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: Article

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

Huella dactilar

Carbonyl compounds
Chemical shift
Ground state
Reaction rates
Carbon
Nuclear magnetic resonance
Electrons
Atoms
phenyl acetate
Carbon-13 Magnetic Resonance Spectroscopy

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Citar esto

Contreras, R. ; Andrés, J. ; Domingo, L. R. ; Castillo, R. ; Pérez, P. / Effect of electron-withdrawing substituents on the electrophilicity of carbonyl carbons. En: Tetrahedron. 2005 ; Vol. 61, N.º 2. pp. 417-422.
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Effect of electron-withdrawing substituents on the electrophilicity of carbonyl carbons. / Contreras, R.; Andrés, J.; Domingo, L. R.; Castillo, R.; Pérez, P.

En: Tetrahedron, Vol. 61, N.º 2, 10.01.2005, p. 417-422.

Resultado de la investigación: Article

TY - JOUR

T1 - Effect of electron-withdrawing substituents on the electrophilicity of carbonyl carbons

AU - Contreras, R.

AU - Andrés, J.

AU - Domingo, L. R.

AU - Castillo, R.

AU - Pérez, P.

PY - 2005/1/10

Y1 - 2005/1/10

N2 - 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.

AB - 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.

KW - Carbonyl reactivity

KW - DFT calculations

KW - Electron-withdrawing effects

KW - Electrophilicity

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U2 - 10.1016/j.tet.2004.10.085

DO - 10.1016/j.tet.2004.10.085

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SP - 417

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JO - Tetrahedron

JF - Tetrahedron

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