Semi-maleate salts ofL- andDL-serinium: the first example of chiral and racemic serinium salts with the same composition and stoichiometry

Abstract

L-Serinium semi-maleate, (I), and DL-serinium semi-maleate, (II), both C3H8NO3+·C4H3O4−, provide the first example of chiral and racemic anhydrous serine salts with the same organic anion. A comparison of their crystal structures with each other, with the structures of the pure components (L-serine polymorphs, DL-serine and maleic acid) and with other amino acid maleates is important for understanding the formation of the crystal structures, their response to variations in temperature and pressure, and structure–property relationships. As in other known crystal structures of amino acid maleates, there are no direct links between the semi-maleate anions in the two new structures. The serinium cations have different conformations in (I) and (II). In (I), they are linked into infinite chainsviahydrogen bonds between carboxylic acid and hydroxy groups. In (II), there are no such chains formed by the serinium cations. In both (I) and (II), there areC22(12) chains consisting of alternating semi-maleate anions and serinium cations. Two types of such chains are present in (I) and (II), termedC22(12) andC22(12)′. In (I), these chains, lying in the same plane, are further linked to each otherviahydrogen bonds, whereas in (II) they are not.