N-2-Hydroxy-4-methoxyacetophenone- N′-4-nitrobenzoyl hydrazine: Synthesis and structural characterization

• Published in: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy Molecular and biomolecular spectroscopy, 2007-04, Vol.66 (4), p.898-903
• Main Authors: Bessy Raj, B.N., Kurup, M.R. Prathapachandra
• Format: Article
• Language: English
• Subjects: Acetophenones - chemical synthesis; Acetophenones - chemistry; Aroylhydrazone; COSY; Crystal studies; Crystallography, X-Ray; HSQC; Hydrazines - chemical synthesis; Hydrazines - chemistry; Hydrogen Bonding; Magnetic Resonance Spectroscopy; Spectrophotometry, Infrared
• ISSN: 1386-1425
• DOI: 10.1016/j.saa.2006.05.006

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) Å, b = 20.3517(9) Å, c = 10.1375(5) Å, α = 90.00°, β = 95.735(7)° and γ = 90.00°. 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 C5 C8 N1 N2 C10 O2 with an E configuration at the double bond of the hydrazinic bridge.