Kinetic Studies of Fast Equilibrium by Means of High-performance Liquid Chromatography. XII. Rate Constants and Energy Barriers of Intramolecular Carbonyl–Nitrogen Bond Rotation of o-Substituted Acetanilides

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Abstract
A novel high-performance liquid chromatographic(HPLC) method has been proposed to determine the rate constants and activation energies of the interconversion between two labile species existing in equilibrium in solution. The rotational energy barriers to intramolecular bond rotation about the carbonyl–nitrogen bonds of several o-substituted acetanilides have been determined by this method. These energy barriers have been found to increase when bulkier groups are attached at the o-position on the benzene ring. These have also been determined by a dynamic nuclear magnetic resonance spectroscopic(DNMR) method, which gives good agreement with the HPLC results.

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