Effect of electron-withdrawing substituents on the electrophilicity of carbonyl carbons

R. Contreras, J. Andrés, L. R. Domingo, R. Castillo, P. Pérez

Resultado de la investigación: Contribución a una revistaArtículo

27 Citas (Scopus)

Resumen

The substituent effects on the carbonyl carbon atom for a series of twelve substituted phenyl acetates have been rationalized using a global electrophilicity index. This index is linearly correlated with the experimental reaction rate coefficients. We found that, in contrast to the proposed interpretation based on experimental 13C NMR chemical shifts and ground state destabilization calculations, the electrophilicity of carbonyl compounds increases due to the effect promoted by electron-withdrawing groups in these systems.

Idioma originalInglés
Páginas (desde-hasta)417-422
Número de páginas6
PublicaciónTetrahedron
Volumen61
N.º2
DOI
EstadoPublicada - 10 ene 2005

Áreas temáticas de ASJC Scopus

  • Bioquímica
  • Descubrimiento de medicamentos
  • Química orgánica

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