Theoretical study of the formation of the β-CD-N-tosyl-2-phenyl-aziridine adduct

Quantum chemical methods have been employed to study the formation of the adduct of N-tosyl-2-phenyl-aziridine encaged in β-CD. The results show that,when N-tosyl-2-phenyl-aziridine enters into the cavity of β-CD,step by step phenyl orientation leads to the system becoming more stable,and the dipole interaction between N-tosyl-2-phenyl-aziridine and β-CD plays an important role. Analysis of electron density by topological studies indicated that hydrogen bonds are formed between the host and guest molecules when the phenyl group of the guest molecules points to the secondary rim of β-CD. As a result,it is suggested that the orientation effects on N-tosyl-2-phenyl-aziridine in the cavity of β-CD might mostly be attributed to interactions between the host and guest molecules,such as hydrogen bonding and dipole-dipole interactions.