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The N-inversion energies and nucleophilic ring-opening reactions of N-substituted aziridine compounds are investigated using B3LYP/6-31+ methods, where substituents (R) on the nitrogen atom has been H (1), Me (2), Ph (3), Bn (4), CHMePh (5), (6), COPh (7) and (8). The N-inversion energy with X group are decreased as the following order: R = CHMePh (17.06 kcal/mol) Me (16.97) Bn (16.70) H (16.64) (12.18) Ph (8.91) COPh (5.75) (5.48). For reactivity of the ring opening toward cyanide ion, the aziridine 6 (R=) is shown to be the most reactive one. During the ring opening of aziridine 6 by CN, the torsional OCNC angle becomes near to , where the geometry allows for the effective incorporation of electrons of the nitrogen atom to the C=O bond. It would be a possible driving force for nucleophilic ring opening reaction as well as decreasing the N-inversion energy barrier. Regarding to the regioselectivity, the orientation of nucleophile in ring opening reaction appears to be different in the case of 9 and 10. The results are discussed in terms of steric/electronic effect of the -substituents.

Substituents Effect on Aziridine Chemistry: N-Inversion Energy, Reactivity and Regioselectivity of Nucleophilic Ring-opening