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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
Author(s) -
Jens Wolff J.,
Gredel Frank,
Hillenbrand Daniela,
Irngartinger Hermann
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619960717
Subject(s) - chemistry , planarity testing , intramolecular force , steric effects , tris , hydrogen bond , acceptor , ring (chemistry) , electronic effect , crystallography , computational chemistry , photochemistry , stereochemistry , molecule , organic chemistry , biochemistry , physics , condensed matter physics
The 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.