Weak Interactions in Cocrystals of Isoniazid with Glycolic and Mandelic Acids

This work deals with the preparation of pyridine-3-carbohydrazide (isoniazid, inh) cocrystals two ?-hydroxycarboxylic acids. The interaction glycolic acid (H2ga) or d,l-mandelic (H2ma) resulted in formation salts composition (inh)·(H2ga) (1) and [Hinh]+[Hma]–·(H2ma) (2) when reacted isoniazid. An N?-(propan-2-ylidene)isonicotinic hydrazide hemihydrate, (pinh)·1/2(H2O) (3), was also prepared by condensation isoniazid acetone presence acid. These compounds were well characterized elemental analysis, spectroscopic methods, their three-dimensional molecular structure determined single crystal X-ray crystallography. Hydrogen bonds involving carboxylic occur consistently pyridine ring N atom its derivatives. remaining hydrogen-bonding sites on backbone vary based steric influences derivative group. are contrasted each systems. Finally, Hirshfeld surface analysis Density-functional theory (DFT) calculations (including NCIplot QTAIM analyses) have been performed to further characterize rationalize non-covalent interactions.