ArticleChemical science2024
What defines electrophilicity in carbonyl compounds.
Article in Chemical science, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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6 citing papers in PubMed.
- Akamptisomerism Beyond Porphyrins: Bond Angle Reflection and Stereochemical Divergences in Corrole- and Porphyrin-Anchored B-O-B Bridges.Inorganic chemistry · 2026Article
- Efficient Synthesis of Chemically Recyclable Polyamides via Substituent Effects-Enabled Mechanistic Pathway.Angewandte Chemie (International ed. in English) · 2025Article
- Heteroaromatic swapping in aromatic ketones.Nature communications · 2025Article
- Understanding Small Molecule Activation Promoted by Heavier Benzene 1,4-diides: Interplay Between Diradical Character and Aromaticity.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Hydroxymethanesulfonate formation accelerated at the air-water interface by synergistic enthalpy-entropy effects.Nature communications · 2025Article
- Origin of the Felkin-Anh(-Eisenstein) model: a quantitative rationalization of a seminal concept.Chemical science · 2024Article
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Authors and funding
2 authors.
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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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