NDLI: Differing Patterns in the Self-Assembly of Radially Anchored Imidazoles, 1,3,5-Tris(1H-imidazol-2-yl)benzene and 1,3-Bis(1H-imidazol-2-yl)benzene

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Differing Patterns in the Self-Assembly of Radially Anchored Imidazoles, 1,3,5-Tris(1H-imidazol-2-yl)benzene and 1,3-Bis(1H-imidazol-2-yl)benzene

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Journal of Chemical Crystallography : Volume 37

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Differing Patterns in the Self-Assembly of Radially Anchored Imidazoles, 1,3,5-Tris(1H-imidazol-2-yl)benzene and 1,3-Bis(1H-imidazol-2-yl)benzene

Content Provider	Springer Nature Link
Author	Rajesh, Y. B. R. D. Ranganathan, Subramania Gilardi, Richard D. Karle, Isabella L.
Copyright Year	2007
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. 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 A. Infinite stacks of the TFA salt from 1,3,5-tris(1H-imidazol-2-yl)benzene with a separation of 3.57 Å between atoms in separate planes (The TFA moiety has been omitted for clarity).B. Tetrameric assembly of 1,3-bis(1H-imidazol-2-yl)benzene, mediated by water molecules. 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 Y.B.R.D. Rajesh, $^{(2)}$ Subramania Ranganathan, $^{(2)}$* Richard D. Gilardi $^{(1,3)}$ and Isabella L. Karle, $^{(1)}$*(1) Laboratory for the Structure of Matter, Naval Research Laboratory, Washington, D.C. 20375-5341(2) Discovery Laboratory, Organic III, Indian Institute of Chemical Technology, Hyderabad 500 007, India(3) Retired
Starting Page	39
Ending Page	48
Page Count	10
File Format	PDF
ISSN	10741542
Journal	Journal of Chemical Crystallography
Volume Number	38
Issue Number	1
e-ISSN	15728854
Language	English
Publisher	Springer US
Publisher Date	2007-11-03
Publisher Place	Boston
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Infinite parallel stacks of novel 1,3,5-tris imidazole Unusual tetrameric assembly of 1,3-bis imidazole Assembly mediated by water Inorganic Chemistry Physical Chemistry Crystallography Organometallic Chemistry
Content Type	Text
Resource Type	Article
Subject	Chemistry Condensed Matter Physics

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