N-2-hydroxy-4-methoxyacetophenone-N'-4-nitrobenzoyl hydrazine: synthesis and structural characterization

A new aroyl hydrazone, N-2-hydroxy-4-methoxyacetophenone-N'-4-nitrobenzoyl hydrazine was prepared by the condensation reaction of 2-hydroxy-4-methoxyacetophenone and 4-nitrobenzoyl hydrazine. Characterization of the compound was done by elemental analysis and electronic, infrared and NMR spectral analyses. The complete structural assignment of the compound was done by NMR studies by using COSY homonuclear and HSQC heteronuclear techniques. The crystal and molecular structure was determined by single crystal X-ray diffraction studies: crystallized in the monoclinic system, space group P2(1)/n, Z=4, a=7.3343(9)A, b=20.3517(9)A, c=10.1375(5)A, alpha=90.00 degrees, beta=95.735(7) degrees and gamma=90.00 degrees. From the crystal structure, it is concluded that the compound exists as the keto isomer in the solid state. There is a completely extended conformation in the central part of the molecule C5C8N1N2C10O2 with an E configuration at the double bond of the hydrazinic bridge.