MNDO/H and AM1 studies of nitro enamines with intramolecular hydrogen bonds

Abstract

A set of nitro enamines with intramolecular hydrogen bonding have been studied by the MNDO/H and the AM1 method. Geometries, isomer populations, and rotational barriers around the carbon–carbon double bond predicted by the calculations are compared with experimental results. Solvent effects on isomeric equilibria are considered. It is shown that semiempirical calculations supply a reasonable description of the static and dynamic properties of these systems, although accurate predictions are possible only by including solvent effects.