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Shape and size effects in the crystal structures of complexes of 1,3,5-trinitrobenzene with some trigonal donors: the benzene–thiophene exchange rule

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Title Shape and size effects in the crystal structures of complexes of 1,3,5-trinitrobenzene with some trigonal donors: the benzene–thiophene exchange rule
 
Creator THALLAPALLY, PRAVEEN K
CHAKRABORTY, KAKALI
CARRELL, HL
KOTHA, SAMBASIVARAO
DESIRAJU, GAUTAM R
 
Subject crystal engineering
crystal chemistry
protocols
crystallographic
 
Description The crystal chemistry of molecular complexes of several trigonal donor molecules with the trigonal acceptor 1,3,5-trinitrobenzene, TNB, is reported. Generally, replacement of a moiety by another of similar shape and size does not change the overall packing. The 1:1:1 (triphenylisocyanurate)·(TNB)·(benzene) solvate is isostructural to the corresponding 1:1:1 thiophene solvate, confirming the so-called benzene–thiophene exchange rule. The 1:1 complex of tris-2,4,6-(4-methylphenyl)-1,3,5-triazine and TNB is layered and the layers have quasi-trigonal symmetry. The triazine ring may be replaced by a phenyl ring without any change in the crystal structure. Thus, 1,3,5-tris(4-methylphenyl)benzene and TNB form an isostructural 1:1 complex. Such shape/size exchange may be further explored in the 1:1 complex of 1,3,5-tris[5-(2-chlorothienyl)]benzene and TNB. Here both phenyl–thienyl and chloro–methyl exchanges are simultaneously possible and yet another isostructural complex is obtained. Finally, the 1:1 complex of 1,3,5-tris(2-thienyl)benzene and TNB is also found to have a very similar structure. However, when 1,3,5-triphenylbenzene and TNB are taken in 1:1 ratio in solution, the result is a 1:3 molecular complex. This is unexpected in view of the phenyl–thienyl exchange rule, and some rationalisation is provided for the unusual formation of this 1:3 complex. Many of these structures are pertinent from the viewpoint of carry-over of trigonal molecular symmetry into the crystal, a contemporary theme in the engineering of crystal structures for octupolar non-linear optical applications, while ready access to the 1,3,5-trisubstituted benzenes for this study was made possible by a general and efficient protocol for the synthesis of these compounds from the corresponding acetyl aromatics.
 
Publisher Elsevier
 
Date 2009-03-05T12:38:22Z
2011-11-25T18:38:10Z
2011-12-26T13:06:56Z
2011-12-27T05:54:54Z
2009-03-05T12:38:22Z
2011-11-25T18:38:10Z
2011-12-26T13:06:56Z
2011-12-27T05:54:54Z
2000
 
Type Article
 
Identifier Tetrahedron 56(36), 6721-6728
0040-4020
http://dx.doi.org/10.1016/S0040-4020(00)00493-2
http://hdl.handle.net/10054/879
http://dspace.library.iitb.ac.in/xmlui/handle/10054/879
 
Language en