SYNTHESIS, CRYSTAL STRUCTURE, SPECTROSCOPIC AND COMPUTATIONAL STUDIES OF 2-{1-2-(1,3-DIMETHYL-4-NITRO-1H-PYRAZOL-5-YL)HYDRAZONOETHYL}PYRIDINE

摘要

2-{1-2-(1,3-Dimethyl-4-nitro-1H-pyrazol-5-ylhydrazonoethyl}-pyridine has been prepared from 5-hydrazino-1,3-dimethy1-4-nitro-1H-pyrazole and 2-acetylpyridine in an ethanolic solution. It crystallizes as an (E/Z) isomeric pair in the triclinic space group P-1 with the lattice parameters: a = 10.357(1) angstrom, b = 11.613(1) angstrom, c = 13.069(1) angstrom, alpha = 67.74(1)degrees, beta = 70.77(1)degrees, gamma = 67.92(1)degrees, volume = 1315.6(3) angstrom(3), Z = 2. The isomeric pair (E/Z) is contained in the unit cell, where the N-H group is H-bonded to the pyridine nitrogen and to the oxygen of the nitro group in the Z-isomer and to the oxygen of the nitro group only in the E-isomer. NMR showed that the E-isomer is the major. DFT calculations were performed to further investigate the electronic properties of the synthesized compound.