Theoretical study on chiral recognition mechanism of ethyl-3-hydroxybutyrate with permethylated β-cyclodextrin

► The inclusion interactions between PMβCD and enantiomers of (R/S)-EHB were simulated using PM3 and ONIOM methods. ► The binding geometries of the most stable (R/S)-EHB/PMβCD complexes obtained by ONIOM method are fully different. ► The (R)-EHB/PMβCD complex is more stable than (S)-EHB/PMβCD. ► The main driving forces are weak hydrogen bonding, dipole-dipole interaction, hydrophobic interaction, among others.