A Tale of Two Stoichiometrically Diverse Cocrystals

Liquid-assisted grinding of an equimolar amount of pyrazinamide and p-nitrobenzoic acid yields two stoichiometric cocrystals in a 1:1 and 2:1 ratio, respectively. The 2:1 cocrystal was found to be the thermodynamically stable cocrystal based on solid stoichiometric interconversion, solvent-mediated conversion, and solubility studies.