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MP2 study of the gas phase elimination mechanism of some neutral amino acids and their ethyl esters
Author(s) -
Pérez Johan R.,
Loroño Marcos,
Domínguez Rosa M.,
Córdova Tania,
Chuchani Gabriel
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.1364
Subject(s) - chemistry , decarboxylation , amino acid , gas phase , carboxylic acid , picolinic acid , ethyl ester , ethylene , medicinal chemistry , stereochemistry , organic chemistry , catalysis , biochemistry
The mechanisms of the gas phase elimination of N , N ‐dimethylglycine, picolinic acid, and N ‐phenylglycine and their ethyl esters have been examined at Möller–Plesset MP2/6‐31G (d, p) level of theory. The ethyl esters of these 2‐amino carboxylic acids produce the corresponding amino carboxylic acid and ethylene in a rate‐determining step. However, the unstable intermediate amino carboxylic acid rapidly decarboxylate to give the corresponding amino compound. These calculations imply a concerted, semi‐polar six‐membered cyclic transition state type of mechanism for the ethyl esters, and a non‐synchronous five‐membered cyclic transition state for the amino acids decarboxylation. The present results support previous mechanistic consideration of the elimination of the above‐mentioned compounds in the gas phase. Copyright © 2008 John Wiley & Sons, Ltd.