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Effect of electron-withdrawing substituents on the electrophilicity of carbonyl carbons |
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| Authors: | R. Contreras,J. André s |
| Affiliation: | a Departamento de Química, Facultad de Ciencias, Universidad de Chile, Casilla 653, Santiago, Chile b Departament de Cienciès Experimentals, Universitat Jaume I, Box 224, 12080 Castelló, Spain c Instituto de Ciencia Molecular, Departamento de Química Orgánica, Universidad de Valencia, Dr. Moliner 50, 46100 Burjassot, Valencia, Spain d Departamento de Ciencias Químicas, Facultad de Ecología y Recursos Naturales, Universidad Andrés Bello, República 275, Santiago, Chile |
| Abstract: | 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. |
| Keywords: | Carbonyl reactivity Electron-withdrawing effects Electrophilicity DFT calculations |
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