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).
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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