Amylose-tris(3,5-dimethylphenylcarbamate) (ADMPC) and aminopropylated silica gel(APS) were prepared after the reported methods. ADMPC was immobilized on APS from tetrahydrofuran solution with a coating amount of 15%. The chiral stationary phase was packed in a stainless-steel column(150 mm x 4.6 mm i.d.) by slurry method. The column was used for the enantioseparation of 6 glycerin monosulfides and 4 glycerin bisulfides. Mixtures of hexane and 2-propanol were used as mobile phases. The enantiomers of the monosulfides could be separated quite well, while those of the bisulfides could not at all. This phenomenon shows that the ether oxygen atom of the monosulfides plays a key role in the chiral discrimination process. The retention time of the solutes increases significantly as the amount of 2-propanol decreases. This shows the main interaction between the solutes and the chiral stationary phase is hydrogen bonding. A dynamic model is presented to account for the chiral discrimination mechanism.