Bickelhaupt, F. M.Fernández López, Israel2024-10-182024-10-182024Bickelhaupt FM, Fernández I. What defines electrophilicity in carbonyl compounds. Chem Sci. 2024 Feb 6;15(11):3980-3987. doi: 10.1039/d3sc05595g. PMID: 38487236; PMCID: PMC10935700.10.1039/d3sc05595ghttps://hdl.handle.net/20.500.14352/109101The 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.engAttribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/journal articlehttp://dx.doi.org/10.1039/d3sc05595ghttps://pubs.rsc.org/en/content/articlelanding/2024/sc/d3sc05595gopen access547Química orgánica (Química)2306 Química Orgánica