Computational studies on chiral discrimination mechanism of phenylcarbamate derivatives of cellulose

The calculations of interaction energies between cellulose tris(phenylcarbamate) (CTPC) or cellulose tris(3,5-dimethylphenylcarbamate) (CDMPC) and trans-stilbene oxide (1) or benzoin (2) were performed by various methods. The purpose was to gain insight into the mechanism for the chiral recognition on phenylcarbamate derivatives of cellulose which are useful chiral stationary phases for HPLC. The calculations were roughly divided into two methods: 1) Enantiomers were generated around the NH proton and the C=O oxygen of the carbamoyl group of CTPC and CDMPC which are considered to be the most important adsorption sites, and then the interaction energy was calculated. 2) Enantiomers were randomly generated by the Monte Carlo method on the surface of CTPC and CDMPC, and then the interaction energy was calculated. The results of both calculations were in good agreement with the results in the chromatographic resolution of 1 and 2 by CTPC and CDMPC.