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

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.

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Indexación: Scopus

Keywords

Chemical Reactivity, Electronegativity, Parr, carbonyl derivative, carbonyl, phenylacetic acid derivative, carbon nuclear magnetic resonance, DFT calculations, Electron-withdrawing effects, Electrophilicity

Citation

Tetrahedron, Volume 61, Issue 2, Pages 417 - 42210 January 2005

DOI

DOI: 10.1016/j.tet.2004.10.085

URI

http://repositorio.unab.cl/xmlui/handle/ria/19123

Collections

Fac.CV - Artículos de Revista

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