Issue 11, 2024

What defines electrophilicity in carbonyl compounds

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.

Graphical abstract: What defines electrophilicity in carbonyl compounds

Supplementary files

Article information

Article type
Edge Article
Submitted
20 Oct 2023
Accepted
05 Feb 2024
First published
06 Feb 2024
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2024,15, 3980-3987

What defines electrophilicity in carbonyl compounds

F. M. Bickelhaupt and I. Fernández, Chem. Sci., 2024, 15, 3980 DOI: 10.1039/D3SC05595G

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