Abstract
The present study refers to the preparation of isonicotinic acid hydrazide (isoniazid (INH)) cocrystals with two α-hydroxycarboxylic acids. The interaction of glycolic acid (H2ga) or dl-mandelic acid (H2ma) resulted in the formation of cocrystals, or salts of composition, as isoniazid−glycolic acid cocrystal (INH)·(H2ga) (1) and isoniazid−dl-mandelic acid salt cocrystal [HINH]+[Hma]−·(H2ma) (2), when reacted with isoniazid. An N’-(propan-2-ylidene)isonicotinic hydrazide hemihydrate, (pINH)·1/2(H2O) (3), was also prepared by condensation of isoniazid with acetone in the presence of glycolic acid. The prepared compounds were well characterized by elemental analysis and spectroscopic methods, and their three-dimensional molecular structure was determined by single-crystal X-ray crystallography. Hydrogen bonds involving carboxylic acid occur consistently with the pyridine ring N atom of the isoniazid and its derivatives. The remaining hydrogen-bonding sites on the isoniazid backbone vary on the basis of the steric influences of the derivative group. These are contrasted in each of the molecular systems.
Highlights
As an important part of supramolecular chemistry, crystal engineering is the subject of continuous research in solid and materials science
Acid-base binary cocrystals is an important technological topic in pharmaceutical science that has attracted scientific and pharmaceutical interest in recent decades due to their potential ability to modify important properties of active pharmaceutical ingredients (APIs) such as solubility, dissolution rate, bioavailability, hygroscopicity, and/or thermal stability [2]. The formation of these multicomponent crystals does not lead to changes in the nature of the API, unlike the situation observed during salt formation, where the API must protonate or be protonated [3]
As possible coformers of salts or co-crystals against inh, we have considered αhydroxycarboxylic acids, glycolic (H2ga) and DL-mandelic (H2ma) (Scheme 1) [9,10]
Summary
As an important part of supramolecular chemistry, crystal engineering is the subject of continuous research in solid and materials science. As possible coformers of salts or co-crystals against inh, we have considered αhydroxycarboxylic acids, glycolic (H2ga) and DL-mandelic (H2ma) (Scheme 1) [9,10].
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