Three salts from the reactions of cysteamine and cystamine withL-(+)-tartaric acid

Abstract

Reaction between cysteamine (systematic name: 2-aminoethanethiol, C2H7NS) and L-(+)-tartaric acid [systematic name: (2R,3R)-2,3-dihydroxybutanedioic acid, C4H6O6] results in a mixture of cysteamine tartrate(1−) monohydrate, C2H8NS+·C4H5O6−·H2O, (I), and cystamine bis[tartrate(1−)] dihydrate, C4H14N2S22+·2C4H5O6−·2H2O, (III). Cystamine [systematic name: 2,2′-dithiobis(ethylamine), C4H12N2S2], reacts with L-(+)-tartaric acid to produce a mixture of cystamine tartrate(2−), C4H14N2S22+·C4H4O62−, (II), and (III). In each crystal structure, the anions are linked by O—H...O hydrogen bonds that run parallel to theaaxis. In addition, hydrogen bonding involving protonated amino groups in all three salts, and water molecules in (I) and (III), leads to extensive three-dimensional hydrogen-bonding networks. All three salts crystallize in the orthorhombic space groupP212121.