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Molecular complexes of sulfonamides. Part 1. 1∶1 complexes between sulfadimidine [4-amino-N-(4,6-dimethyl-2-pyrimidinyl)benzenesulfonamide] and 2- and 4-aminobenzoic acids

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Abstract

The crystal and molecular structures of the 1∶1 complexes sulfadimidine·2-aminobenzoic acid (I) and sulfadimidine·4-aminobenzoic acid (II) are described and compared with known structures containing sulfadimidine. In each complex, molecular association is maintained by one N-H⋯O hydrogen bond, and one O-H⋯N hydrogen bond involving the imino N and one pyrimidinyl N atom of sulfadimidine and the two carboxyl O atoms of the aromatic acid. The conformation of the sulfadimidine molecule inII is unusual for anN 1-substituted arylsulfonamide. Molecular dimensions for the complexed aminobenzoic acids are virtually the same as those reported for the free acids. Partial correlation between carboxylic acid strengths and the hydrogen bonded N⋯O distances is observed in sulfadimidine complexes of this type.

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  1. Department of Chemistry, University of Cape Town, Private Bag, 7700, Rondebosch, South Africa

    Mino R. Caira

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  1. Mino R. Caira
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Caira, M.R. Molecular complexes of sulfonamides. Part 1. 1∶1 complexes between sulfadimidine [4-amino-N-(4,6-dimethyl-2-pyrimidinyl)benzenesulfonamide] and 2- and 4-aminobenzoic acids. Journal of Crystallographic and Spectroscopic Research 21, 641–648 (1991). https://doi.org/10.1007/BF01161088

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  • DOI: https://doi.org/10.1007/BF01161088

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