title: A molecular orbital study on the chemical reactivity and biological activity of polycyclic aromatic hydrocarbon diol-epoxides in connection with bay region theory.
abstract: Electronic structures of naphthalene-, anthracene-, phenanthrene-, and benzo-[a]pyrene-diol-epoxides were calculated by using CNDO/2 method together with the energy minimization method. By using these methods, the most stable geometry of molecules was automatically obtained. By comparing the total energy of phenanthrene-diol-epoxide with that of anthracene-diol-epoxide, the role of the bay region was studied in connection with the chemical reactivity. It is concluded that the bay region plays an important role when the diol-epoxide reacts with the component of the biological system via SNl mechanism. Moreover, benzo[a]pyrene-diol-epoxide was shown to be very reactive because fo the presence of the bay region as well as the large size of the molecule. When reaction proceeds via SN2 mechanism, the bay region is found to have little effect on the chemical reactivity of the molecules.
mesh_terms: D000873:Anthracenes; D001580:Benzopyrenes; D055598:Chemical Phenomena; D002621:Chemistry; D002627:Chemistry, Physical; D004852:Epoxy Compounds; D008968:Molecular Conformation; D009281:Naphthalenes; D010616:Phenanthrenes; D011083:Polycyclic Compounds; D013329:Structure-Activity Relationship
chemical_list: D000873:Anthracenes; D001580:Benzopyrenes; D004852:Epoxy Compounds; D009281:Naphthalenes; D010616:Phenanthrenes; D011083:Polycyclic Compounds