Stereochemistry of arylamides - 2. AM1 SCF and SCRF quantum-chemical modelling of some N-(1-naphthyl) amides

The results of AM1 self-consistent field (SCF) and self-consistent reaction field (SCRF) quantum-chemical calculations of the conformational equilibria and dynamics at the amide group of a series of N-(1-naphthyl)amides are reported. In accordance with the experimental observation, the presence of two conformers, corresponding to the E- and Z-form of the amide, has been predicted by the calculations. The AM1 multi-cavity self-consistent reaction field calculation results predict the change in the relative population of these two conformers due to the change in the dielectric medium. The isobutyryl and benzoyl amides are predicted to have one conformer (the E-form) strongly predominant in solutions.