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

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

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