What defines electrophilicity in carbonyl compounds
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Updated: Jun 30, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
F Matthias Bickelhaupt1,2,3, Israel Fernández4
1Department of Chemistry and Pharmaceutical Sciences, AIMMS, Vrije Universiteit Amsterdam The Netherlands f.m.bickelhaupt@vu.nl.
Abstract:
The origin of the electrophilicity of a series of cyclohexanones and benzaldehydes is investigated using the activation strain model and quantitative Kohn-Sham molecular orbital (MO) theory. We find that this electrophilicity is mainly determined by the electrostatic attractions between the carbonyl compound and the nucleophile (cyanide) along the entire reaction coordinate. Donor-acceptor frontier molecular orbital interactions, on which the current rationale behind electrophilicity trends is based, appear to have little or no significant influence on the reactivity of these carbonyl compounds.
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