Origin of the synchronicity on the transition structures of polar Diels-Alder reactions. Are these reactions [4 + 2] processes?

Luis R. Domingo, M. José Aurell, Patricia Pérez, Renato Contreras

Resultado de la investigación: Contribución a una revistaArtículo

116 Citas (Scopus)

Resumen

The transition structures (TSs) for a series of related Diels-Alder reactions between cyclopentadiene and mono-, di-, tri-, and tetracyanoethylene derivatives have been studied with use of DFT methods at the B3LYP/6-31G* computational level. The increase of the electron-withdrawing substitution on ethylene increases the rate of these polar cycloadditions. However, the symmetric arrangement of cis and trans 1,2-di- and tetracyanoethylenes decreases the effectiveness of the substitution, which can be related to the symmetry found at the corresponding TSs. A DFT analysis of the global and local electrophilicity power of these series of cyano ethylenes provides a sound explanation about the nature of these synchronous processes. The present theoretical study is in agreement with the experimental outcomes.

Idioma originalInglés
Páginas (desde-hasta)3884-3890
Número de páginas7
PublicaciónJournal of Organic Chemistry
Volumen68
N.º10
EstadoPublicada - 16 may 2003

Áreas temáticas de ASJC Scopus

  • Química orgánica

Huella Profundice en los temas de investigación de 'Origin of the synchronicity on the transition structures of polar Diels-Alder reactions. Are these reactions [4 + 2] processes?'. En conjunto forman una huella única.

  • Citar esto