Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science

1 : 1 Molecular Complexes of 4-Amino-N-(4,6-dimethylpyrimidin-2-yl)benzene-sulfonamide (Sulfamethazine) with Indole-2-carboxylic Acid and 2,4-Dinitrobenzoic Acid

Daniel E. Lynch, Pardeep Sandhu and Simon Parsons

Australian Journal of Chemistry 53(5) 383 - 387
Published: 2000


The 1 : 1 molecular adducts of 4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide (Sulfamethazine) with respectively indole-2-carboxylic acid (1) and 2,4-dinitrobenzoic acid (2) have been prepared and their X-ray crystal structures determined. The acid groups in both structures form associative R22 (8) graph set hydrogen-bonding interactions across the N(11)–H/N(17) site of Sulfamethazine. Acomparison of the two distances between relevant non-hydrogen atoms in this configuration reveals that this association is not symmetrical. An average difference of 0.144 Å is observed for seven listed complexes of Sulfamethazine, five having been previously reported. This average difference compares with a value of 0.265 Å for the same interaction seen in carboxylic acid adducts of 2-aminopyrimidine.

Keywords: Sulfamethazine; carboxylic acid adducts; X-ray crystal structure.

© CSIRO 2000

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