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A structural study of tautomerism and hydrogen-bonding in supramolecular assemblies

A structural study of tautomerism and hydrogen-bonding in supramolecular assemblies
A structural study of tautomerism and hydrogen-bonding in supramolecular assemblies
The synthesis and X-ray structures of four new crystalline materials incorporating 'dimers' assembled from two different units possessing complementary hydrogen bonding motifs are reported; namely, phthalimide and 3-iminoisoindolinone or 2-guanidinobenzimidazole (or selected methylated derivatives) and 2-guanidinobenzoxazole. The bonding within each dimer involves a triplet of hydrogen bonds. The extended supramolecular structures are compared with each other as well as with two related structures described previously. The effect of using complementary DAD/ADA motifs that are not symmetrical on the respective supramolecular structures is also examined as is the prospect of incorporating different tautomeric components into the supramolecular structures. The presence of a very short, proton-transferred hydrogen bond within the respective triplets is also discussed.
crystal engineering, self-assembly, supramolecular, hydrogen bonding x-ray-diffraction, metal-complexes, bis(2-guanidinobenzimidazolo)nickel(ii), 2-guanidinobenzimidazole, arrays
1061-0278
567-578
Bishop, Michael M.
e3acabeb-12cd-4b15-b643-c5cdb0a15270
Coles, Simon J.
65bb28e4-4917-43f5-a770-a00017d6783f
Lee, Andrew H.W.
b6a4af6b-0686-44d9-968a-779ba5cbf613
Lindoy, Leonard F.
217831c1-05b8-4c7a-b4a6-848d2b21eedd
Parkin, Andrew
4646aceb-2a78-41c5-a2cd-394746b869e0
Thorn-Seshold, Oliver T.
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Turner, Peter
af5f357d-f9f5-42fc-a739-761653b4cb87
Bishop, Michael M.
e3acabeb-12cd-4b15-b643-c5cdb0a15270
Coles, Simon J.
65bb28e4-4917-43f5-a770-a00017d6783f
Lee, Andrew H.W.
b6a4af6b-0686-44d9-968a-779ba5cbf613
Lindoy, Leonard F.
217831c1-05b8-4c7a-b4a6-848d2b21eedd
Parkin, Andrew
4646aceb-2a78-41c5-a2cd-394746b869e0
Thorn-Seshold, Oliver T.
b070485c-f421-4304-937d-85cddd0d7a0e
Turner, Peter
af5f357d-f9f5-42fc-a739-761653b4cb87

Bishop, Michael M., Coles, Simon J., Lee, Andrew H.W., Lindoy, Leonard F., Parkin, Andrew, Thorn-Seshold, Oliver T. and Turner, Peter (2005) A structural study of tautomerism and hydrogen-bonding in supramolecular assemblies. Supramolecular Chemistry, 17 (7), 567-578. (doi:10.1080/10610270500333927).

Record type: Article

Abstract

The synthesis and X-ray structures of four new crystalline materials incorporating 'dimers' assembled from two different units possessing complementary hydrogen bonding motifs are reported; namely, phthalimide and 3-iminoisoindolinone or 2-guanidinobenzimidazole (or selected methylated derivatives) and 2-guanidinobenzoxazole. The bonding within each dimer involves a triplet of hydrogen bonds. The extended supramolecular structures are compared with each other as well as with two related structures described previously. The effect of using complementary DAD/ADA motifs that are not symmetrical on the respective supramolecular structures is also examined as is the prospect of incorporating different tautomeric components into the supramolecular structures. The presence of a very short, proton-transferred hydrogen bond within the respective triplets is also discussed.

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More information

Published date: 2005
Keywords: crystal engineering, self-assembly, supramolecular, hydrogen bonding x-ray-diffraction, metal-complexes, bis(2-guanidinobenzimidazolo)nickel(ii), 2-guanidinobenzimidazole, arrays

Identifiers

Local EPrints ID: 44388
URI: https://eprints.soton.ac.uk/id/eprint/44388
ISSN: 1061-0278
PURE UUID: 989bd2b6-6246-49f6-a3f0-00e87b7a7d9b

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Date deposited: 01 Mar 2007
Last modified: 13 Mar 2019 21:07

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Contributors

Author: Michael M. Bishop
Author: Simon J. Coles
Author: Andrew H.W. Lee
Author: Leonard F. Lindoy
Author: Andrew Parkin
Author: Oliver T. Thorn-Seshold
Author: Peter Turner

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