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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

✍ Scribed by Jens Wolff, J. ;Gredel, Frank ;Hillenbrand, Daniela ;Irngartinger, Hermann

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
832 KB
Volume
1996
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

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.

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