The conformation of levopimaric acid investigated by high-level ab initio MO calculations. Possibility of the CH/π hydrogen bond

Abstract

Ab initio MO calculations were carried out, at the MP2/6-311G(d,p) level of approximation, to investigate the conformation of levopimaric acid. It has been found that the folded conformation is more stable than the extended conformation. The result is consistent with the documented experimental data. The reason for the relative stability of the folded conformation has been sought in the context of the CH/π hydrogen bond. Short non-bond distances have been disclosed between CHs in the 10β angular methyl group and sp 2 carbons of the conjugated diene ring in the more stable folded conformers of model compounds. We suggest that the folded conformation of levopimaric acid is a consequence of an attractive molecular force, the CH/π hydrogen bond.