Flat versus twisted rotamers of 2,4-­disubstituted thiazoles: the effect of intermolecular hydrogen bonds

In the title compounds, 2‐amino‐4‐(2‐chloro‐4,5‐di­methoxy­phenyl)‐1,3‐thia­zole, C11H11ClN2O2S, (I), and 4‐(2‐chloro‐4,5‐di­methoxy­phenyl)‐2‐methyl‐1,3‐thia­zole, C12H12ClNO2S, (II), the dihedral angles between the thia­zole moiety and the chloro­aryl group are 51.61 (10) and 8.44 (14)°, respectiv...

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Bibliographic Details
Published in:Acta crystallographica. Section C, Crystal structure communications Crystal structure communications, 2002-03, Vol.58 (3), p.o151-o153
Main Authors: Bernès, Sylvain, Berros, Martha I., Rodríguez de Barbarín, Cecilia, Sánchez-Viesca, Francisco
Format: Article
Language:English
Subjects:
Condensed matter: structure, mechanical and thermal properties
Exact sciences and technology
Heterocyclic compounds
Organic compounds
Physics
Structure of solids and liquids
crystallography
Structure of specific crystalline solids
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Summary:In the title compounds, 2‐amino‐4‐(2‐chloro‐4,5‐di­methoxy­phenyl)‐1,3‐thia­zole, C11H11ClN2O2S, (I), and 4‐(2‐chloro‐4,5‐di­methoxy­phenyl)‐2‐methyl‐1,3‐thia­zole, C12H12ClNO2S, (II), the dihedral angles between the thia­zole moiety and the chloro­aryl group are 51.61 (10) and 8.44 (14)°, respectively. This difference is a consequence of intermolecular hydrogen bonds forcing the stabilization of a twisted rotamer in (I). Substitution of the amino function by a methyl group precludes these contacts, giving a flat rotamer in (II).
ISSN:0108-2701
1600-5759
DOI:10.1107/S0108270102000598