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

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

Research output: Contribution to journalArticlepeer-review

30 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)417-422
Number of pages6
JournalTetrahedron
Volume61
Issue number2
DOIs
Publication statusPublished - 10 Jan 2005

Keywords

  • Carbonyl reactivity
  • DFT calculations
  • Electron-withdrawing effects
  • Electrophilicity

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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