| 2-hydroxypyridine <--> 2-pyridone tautomerization: catalytic influence of formic acid. | |
| | |
MedLine Citation:
|
PMID: 16854025 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
|
A 1:1 hydrogen-bonded complex between 2-pyridone and formic acid has been characterized using laser-induced-fluorescence excitation and dispersed fluorescence spectroscopy in a supersonic jet expansion. Under the same expansion condition, the fluorescence signal of the tautomeric form of the complex (2-hydroxypyridine...formic acid) is absent, although both the bare tautomeric molecules exhibit well-resolved laser-induced-fluorescence spectra. Quantum chemistry calculation at the DFT/B3LYP/6-311++G** level predicts that in the ground electronic state the activation barrier for tautomerization from hydroxy to keto form in bare molecules is very large (approximately 34 kcal/mol). However, the process turns out to be nearly barrierless when assisted by formic acid, and double proton transfer occurs via a concerted mechanism. |
| | |
Authors:
|
Montu K Hazra; Tapas Chakraborty |
Related Documents
:
|
16270575 - Comparison of the acid combinations in microwave-assisted digestion of marine sediments... 17943205 - Efficient resolution of racemic n-benzyl beta3-amino acids by iterative liquid-liquid e... 8490195 - Antitumor activity of a new series of platinum complexes: trans(+/-)-1,2-cyclohexanedia... 7085185 - Comparative study of 99mtc labeled hepatobiliary agents based on naphthalene and simila... 6517895 - Effects of essential fatty acids on prostaglandin biosynthesis. 2329565 - Retinobenzoic acids. 5. retinoidal activities of compounds having a trimethylsilyl or t... |
Publication Detail:
|
Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
|
Title: The journal of physical chemistry. A Volume: 110 ISSN: 1089-5639 ISO Abbreviation: J Phys Chem A Publication Date: 2006 Jul |
Date Detail:
|
Created Date: 2006-07-20 Completed Date: 2007-08-14 Revised Date: - |
Medline Journal Info:
|
Nlm Unique ID: 9890903 Medline TA: J Phys Chem A Country: United States |
Other Details:
|
Languages: eng Pagination: 9130-6 Citation Subset: IM |
Affiliation:
|
Department of Chemistry, Indian Institute of Technology, Kanpur, UP 208016, India. |
Export Citation:
|
APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
|
Catalysis Electrons Formic Acids / chemistry* Isomerism Models, Molecular Molecular Conformation Pyridones / chemistry* Spectrometry, Fluorescence |
| Chemical | |
Reg. No./Substance:
|
0/Formic Acids; 0/Pyridones; 142-08-5/2-hydroxypyridine; 64-18-6/formic acid |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
Previous Document: Direct determination of absolute configuration of methyl-substituted phenyloxiranes: combined experi...
Next Document: Revealing successive steps of deprotonation of L- phosphoserine through 13C and 31P chemical shieldi...