Theoretical study of the gas-phase decomposition of neutral α-amino acid ethyl esters. Part 1 - The elimination of N,N-dimethylglycine ethyl ester and ethyl 1-piperidineacetate

Jairo Quijano, Rafael Notario, Eduardo Chamorro, Luis A. León, Claudia Sánchez, Gustavo Alarcón, J. Camilo Quijano, Gabriel Chuchani

Resultado de la investigación: Contribución a una revistaArtículorevisión exhaustiva

16 Citas (Scopus)

Resumen

Theoretical studies of the thermolysis of two α-amino acid ethyl esters in the gas phase were carried out using ab initio theoretical methods, at the HF/6-31G(d) and the MP2/6-311 + G(2d,p)//MP2/6-31G(d) levels of theory. The reactions studied have two steps: the first one corresponds to the formation of ethylene and a neutral amino acid intermediate via a six-membered cyclic transition state, and the second is the rapid decarboxylation of this intermediate via a five-membered cyclic transition state. The progress of the first step of the reactions was followed by means of the Wiberg bond indices. The results indicate that the transition states have an intermediate character between reactants and products, and the calculated synchronicities show that the reactions are concerted and slightly asynchronous. The bond-breaking processes are more advanced than the bond-forming processes, indicating a bond deficiency in the transition states. The kinetic parameters calculated for both reactions agree very well with the available experimental results.

Idioma originalInglés
Páginas (desde-hasta)413-419
Número de páginas7
PublicaciónJournal of Physical Organic Chemistry
Volumen15
N.º7
DOI
EstadoPublicada - jul 2002

Áreas temáticas de ASJC Scopus

  • Química física y teórica
  • Química orgánica

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