Synthesis, X-ray and spectroscopic analysis of 2-hydrazino-6-methyl-4-(methoxymethyl)-5-nitropyridine-3-carbonitrile

Abstract

Pyridine derivative 2-hydrazino-6-methyl-4-(methoxymethyl)-5-nitropyridine-3-carbonitrile ( 2) has been obtained from 2-chloro-4-(methoxymethyl)-6-methyl-5-nitropyridine-3-carbonitrile ( 1) by novel protocol and its structure was determined by X-ray diffraction method. An analysis revealed some structural differences in 2 compared to corresponding 3-cyano-5-nitro-pyridines and 2-hydrazinopyridines. Supramolecular structure contains one N H⋯N and two N H⋯O hydrogen bonds, as well as one C H⋯O hydrogen bond. Structural features have been also studied by FT-IR, FT-R and NMR spectroscopy. FT-IR dilution experiments showed that the character of intermolecular NH⋯O and NH⋯N interactions in solution depends on concentration. The spectral properties were investigated by UV–vis absorption and fluorescence spectroscopy techniques. Absorption spectra of compounds have been recorded in protic and aprotic solvents in the range 200–550 nm and solvent effects on the absorption spectra of this compound are interpreted. Absorption spectra of aqueous solution of compound 2 were also recorded at different temperatures and pH values and protonation constant was calculated. Unlike previously studied structurally similar compound 1, the title compound 2 does not emit fluorescence.