Ab initio study on the molecular structure of trans-1,2-dihydroxy-1,2-dihydro-8-fluoronaphthalene.

F A Beland, W B Melchior, V J Klimkowski, L Schäfer

Index: Cancer Lett. 33(2) , 205-13, (1986)

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Abstract

The molecular geometries of two conformations (diequatorial and diaxial) of trans-1,2-dihydroxy-1,2-dihydro-8-fluoronaphthalene have been refined the ab initio gradient method at the 4-21G level to determine the effect of fluoro substitution on the conformational and structural properties of naphthalene dihydrodiols. As with trans-1,2-dihydroxy-1,2-dihydronaphthalene, the conformation with diequatorial hydroxyl groups is the most stable. The structural differences for the fluorinated and unfluorinated naphthalene dihydrodiols are discussed and the possible consequences of the structural and conformational trends on the metabolism of dihydrodiols to dihydrodiol epoxides are considered.