Ab initio study on the molecular structure of the naphthalene metabolite, trans-1,2-dihydroxy-1,2-dihydronaphthalene.

The molecular geometries of three conformations of trans-1,2-dihydroxy-1,2-dihydronaphthalene have been refined by an ab initio gradient procedure at the 4-21G level to determine the effect of dihydrodiol conformation on arene structure. The preferred conformation is an equatorial form similar to the most stable conformation of ethylene glycol. All the structures investigated have similar arene geometries. The effect of the various conformations on metabolism of dihydrodiols to dihydrodiol epoxides is considered.