Theoretical study of the hydrophobic character of the dimerization of dexanabinol

An extensive theoretical study of the dimers of dexanabinol and related compounds has been performed at the ab initio Hartree-Fock (HF)/6-31G** and B3LYP/6-31G** levels. Theoretical calculations indicate that the most stable conformer of dexanabinol does not have intramolecular hydrogen bonds. The most stable dimer of dexanabinol forms intermolecular hydrogen bonds in which the phenol groups act as hydrogen bond donors and the allylic OH groups as acceptors is energetically more favored. The dimer results agree with previous PM3 results. In addition, the interaction of dexanabinol with two water molecules was studied. The effects of solvation were calculated with the Onsager model with full geometry optimization. The solvation results indicate that the most stable dimer of dexanabinol is affected little by solvation. (C) 2003 Wiley Periodicals, Inc.