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-beta-naphthol and their analogues by molecular mechanics methods. The results showed that the driving force of chiral recognition came from the pi-pi 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 similar to 3, and preferred to bind with R-enantiomers of bi-beta-naphthol and its analogues 4 similar to 6. This was consistent with the HPLC experimental results. The separation factors were 1.02, 1.04 and 1.11 respectively for compounds 1 similar to 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
