K. Baldridge, J. Siegel
Nov 1, 1993
Citations
0
Influential Citations
33
Citations
Journal
Journal of the American Chemical Society
Abstract
The structures of 1,3,5-triamino-2,4,6-trinitrobenzene (2) and related compounds (3-5) are studied using ab initio Hartree-Fock (6-31G(D)) and local density functional (LDF) computational methods. In contradiction to published structures for 2 predicted from semiempirical data, both ab initio methods predict a planar structure in accord with the experimental X-ray crystallographic study. It is concluded that appreciable «push-pull» conjugation is present in 2 and that the interaction between flanking groups is mainly attractive through cyclic hydrogen bonding. Computations on 3-5 were used to gauge the affinity for some rings to distort into boat instead of chair forms. The relative electron density distributions for 2 and 5 are discussed