Talk:2-Pyridone

2-Pyridone favored in water

" Nonpolar solvents favour the 2-Pyridone whereas in polar solvents like alcohols and water the 2-Hydroxypyridone is favoured. "

I believe this is backwards, plus the spelling error in 2-Hydroxypyridone, so I'm changing it. It's 2-hydroxypyridine in gas phase, and the more polar the solvent, the more stable the 2-pyridone. The explanation for this is stabilization of charge separation in high dielectric environments. 2-pyridone has greater charge separation, as can be seen by considering its mesionic aromatic resonance contributor. There's a discussion of the solvent effects and a large table of pKts for substituted 2-pyridones in J Elguero, C Marzin, AR Katritzky, P Linda, The Tautomerism of Heterocycles, Advances in Heterocyclic Chemistry, Supplement 1 (1976).

High boiling point?

The boiling point of 300+ degrees centrigrade is much higher than reported elsewhere in (internet) publications. But most refer to the hydroxypyridine tautomer, so I'm not sure. Could anyone confirm? Wim van Dorst 20:56, 30 January 2006 (UTC).

There are several boiling points mentioned in literature. I will give literature link when I will have next possibility to use Beilstein-Crossfire!Stone 07:13, 31 January 2006 (UTC)

Me culpa mea macima culpa! The boiling point is cited in literature but in reality decomposition takes place at 280°C which is cited in other literature.Stone 19:13, 11 February 2006 (UTC)

High pKa? or low pKa?

In Kirk-Othmer (4th) under Pyridines, I see that the pKa for 2-pyridone is 1.25. That's quite some difference from the 11+ as currently listed in the table. Or is this a mix up of various tautomers? Wim van Dorst 21:11, 30 January 2006 (UTC).

Bordwell lists 2-pyridone as 17.0 in DMSO. However, in water it has two pKas: 0.75 and 11.62. ~K 04:29, 31 January 2006 (UTC)

The 0.75 pKa would be for a protonated pyridone, while the 11.62 pKa is for a neutral pyridone. 5/8/2012 — Preceding unsigned comment added by 128.32.207.175 (talk) 16:40, 8 May 2012 (UTC)

New literature

Transition States for Glucopyranose Interconversion Brett E. Lewis, Nankishoresing Choytun, Vern L. Schramm, and Andrew J. Bennet J. Am. Chem. Soc.; 2006; 128(15) pp 5049 - 5058; (Article) DOI: 10.1021/ja0573054 ADALSTEINSSON H, BRUICE TC JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 120 (14): 3440-3447 APR 15 1998

NMR data?

What is the reference for the NMR data of this compound? I have taken an NMR of this compound and it does not at all match what is presented. —Preceding unsigned comment added by 169.229.198.168 (talk) 20:51, 21 May 2010 (UTC)

My apologies, this data is in MeOD, mine was in CDCl3. However, it might be nice to have the exact reference for the NMR data in that section anyway? —Preceding unsigned comment added by 169.229.198.168 (talk) 20:53, 21 May 2010 (UTC)

Sorry for the NMR data of 2-Pyridone it comes from several sources

• doi:10.1021/j100842a001
• [1]
• doi:10.1002/bbpc.19620660211
• doi:10.1021/jo00823a029

--Stone (talk) 22:15, 21 May 2010 (UTC)

Should we even have such a standalone section for analytical data? I think we should remove the section, and provide only images if there are features to discuss. WP:NOTMANUAL? --Rifleman 82 (talk) 02:02, 22 May 2010 (UTC)

This is not a manual! This is analytical data, For example the Acetone article has a Acetone (data page) where this kind of information would fit. But the article is not long enough and has not enough data to create a extra page. If I finde time I will improve the article. I had enough of 2-Pyridone after my phd,so I abandoned the page for some time.--Stone (talk) 07:46, 22 May 2010 (UTC)

Haha, alright. --Rifleman 82 (talk) 10:04, 22 May 2010 (UTC)

Dead link

During several automated bot runs the following external link was found to be unavailable. Please check if the link is in fact down and fix or remove it in that case!

• http://www.znaturforsch.com/sb/s59b1121.pdf
  • In 2-Pyridone on 2011-05-25 06:55:53, 401 Authorization Required
  • In 2-Pyridone on 2011-06-10 04:44:19, 401 Authorization Required

--JeffGBot (talk) 04:44, 10 June 2011 (UTC)

Dead link 2

During several automated bot runs the following external link was found to be unavailable. Please check if the link is in fact down and fix or remove it in that case!

• http://jeq.scijournals.org/cgi/content/abstract/14/4/580
  • In 2-Pyridone on 2011-05-25 06:55:51, Socket Error: 'getaddrinfo failed'
  • In 2-Pyridone on 2011-06-10 04:44:28, Socket Error: 'getaddrinfo failed'

--JeffGBot (talk) 04:44, 10 June 2011 (UTC)

Requested move

The following discussion is an archived discussion of a requested move. Please do not modify it. Subsequent comments should be made in a new section on the talk page. Editors desiring to contest the closing decision should consider a move review. No further edits should be made to this section.

The result of the move request was: not moved (withdrawn). -- Ed (Edgar181) 11:57, 30 May 2013 (UTC)

---

2-Pyridone → 2-pyridone – Please put your reason for moving here. Tony (talk) 09:25, 26 May 2013 (UTC)

Per WP:MOSCAPS ("Wikipedia avoids unnecessary capitalization") and WP:TITLE. A significant part of the literature (including NIH-related articles) uses lower case, which will also match the formatting of related article titles. Tony (talk) 09:25, 26 May 2013 (UTC)

Asked the question on the Chemistry project. It might be helpful to wait for the discussion there. --Stone (talk) 16:49, 26 May 2013 (UTC)

• Oppose. The initial letter of a term is normally capitalized in article titles, as if the title were the beginning of a sentence, and here the initial letter is the P. (Note this doesn’t mean we should capitalize the name in the middle of a sentence.) I’m not familiar with the academic literature, though: if it can be shown that titles, captions, and sentences beginning with this name (or others like it) usually use lower case for the first letter, I would go along with that (despite my personal preference—and, AFAICT, IUPAC usage). Non-initial occurrences shouldn’t count, because the fact that in “I added the acid to the water“ the nouns begin with lower-case letters doesn’t imply the A & W should be lower-case in the article titles of Acid and Water.—Odysseus1479 18:14, 26 May 2013 (UTC)

P.S. Please see MOSCHEM/NAME.–Odysseus1479 20:28, 26 May 2013 (UTC)

Then I'm wondering why 2-pyridone, downcased, is scattered through the article text. And "2-hydroxypyridine". Tony (talk) 01:36, 27 May 2013 (UTC) Ah, just saw Odysseus's comment. On one level not very intuitive, but I understand now. Tony (talk) 01:37, 27 May 2013 (UTC)

Note that wherever such names begin a sentence in the article, they’re capitalized. (Unless my quick scan missed something.) The principle is that certain prefixes descriptive of structure, in particular the numerals that indicate points of attachment, are not treated as part of the name, but as if they were symbols. Some have a fixed, conventional typographic presentation as well, regardless of environment, like e.g. the copyright symbol. So where a chemical name needs to be capitalized, as at the beginning of a title or a sentence, this occurs at the first letter of the name proper.—Odysseus1479 02:44, 27 May 2013 (UTC)

Then I withdraw the request. Tony (talk) 03:02, 27 May 2013 (UTC)

The above discussion is preserved as an archive of a requested move. Please do not modify it. Subsequent comments should be made in a new section on this talk page or in a move review. No further edits should be made to this section.

External links modified (January 2018)

Hello fellow Wikipedians,

I have just modified 2 external links on 2-Pyridone. Please take a moment to review my edit. If you have any questions, or need the bot to ignore the links, or the page altogether, please visit this simple FaQ for additional information. I made the following changes:

• Added archive https://archive.is/20080830100452/http://jeq.scijournals.org/cgi/content/abstract/14/4/580 to http://jeq.scijournals.org/cgi/content/abstract/14/4/580
• Added archive https://web.archive.org/web/20100527212347/http://www.mesg.anl.gov/Ed_web_files/oloughlinPDF_Files/CREC1989.pdf to http://www.mesg.anl.gov/Ed_web_files/oloughlinPDF_Files/CREC1989.pdf

When you have finished reviewing my changes, you may follow the instructions on the template below to fix any issues with the URLs.

This message was posted before February 2018. After February 2018, "External links modified" talk page sections are no longer generated or monitored by InternetArchiveBot. No special action is required regarding these talk page notices, other than regular verification using the archive tool instructions below. Editors have permission to delete these "External links modified" talk page sections if they want to de-clutter talk pages, but see the RfC before doing mass systematic removals. This message is updated dynamically through the template {{source check}} (last update: 5 June 2024).

• If you have discovered URLs which were erroneously considered dead by the bot, you can report them with this tool.
• If you found an error with any archives or the URLs themselves, you can fix them with this tool.

Cheers.—InternetArchiveBot (Report bug) 03:08, 24 January 2018 (UTC)