Differing patterns in the self-assembly of radially anchored imidazoles, 1,3,5-Tris(1 H -imidazol-2-yl)benzene and 1,3-Bis(1 H -imidazol-2-yl)benzene

Rajesh, Y. B. R. D. ; Ranganathan, Subramania ; Gilardi, Richard D. ; Karle, Isabella L. (2008) Differing patterns in the self-assembly of radially anchored imidazoles, 1,3,5-Tris(1 H -imidazol-2-yl)benzene and 1,3-Bis(1 H -imidazol-2-yl)benzene Journal of Chemical Crystallography, 38 (1). pp. 39-48. ISSN 1074-1542

Full text not available from this repository.

Official URL: http://www.springerlink.com/content/445052756v81k6...

Related URL: http://dx.doi.org/10.1007/s10870-007-9286-6

Abstract

The novel 3-fold symmetric 1,3,5-tris(1H-imidazol-2-yl)benzene, having a propensity for a 3-fold salt formation by hydrogen bonding at the periphery, was prepared from oxidation of the hexahydro imidazole precursor. The transformation proved difficult and, of the many reagents tried, only barium manganate and o-iodoxy benzoic acid were successful. The oxidation to the aromatic 1,3,5-tris imidazolyl benzene produces dramatic changes, particularly when the X-ray structures of their tris-TFA (trifluoroacetic acid) salts are compared. While the hexahydro precursor exhibited a herringbone type arrangement in the crystal, the oxidation resulted in almost co-planar molecules that formed parallel stacks separated by 3.57 Å between the atoms in separate planes. 1,3-Bis(1H-imidazole-2-yl)benzene is an attractive core unit for assembly using a variety of auxiliaries. Several attempts to complex the bis-imidazole with organic acids failed. These efforts lead to the serendipitous discovery of a novel tetrameric assembly, mediated by water molecules, which was confirmed by crystallization of the bis imidazole from water.

Item Type:Article
Source:Copyright of this article belongs to Springer.
Keywords:Infinite Parallel Stacks of Novel 1, 3, 5-tris Imidazole; Unusual Tetrameric Assembly of 1, 3-bis Imidazole; Assembly Mediated by Water
ID Code:70683
Deposited On:21 Nov 2011 04:33
Last Modified:21 Nov 2011 04:33

Repository Staff Only: item control page