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Organic & Biomolecular Chemistry Vol - 4 Issue - 4

Organic & Biomolecular Chemistry Vol - 4 Issue - 3

Organic & Biomolecular Chemistry Vol -3

Organic & Biomolecular Chemistry Vol -2

A DFT study of the structures of pyruvic acid isomers and their decarboxylation

Content Provider	Royal Society of Chemistry (RSC)
Author	Kakkar, Rita Radhika, N. P. Pathak, Mallika
Copyright Year	2006
Abstract	Pyruvic acid and its isomers, including the enol tautomers and enantiomeric lactone structures, have been investigated at the B3LYP/6-311 + + G(3df,3pd) level, and it is found that a keto form with trans CmethylCketoCacidOhydroxyl and cis CketoCacidOH, and with one methyl hydrogen in a synperiplanar position with respect to the keto oxygen, is the most stable. This agrees with previous theoretical and experimental determinations. However, no minimum corresponding to protonated pyruvate could be located, although previous semiempirical calculations had found such structures. Decarboxylation by different possible routes was then studied. It was found that the direct formation of acetaldehyde, the most stable of the resulting C2H4O isomers, via a four-center-like transition state is the most feasible, although there is a high activation barrier of 70 kcal mol−1. In contrast to semiempirical calculations, it is found that no hydroxyethylidene–carbon dioxide complex exists as a product, and no transition state leading to the dissociation to hydroxethylidene could be located.
Starting Page	886
Ending Page	895
Page Count	10
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	4
Issue Number	5
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/b516355b
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Carboxylic acid Decarboxylation Enol Alkane stereochemistry Lactone Pyruvic acid Dissociative Hydrogen bond Nucleophile Acetaldehyde
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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