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The hydrogen-bonding networks of 2-amino-4-phenyl-1,3-thiazole derivatives

The hydrogen-bonding networks of 2-amino-4-phenyl-1,3-thiazole derivatives
The hydrogen-bonding networks of 2-amino-4-phenyl-1,3-thiazole derivatives
The solid-state packing arrays of nine 4-phenyl substituted 2-amino-1,3-thiazoles have been examined and their hydrogen-bonding networks discussed. The nine compounds, in addition to 2-amino-1,3-thiazole 1, were 2-amino-4-phenyl-1,3-thiazole 2, 2-amino-4-phenyl-1,3-thiazolium bromide monohydrate 3, ethyl 2-amino-4-phenyl-1,3-thiazole-5-carboxylate 4, 2-amino-4-(3-coumarin)-1,3-thiazole 5, 2-amino-4-(4-methylphenyl)-1,3-thiazole 6, 2-amino-4(2-hydroxyphenyl)-1,3-thiazole 7, 2-amino-4-(4-bisphenyl)-1,3-thiazole 8, 2-amino-4-(1-naphthyl)-1,3-thiazole 9, and 2-amino-4-(2-naphthyl)-1,3-thiazolium bromide 10. The single-crystal x-ray structures of 1-5 have been previously reported while the structures of 6-10 are presented in this paper. A variety of different packing motifs are observed with only four (4, 5, 6 and 9) exhibiting the characteristic R-2(2)(8) hydrogen-bonded 2-amino-1,3-thiazole dimers. In two of these four structures (6 and 9) potential N-H...? hydrogen-bonding interactions exist whereas all remaining structures exhibit a combination of N-H...N with either N-H...O, N-H...S or N-H...Br associations in their hydrogen-bonding networks.
2-amino-1, 3-thiazole, hydrogen bond, x-ray crystal structure
123-136
Lynch, Daniel E.
edff6860-7481-48b9-ac5a-25a7fd23efdd
McClenaghan, Ian
85f27d63-60d4-4d37-96db-1c8fe67d4fcc
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Lynch, Daniel E.
edff6860-7481-48b9-ac5a-25a7fd23efdd
McClenaghan, Ian
85f27d63-60d4-4d37-96db-1c8fe67d4fcc
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8

Lynch, Daniel E., McClenaghan, Ian, Light, Mark E. and Coles, Simon J. (2002) The hydrogen-bonding networks of 2-amino-4-phenyl-1,3-thiazole derivatives. Crystal Engineering, 5 (2), 123-136. (doi:10.1016/S1463-0184(02)00011-4).

Record type: Article

Abstract

The solid-state packing arrays of nine 4-phenyl substituted 2-amino-1,3-thiazoles have been examined and their hydrogen-bonding networks discussed. The nine compounds, in addition to 2-amino-1,3-thiazole 1, were 2-amino-4-phenyl-1,3-thiazole 2, 2-amino-4-phenyl-1,3-thiazolium bromide monohydrate 3, ethyl 2-amino-4-phenyl-1,3-thiazole-5-carboxylate 4, 2-amino-4-(3-coumarin)-1,3-thiazole 5, 2-amino-4-(4-methylphenyl)-1,3-thiazole 6, 2-amino-4(2-hydroxyphenyl)-1,3-thiazole 7, 2-amino-4-(4-bisphenyl)-1,3-thiazole 8, 2-amino-4-(1-naphthyl)-1,3-thiazole 9, and 2-amino-4-(2-naphthyl)-1,3-thiazolium bromide 10. The single-crystal x-ray structures of 1-5 have been previously reported while the structures of 6-10 are presented in this paper. A variety of different packing motifs are observed with only four (4, 5, 6 and 9) exhibiting the characteristic R-2(2)(8) hydrogen-bonded 2-amino-1,3-thiazole dimers. In two of these four structures (6 and 9) potential N-H...? hydrogen-bonding interactions exist whereas all remaining structures exhibit a combination of N-H...N with either N-H...O, N-H...S or N-H...Br associations in their hydrogen-bonding networks.

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More information

Published date: 2002
Keywords: 2-amino-1, 3-thiazole, hydrogen bond, x-ray crystal structure

Identifiers

Local EPrints ID: 19814
URI: http://eprints.soton.ac.uk/id/eprint/19814
PURE UUID: 3f5d1af6-dd3b-4d67-916c-95b875de8415
ORCID for Mark E. Light: ORCID iD orcid.org/0000-0002-0585-0843
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

Catalogue record

Date deposited: 21 Feb 2006
Last modified: 08 Jan 2022 02:50

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Contributors

Author: Daniel E. Lynch
Author: Ian McClenaghan
Author: Mark E. Light ORCID iD
Author: Simon J. Coles ORCID iD

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