COMPUTATIONAL ANALYSIS OF THE STRUCTURES, BOND PROPERTIES, AND ELECTROSTATIC POTENTIALS OF SOME NITROTETRAHEDRANES AND NITROAZATETRAHEDRANES
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The structures and properties of six nitro derivatives of tetrahedrane and its mono and diaza analogues have been determined by means of ab initio self-consistent field computations. Geometries optimized at the 3-21G level were used to calculate bond deviation indices (as measures of bond strain), bond orders (to determine relative bond strengths), and molecular electrostatic potentials, as guides to reactive behavior. The bond properties (length, degree of strain, and strength) are significantly influenced by the conformation of the nitro group, although there was found to be essentially no energy barrier to its rotation. For the polynitro derivatives, the general result is a slight strengthening of C-C bonds. The molecular electrostatic potentials are also considerably affected by the electron-withdrawing -NO2 substituents; the negative potentials associated with the strained C-C bonds in unsubstituted systems are absent, and the basicities of the aza nitrogens are greatly reduced. 1989 American Chemical Society.
