The simplified model of (R)-phenylglycine based chiral stationary phase (Chirex 3001) was built to investigate the process of chiral recognition of benzoin and bi-β-naphthol and their analogues by molecular mechanics methods. The results showed that the driving force of chiral recognition came from the π-π stacking, hydrogen bond and van der Waals interactions between the host and the guest molecule. The host preferred to bind with S-enantiomers of benzoin and its analogues 1～3, and preferred to bind with R-enantiomers of bi-β-naphthol and its analogues 4～6. This was consistent with the HPLC experimental results. The separation factors were 1.02, 1.04 and 1.11 respectively for compounds 1～3 when n-hexane/ 1,2-dichloroethane/ethanol (V∶V∶V＝83.5∶15∶1.5) was used as mobile phase, and the R-enantiomers were eluted first. The separation factors were 1.23, 1.26 and 1.11 respectively when n-hexane/
chloroform/ethanol (V∶V∶V＝78.5∶20∶1.5) was used as mobile phase, and the S-enantiomers were eluted first.

Key words: chiral recognition, molecular mechanics, chiral resolution, benzoin, bi-β-naphthol