ELECTRONIC INTERACTIONS IN PHENYL ACETATES AND ACETANILIDES

Abstract

“The relative importance of an inductive vs. a resonance mechanism for the high carbonyl absorption frequency of phenyl acetate and acetanilide has been investigated. A study of the C-O frequency shifts in their meta and para-subtituted derivatives clearly shows that the inductive mechanism is responsible for the frequency shift in phenyl acetate, but a resonance mechanism is more appropriate in the acetanilides. This is supported by a study of their respective Stuart-Briegleb molecular models which, on the basis of steric inhibition of resonance due to lack of coplanarity within the molecule, indicates that a resonance mechanism is relatively unimportant in phenyl acetate.”