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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.

SUBMITTER: Bickelhaupt FM

PROVIDER: S-EPMC10935700 | biostudies-literature | 2024 Mar

REPOSITORIES: biostudies-literature

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What defines electrophilicity in carbonyl compounds.

Bickelhaupt F Matthias FM Fernández Israel I

Chemical science 20240206 11

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 b ...[more]

PMID: 38487236

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