Collect. Czech. Chem. Commun. 1988, 53, 2986-2994

MNDO study of the E-Z isomerization mechanism of H2C=NR molecules (R = H, CH3, NH2, OH, F)

Peter Ertl

Department of Chemistry, Comenius University, 842 15 Bratislava


The geometry and E-Z isomerization mechanism were studied by the MNDO method for H2C=NR molecules with R = H, CH3, NH2, OH and F. All the molecules save H2C=NNH2 possess a plane of symmetry and isomerize by the inversion mechanism, whereas H2C=NNH2 has a nonsymmetrical geometry and the inversion-rotation mechanism is more favourable for its isomerization. Dependent considerably on the substituent at the nitrogen atom, the isomerization barrier height increases in order R = CH3, H, NH2, OH, F.