Structures of four organic acid-base adducts from 4-aminoantipyrine, 3,5-dinitrobenzoic acid, anthranilic acid, 5-nitrosalicylic acid, and 1, 5-naphthalenedisulfonic acid

Abstract

Cocrystallization of 4-aminoantipyrine which is widely used in the field of pharmacological applications with four organic acids yielded acid-base adducts: (4-aminoantipyrine): (3,5-dinitrobenzoic acid) [(HL+) · (dna−), dna− = 3,5-dinitrobenzoate] (1), (4-aminoantipyrine): (anthranilic acid) [(L) · (Hata), Hata = anthranilic acid] (2), (4-aminoantipyrine)2: (5-nitrosalicylic acid)3: H2O [(HL+)2 · (nsa−)2 · (Hnsa) · H2O, nsa− = 5-nitrosalicylate] (3) and (4-aminoantipyrine)2: (1,5-naphthalenedisulfonic acid) [(HL+)2 · (nds2−), nds2− = 1, 5-naphthalenedisulfonate] (4). The four adducts have been characterised by elemental analysis, infrared spectroscopy and X-ray single crystal diffraction, their melting points were also gauged. Their structural and supramolecular aspects are fully analyzed.XRD analysis indicated that 1, 3 and 4 are organic salts, 2 is a cocrystal. The crystal packing is mediated by the strong charge-assisted or neutral NH⋯O hydrogen bond. Apart from the NH⋯O hydrogen bonds, the OH···O hydrogen bonds are also present at 2–3. Further inspection into the crystal packing indicate that a different family of additional CH⋯O/CH3⋯O, CH⋯π/CH3⋯π and OH⋯π/O···π contacts contributes to the stabilization and expansion of the final 2D/3D structures.