Abstract
The dipole moments of acetanilide and a series of five p-substituted benzoylacetanilides, 1a — e, were determined in benzene at 30 °C. The method of comparing the observed dipole moment of a compound with those calculated for its various hypothetical structures was employed to deduce firstly the most probable configuration of acetanilide and subsequently, those of the keto and enol tautomers of the aroylacetanilides.The equilibrium constants, KT 's, derived from dipole moments results were satisfactorily correlated by the Hammet substituent constants, σ+ 's, the equation being log KT = 0.724 σ+ — 0.132, with r = 0.996 and s = ± 0.032.
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