Testing the Validity of the Conventional Resonance Model for Protonated Carbonyl, Imine and Thiocarbonyl Compounds. An Ab Initio Valence Bond Study

Braïda, Benoît, Bundhoo, Dilshaad ORCID: 0000-0003-0262-9868, Engels, Bernd and Hiberty, Philippe C. (2008) Testing the Validity of the Conventional Resonance Model for Protonated Carbonyl, Imine and Thiocarbonyl Compounds. An Ab Initio Valence Bond Study. Organic Letters, 10 (10). pp. 1951-1954. doi:10.1021/ol800391d

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Abstract

The conventional resonance model describes protonated carbonyls, imines, and thiocarbonyls by a superposition of two structures, one pi polar-covalent and the other of carbenium type. The validity of this model is clearly supported by high level valence bond calculations, giving a 32% weight for the carbenium form in protonated carbonyl, 19% in protonated formamine and thioformaldehyde. The carbenium form is further stabilized by pi-donating substituents. Solvation effects do not fundamentally change the gas-phase picture.

Item Type:	Article
Subjects:	G Geography. Anthropology. Recreation > G Geography (General)
Divisions:	Schools and Research Institutes > Countryside and Community Research Institute
Depositing User:	Anne Pengelly
Date Deposited:	28 Mar 2014 08:25
Last Modified:	01 Aug 2021 21:27
URI:	https://eprints.glos.ac.uk/id/eprint/317

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