A theoretical and experimental study on mechanism of N-(4-hydroxycyclohexyl)-acetamide cis-trans epimerization

The mechanism of N-(4-hydroxycyclohexyl)-acetamide cis-trans epimerization was studied by means of the density functional theory (DFT) method. A new possible reaction pathway is proposed. The calculations further indicate that the proposed pathway is preferable. In addition, quantum mechanical calculations were employed to study temperature, pressure, and the solvent effect on the proposed mechanism which could be used to predict the ratio of two anomers expected from the proposed pathway. Furthermore, the experimental results are in good accordance with the computation outcomes.