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Updated: May 18, 2026

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Eight isostructural 4,4'-disubstituted N-phenylbenzenesulfonamides
Thomas Gelbrich1, Terence L Threlfall, Michael B Hursthouse
1Institute of Pharmacy, University of Innsbruck, Austria. thomas.gelbrich@uibk.ac.at
Abstract:
The isostructural crystals of 4-cyano-N-(4-methoxyphenyl)benzenesulfonamide, C(14)H(12)N(2)O(3)S, (I), N-(4-methoxyphenyl)-4-(trifluoromethyl)benzenesulfonamide, C(14)H(12)F(3)NO(3)S, (II), 4-iodo-N-(4-methoxyphenyl)benzenesulfonamide, C(13)H(12)INO(3)S, (III), 4-bromo-N-(4-methoxyphenyl)benzenesulfonamide, C(13)H(12)BrNO(3)S, (IV), 4-chloro-N-(4-methoxyphenyl)benzenesulfonamide, C(13)H(12)ClNO(3)S, (V), 4-fluoro-N-(4-methoxyphenyl)benzenesulfonamide, C(13)H(12)FNO(3)S, (VI), N-(4-chlorophenyl)-4-methoxybenzenesulfonamide, C(13)H(12)ClNO(3)S, (VII), and 4-cyano-N-phenylbenzenesulfonamide, C(13)H(10)N(2)O(2)S, (VIII), contain infinite chains composed of N-H···O(sulfonyl) hydrogen-bonded molecules. The crystal structures of (I)-(VIII) have been compared using the XPac software and quantitative descriptors of isostructurality were generated [Gelbrich, Threlfall & Hursthouse (2012). CrystEngComm, 14, 5454-5464]. Certain isostructural relationships in this series involve molecules with substantially different spatial demands, e.g. (VI) and (VIII) are related by the simultaneous interchange of F→CN on the benzenesulfonamide ring and OMe→H on the N-phenyl ring, which indicates that the geometry of the three-dimensional crystal-packing mode of (I)-(VIII) is unusually adaptable to different molecular shapes.
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