Premium
Effect of aqueous solvation on the structures of pyruvic acid isomers and their reactions in solution: a computational study
Author(s) -
Kakkar Rita,
Pathak Mallika,
Gahlot Pragya
Publication year - 2008
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1270
Subject(s) - chemistry , tautomer , solvation , aqueous solution , protonation , pyruvic acid , decarboxylation , computational chemistry , reaction mechanism , molecule , catalysis , aqueous two phase system , organic chemistry , ion
The pyruvic acid molecule and its various isomers have been studied in aqueous solution in order to understand the mechanism of decarboxylation. The tautomeric equilibrium remains in favor of the keto form in aqueous solution, but the energy difference between the two tautomers decreases. The anion also exists in the keto form in aqueous solution. Good agreement between the calculated and observed gas phase protonation and basicity values is obtained, and the calculated p K a value is also in reasonable agreement with the literature value. The importance of the catalytic mechanism may be gauged from the fact that, in the absence of an enzymatic pathway, the reaction has high activation barrier and may not occur at all. Copyright © 2007 John Wiley & Sons, Ltd.