High-performance liquid chromatography(HPLC) of six phenyl methylcarbamates at low column temperatures on normal phase chromatography using hydroxyl-group chemically-bonded silica gel packing achieved the separation of rotamers. The population ratios of rotamers were determined for different conditions such as solvent composition and concentration. The rotational-energy barriers to intramolecularbond rotation about the carbonyl–nitrogen bonds were determined for four p-substituted phenyl methylcarbamates, and it was found that the energy barriers were higher when electron-withdrawing groups were substituted.
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Moriyasu et al. (1986) studied this question.
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