Structures and Properties of Tris(donor)‐Tris(acceptor)‐Substituted Benzenes, 8!!. On the Balance of Steric, Electronic and Hydrogen Bond Effects in 1,3,5‐Tris(amino)‐2,4,6‐Tris(acceptor)‐Substituted Benzenes

AbstractThe conformational properties of triamino‐substituted 1,3,5‐trinitrobenzenes were studied by X‐ray crystallography, dynamic NMR spectroscopy, and semiempirical calculations. As amino substituents all possible combinations of a dialkyl‐, a monoalkylamino, and an amino group were used. All derivatives have radialene‐like structures with the central six‐membered ring distorted from planarity. The geometric form of the latter was linked with the electronic organization of the π system. Despite the presence of up to six intramolecular hydrogen bonds, semi‐empirical calculations reproduce experimental geometries quite well.