A. Jayaraman, V. Balasubramaniam, S. Valiyaveettil
Oct 19, 2004
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Journal
Crystal Growth & Design
Abstract
Hydroxybenzoic acid is used in many applications, including medicine and polymer synthesis. The synthesis, self-assembly, and characterization of three pseudopolymorphs of a derivative of a widely used 4-hydroxybenzoic acid (1) are described in detail. In this investigation, we have incorporated hydrophobic (biphenyl groups) and hydrophilic (-OH and -CO2H) groups on an aromatic ring to influence the self-assembly in the solid lattice. Compound 1 crystallizes into three crystalline forms: (i) monoclinic from a solution of DMSO (1A), (ii) triclinic from a 1:1 solution of DMSO/hot ethyl acetate (1B), and (iii) triclinic from pyridine solution (1C). The formation of these pseudopolymorphs and the structural similarities in their packing motifs can be rationalized through a few multipoint solute−solvent interactions. In all three structures, the crystallographic aspects pertaining to the influence of solvent molecules towards the formation of hydrogen bonded network structures are described. In addition to th...