Structural and Kinetic Investigations on Nitrogen Inversion of Some Aziridine Compounds Using Density Functional Theory Study

Abstract

Using density function theory methods (B3LYP) the molecular structures of various substituted aziridine compounds, both in their ground states as well as their planar shaped transition states, corresponding to nitrogen inversion process, were determined. The energy, enthalpy, free energy changes along with the activation energy and rate constants for such nitrogen inversions were determined for these substituted aziridine compounds. The impacts of introduction of substituents like methyl, ethyl, isopropyl, phenyl on nitrogen inversion were determined. The change of barrier energy for nitrogen inversion on changing the substituent on N-atom of the aziridine ring was also determined. The results predict that introduction of electronegative element on N-atom of the aziridine moiety leads to an increase in energy barrier; the out of ring substituent also increases the barrier energy towards such inversion. Thus such increase in barrier energy will facilitate the isolation of various chiral aziridine units.