Abstract
Ab initio molecular orbital calculations using the 321G basis set provide good approximations of the experimental geometries of substituted strained organic molecules. A series of disubstituted prismanes have been calculated at this level and the effects of substituents upon geometries rationalized in terms of the molecular orbitals of the parent molecule. The results are compared with four experimental structures. Evidence is presented which indicates that prismane conjugates more strongly with π-accepting substituents than does cyclopropane, consistent with earlier predictions. Brief comparison is made with the quadricyclane (homoprismane) series. © 1988.