Abstract
The conformational preferences of phenylmorphan have been determined by the MM2 (Molecular Mechanics II) program using full energy minimization. Chair-chair conformations of the cyclohexane and piperidine rings were preferred by 2.6 kcal/mol or more. With the preferred chair-chair conformation, three stable orientations of the phenyl ring were found with relative energies of 0.0, 1.0, and 1.2 kcal/mol. The barrier to rotation of the phenyl ring was computed to be 4 kcal/mol. The preferred phenyl orientation for the (+)-antipode was similar to that of morphine using a previously postulated molecular model for opiate substrates. This is consistent with the typical morphine-like pharmacological properties of this antipode. The preferred phenyl orientation of the atypical (-)-antipode appears to be most similar to the phenyl orientation that is invariably preferred by more active prodine antipodes. The preferred conformer was similar to the one observed by X-ray crystallography.
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