Mefenamic acid (MA) formed solvates with 2-picoline (2PIC), 3-picoline (3PIC), 4-picoline (4PIC) and 3-chloropyridine (3CLPYR). The solvates crystallized in the space group P\bar 1 with the carboxylic acid of MA hydrogen-bonded to the nitrogen of the substituted pyridine. Tolfenamic acid (TFA) formed solvates with 2PIC and 3PIC, the crystal structures successfully solved in the space groups P21/n and Pbca, respectively. The fenamate conformation varied depending on the acid and the included solvent. Similarities were observed in the structures involving MA. The two solvate structures of TFA had different packing arrangements. Grinding and slurry experiments were also successful for the preparation of all of the compounds except MA·2PIC. Recrystallization, grinding and slurry investigations of MA and 2PIC yielded a polymorph; the structure was successfully solved in P21/n. Additionally, the thermal stability of the solvates was determined. Desolvation experiments were also performed and the resultant powders were analysed using powder X-ray diffraction.
Keywords: desolvation; fenamic acids; kinetics; picolines; polymorphism.