MP2 study of the gas phase elimination mechanism of some neutral amino acids and their ethyl esters

Johan R. Pérez, Marcos Antonio Loroño Gonzalez, Rosa M. Domínguez, Tania Córdova, Gabriel Chuchani

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5 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)402-408
Number of pages7
JournalJournal of Physical Organic Chemistry
Volume21
Issue number5
DOIs
StatePublished - May 2008
Externally publishedYes

Bibliographical note

Copyright:
Copyright 2008 Elsevier B.V., All rights reserved.

Keywords

  • Gas phase elimination
  • Kinetics
  • Mechanism
  • MP2/6-31G (d, p) calculations
  • N,N-dimethylglycine
  • N-phenylglycine and their ethyl esters
  • Picolinic acid

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