Imamura A, Koda M, Kato S
Gan. 1979 Jun;70(3):291-6.
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.
采用CNDO/2方法并结合能量最小化方法计算了萘、蒽、菲和苯并[a]芘二醇环氧化物的电子结构。通过这些方法，自动获得了分子的最稳定几何结构。通过比较菲二醇环氧化物和蒽二醇环氧化物的总能量，结合化学反应性研究了湾区的作用。得出结论，当二醇环氧化物通过SN1机制与生物系统的成分反应时，湾区起着重要作用。此外，由于存在湾区以及分子尺寸较大，苯并[a]芘二醇环氧化物显示出非常高的反应活性。当反应通过SN2机制进行时，发现湾区对分子的化学反应性影响很小。
