyclopedic article on this topic, which goes well beyond the usual introductory textbook treatments. I agree that anything that can be done to make the lead more accessible is helpful, but it is unrealistic to ask that this article be a stand-alone teaching resource about acid-base chemistry. First, because this article is just about one aspect of acid-base chemistry, the dissociation constant, which cannot be understood without knowing the basics about concentrations, activities, free energy, chemical equilibrium, acids and bases, and chemical bonding. Nevertheless, the article does make an effort at explaining some of these related topics but cannot be expected to teach them from scratch.

    Remember that Wikipedia is not a textbook: "Wikipedia is an encyclopedic reference, not a textbook. The purpose of Wikipedia is to present facts, not to teach subject matter. It is not appropriate to create or edit articles that read as textbooks, with leading questions and systematic problem solutions as examples. These belong on our sister projects Wikibooks and Wikisource. Other kinds of examples, specifically those intended to inform rather than to instruct, may be appropriate for inclusion in a Wikipedia article."

    As I see it, the difference between a textbook and an encyclopedia article is that while the encyclopedia hopes to "tell the whole truth" about one topic, the textbook has much more space, can start from the basics, teach concepts in a sequence that is useful for learning, can include plenty of examples and even exercises, and can hide some of the ugly facts that are not essential for an introduction. Some may complain that this article is just useful if the reader already knows about the topic. That may be true, but this is acceptable IMHO because an encyclopedia is a reference work. Those who really know nothing about chemistry will be much better served by reading a general chemistry textbook. --Itub (talk) 07:56, 13 October 2008 (UTC)[reply]

Comments. I have little knowledge of chemistry so please excuse any misreadings based on ignorance. I am assuming that a reader of this article would be expected to have some prior knowledge of modern chemistry, since this is not the first article a novice would look at. With that in mind, here are some thoughts.

I will post notes section by section, since it will probably take me a day or three to get through the article. These first notes are all from the definitions section.

  • I found the sequence of three equations in the definitions section on conjugate bases quite confusing to read. I wrote a long description of my confusion and then deleted it because in writing the notes I started to understand it, but I think something could be done to clarify the way this is presented. If I understand it correctly, the sentence that says "The conjugate acid of a base, B, "dissociates" according to" is followed by an equation in which the conjugate acid, BH+, plays the role of "acid", not conjugate acid, in the equation "acid + base = conjugate base + conjugate acid", which you give earlier as the template. That's very confusing! You are, rightly I think, keeping that equation as a template and making everything fit it, but because you don't say so the "conjugate acid" is misleading. Perhaps if the sentence read something like "The conjugate acid, BH+, of a base, B, "dissociates", taking the role of the acid in equation (1) above", or some similar means of referring to the template equation.

I'm on holiday in Crete, but here are some quick answers.Petergans (talk) 14:38, 20 October 2008 (UTC) A general point: "reference to equation (1) above" would be fine if all the equations were numbered as they would be in a paper published in a chemical journal. Unfortunately, it is not normal practice to number equations in WP, where a more discursive style is preferred. Some guidance on numbering of equations would be welcome. Petergans (talk) 08:18, 25 October 2008 (UTC)[reply]

In Lowry-Bronsted theory every acid has a conjugate base and every base has a conjugate acid. It is therefore to some extent arbitrary which partner is denoted as conjugate. But you are right, some clarification is needed. Petergans (talk) 14:38, 20 October 2008 (UTC)[reply]

The new version makes this much clearer. Mike Christie (talk) 23:03, 25 October 2008 (UTC)[reply]
  • "In fact the bicarbonate ion is amphiprotic": "amphiprotic is linked, but in a context where you're explaining the nature of proton exchange to a reader who presumably is not yet familiar with it, the comment seems unhelpful: such a reader would not understand the word and would have to click on the link. I'd suggest either adding the definition: "the bicarbonate ion is amphiprotic, meaning that it can either donate or receive a proton", or else eliminate the word "amphiprotic" completely -- you don't use it in the rest of the article.
  • "a "proton" is understood to mean a solvated hydrogen ion"; perhaps link "solvated" to solvation?
  • The article on Hydronium asserts that "hydronium" is an obsolete name; is that correct? If so, would it be better not to use the term?

The definitions section has been modified in the light of these comments. Petergans (talk) 09:27, 25 October 2008 (UTC)[reply]

  • In the "Equilibrium constant" section: the "hydration of the proton can also be assumed to be constant" appears to be the reason why the term "[H3O+]" turns into "[H+]" when we move from Kt to Ka. If this would be clear to a chemistry student, I'll take your word for it, but I don't follow it. If the concentration of H3O+ is constant (presumably true if the hydration of the proton is constant) then why is the term still there at all? If the term H+ is not constant, doesn't that mean that the hydration of the proton is not constant? What am I missing here?

Hydration means the addition of water; it is the concentration of water which is constant. Will attempt a clarification next week. Petergans (talk) 14:38, 20 October 2008 (UTC)[reply]

  • In the section on monoprotic acids you have both "half-neutralization" and "half neutralization" in the same sentence; I don't know which is preferable, but the article should be consistent.
  • In the sentence "Any base with a pKa value larger than the upper limit is "fully" de-protonated at all attainable pH values", why are there quotes around "fully"?

It is common practice to use the term "fully dissociated" when in fact the the difference from 100% dissociation is finite, but very small. See hydrochloric acid below. Petergans (talk) 14:38, 20 October 2008 (UTC)[reply]

I thought that might be the explanation. I think a better way to indicate this to the reader is needed than just quoting "fully", though. Mike Christie (talk)
  • The following sentence is "This is known as solvent leveling"; it's not clear to me what this refers to. The previous sentences described the characteristics an acid would have if its pKa were below -2, and similarly for a base with pKa over 12. Those characteristics are solvent leveling? Do you mean that (essentially) complete dissociation or de-protonation are referred to as solvent leveling?

This is a subtle point that needs attention. The phenomenon is that in a given solvent all acids with pK less than a certain value are classed as strong acids, hence they are brought to the same level of strength. In another solvent a particular acid may be weak or vice versa. Likewise all bases with a pK value greater than a certain value are classed as strong bases. Petergans (talk) 14:38, 20 October 2008 (UTC)[reply]

I think I follow you. A version of this explanation in the article would be good. Let me see if I can rephrase what you said to see if I have it right: all acids with pK less than -2 are essentially fully dissociated have the same strength at pH 0; hence the differences in pK do not lead to a difference in pH. A similar statement holds for bases with pK over 12. Is that right? Or is the word "measurable", earlier in the paragraph, the key, in that a pK outside these ranges is not measurable, precisely because any such acid or base is fully dissociated or fully de-protonated so there is nothing further to be measured? Mike Christie (talk) 01:01, 21 October 2008 (UTC)[reply]

-- Mike Christie (talk) 02:31, 20 October 2008 (UTC)[reply]

Those are very good points, but since I don't have much time now I'll just reply to one. "Oxonium" has been the IUPAC recommendation for decades, but it is one of their many recommendations that is not very widely adopted. One can find hundreds of books published in the last couple of years that prefer to use hydronium: 222 for hydronium, 127 for oxonium, and 16 for hydroxonium (but note that the number of oxonium is heavily overestimated because it can also mean the organic cation R3O+ and not only H3O+). It is my opinion that the author of the hydronium article was a bit overzealous. --Itub (talk) 06:46, 20 October 2008 (UTC)[reply]

The "Equilibrium constant" section has now been revised. I have re-instated the struck o notation as I believe that the IUPAC recommendation for the sign for standard is the plimsol line and this o is the nearest I could get to it. I am basing this on Quantities, Units and Symbols in Physical Chemistry, page 5. We are currently looking into this to see if the recommendation still stands. Petergans (talk) 16:55, 25 October 2008 (UTC)[reply]

More comments:

  • In the section "Acidity in nonaqueous solutions", it's stated that solvents can be "polar, protic, donor or non-polar". However from the table of dielectric constants below it appears that these are not mutually exclusive. To someone who doesn't know the topic it would seem more natural for the initial statement to say that solvents can be "polar or nonpolar, donor or not donor, and protic or aprotic". A separate point is that the table itself isn't consistent in the style it presents this data; you have "Non-polar, Donor", but "Polar donor" instead of "Polar, Donor". Is there a reason for the difference?
  • I'm also not clear what purpose this table serves. It does not present pK values, nor does any of the data in it appear to be used or even referenced afterwards in the article. You do refer to dielectric constants in that section but no calculation is given, so the numbers seem unnecessary.

I agree. The table was introduced by another editor (eaglefalconn) who, though a major stimulus to bringing the article to FAC status, has disappeared into thin air. I didn't want to offend him, but I did think that the table is superfluous. I will start to make corrections after I return to Leeds on Friday. Petergans (talk) 11:21, 21 October 2008 (UTC)[reply]

  • The sentence beginning "DMSO is widely used ..." is a run-on sentence.
  • The last two paragraphs of ""Acidity in nonaqueous solutions" refer first to oligomers forming by hydrogen bonding, and then to an apparently separate ("may also form") process called homoconjugation. The last sentence says that homoconjugation does not occur in aqueous solutions because the oligomers cannot form; this doesn't sound like an explanation, based on the earlier sentences, which made it appear that oligomers and homoconjugation are different, though both are dependent on hydrogen bonds.
  • In the section "Mixed solvents", why is "one" in italics in the phrase "defined as one"?
  • This probably isn't something you need to fix, but I will just mention that the link to the article on Gibbs free energy wasn't particularly helpful notationally; the notations used in the two articles are different enough that a minute's perusal didn't explain to me what your "R" was, for example. However, if you're using standard notation I don't think this is your problem. After some digging around in enthalpy and elsewhere, what I found in Van 't Hoff equation leads me to think that R is the gas constant and ΔHθ is the enthalpy change. If so I think it would be good to say so. Actually you use the enthalpy delta term earlier, so it could be defined there; you do refer to it as an enthalpy term here which I think suffices.
  • In the "Thermodynamics" section, I'm not clear what you mean by "critically selected".

I've reviewed everything but the last two subsections and should return to those tomorrow. -- Mike Christie (talk) 02:35, 21 October 2008 (UTC)[reply]

  • Again I'll reply to one of the easy questions. ;-) "Critically selected" means that these are the best available values for each substance in the expert opinion of the authors who compiled the table (R. Goldberg, N. Kishore, R. Lennen). (As opposed to an "uncritical" table, which might simply compile all the available data or use arbitrary selection criteria.) --Itub (talk) 08:17, 21 October 2008 (UTC)[reply]

More comments:

  • The illustrative link in the section on buffer solutions needs to be cut; see this guideline. If the picture is sufficiently valuable you could recreate it as an image in an Excel graph and then capture the result as a graphic file and upload it. You could also convert this to a footnote and link the diagram from the note.
  • In that same section, everything after the sentence mentioning MOPS seems not to be strictly relevant to the article topic. Can some or all of this be cut? If the intent is to point out the importance of buffer solutions, and hence indirectly of pK, then it might be better to shorten the list and add it to the end of the sentence that begins "Buffer solutions are used extensively ..." Also, do we need the MOPS example? Does it help the reader understand pKa?
  • "Ingestion of cyanide by mouth is potentially fatal, independently of pH, because of the reaction with cytochrome c oxidase." Why is this sentence included?

It is standard practice in chemistry to give hazard warnings in appropriate places. Is this not appropriate? I didn't want some adventurous schoolboy to think that it is safe to play with cyanide. Please advise. Petergans (talk) 11:44, 22 October 2008 (UTC)[reply]

That makes sense. Would it be appropriate to add a comment recommending this sort of interjection at Wikipedia:WikiProject_Chemicals/Style_guidelines#Safety? Mike Christie (talk) 11:56, 22 October 2008 (UTC)[reply]
  • The whole section on the importance of pKa values is too listy, and should be converted to prose. The way you're using the {{main}} template isn't standard; the intention is for {{main}} to indicate that you are summarizing because including the whole referenced article would make your article too long. (See summary style for the details.) Here you simply want to link to these articles because they cover the topic you are discussing. A straightforward link is all you need to accomplish this. I would suggest eliminating the bullets and their titles, and the main/further info links, and running the remaining text together in whatever order makes internal sense. The articles you are linking to should then be linked as part of your discussion; instead of headings they may now appear as introductory or linking sentences in the prose.

-- Mike Christie (talk) 01:44, 22 October 2008 (UTC)[reply]

We saw the bullet/list comment coming (See http://en.wikipedia.org/wiki/Talk:Acid_dissociation_constant#Another_round_of_editing) and I sandboxed various other ways of presenting the material. The problem with running the text together, which I tried, is that most of the applications are so disparate, the area of applications is so broad, that the resulting text will not make sense; in effect most of the applications only have pK in common. Would separate paragraphs be acceptable?

Regarding the use of the {{main}} template, this is an error of inex-Wiki-sperience. The point we were trying to make is that applications linked in that way are substantial topics in their own right. Petergans (talk) 11:44, 22 October 2008 (UTC)[reply]

  • Closing note: This article has a great start towards featured status, but with the amount of discussion already here, I think it will have a better chance at gaining Support if the issues raised are worked on outside of FAC, and a new FAC is presented in a few weeks. SandyGeorgia (Talk) 23:34, 25 October 2008 (UTC)[reply]
The above discussion is preserved as an archive. Please do not modify it. No further edits should be made to this page.
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