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Molecular orbital study on the metabolic pathway through the diol epoxide form of carcinogenic benzene in comparison
1Department of Chemistry, Faculty of Science, Hiroshima University, Japan.
Abstract:
The stabilization energy for the hydronium-ion-catalyzed hydrolysis of benzene diol epoxide (BDE) in the configuration of anti- or syn-form has been estimated by using the semi-empirical molecular orbital calculations with the CNDO/2 method. The values for the formation of carbonium ion from BDE are compared with those from benzo[a]pyrene, and it is suggested that the anti-form BDE belongs to a relatively strong reactive group with benzo[a]pyrene and benz[a]anthracene. The reactivity of BDE to the cation is completely different from that of polycyclic aromatic hydrocarbon diol epoxides (PAHDEs) from the viewpoint of the electronic structure; the cation from the anti-form BDE has a three center-four electron bond, whereas cations from PAHDEs do not have such a bond and the aromaticity still remains.
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