The restricted rotation about the carbon–nitrogen bond of formanilide has been investigated by high-performance liquid chromatography. At lower temperatures, two peaks corresponding to two dynamic rotamers (E- and Z-form) have appeared on chromatograms, whereas at higher temperatures they have not been separated and a single peak has appeared on chromatograms, due to rapid bond rotation. The equilibrium concentration ratio of E- to Z-form has been found to vary in different solvents, suggesting the presence of solute–solvent and solute–solute interactions such as hydrogen bond formation. Determination of kinetic characteristics such as rate constant and activation energy of fast reactions has been established by high-performance liquid chromatography. The authors have named the present method “dynamic high-performance liquid chromatography,” in imitation of “dynamic nuclear magnetic resonance spectroscopy” which traces fast equilibrium.
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Moriyasu et al. (1984) studied this question.
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