Effect of electron-withdrawing substituents on the electrophilicity of carbonyl carbons
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Date
2005-01
Profesor/a GuÃa
Facultad/escuela
Idioma
en
Journal Title
Journal ISSN
Volume Title
Publisher
Elsevier
Nombre de Curso
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item.page.dc.rights
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.
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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