Synthesis, Characterization and Crystal Structures of 2-Cyano-N′-(2-chlorobenzylidene)acetohydrazide and 2-Cyano-N′-(4-dimethylaminobenzylidene)acetohydrazide

Abstract

Two new benzohydrazone derivatives, 2-cyano-N′-(2-chlorobenzylidene)acetohydrazide (1) and 2-cyano-N′-(4-dimethylaminobenzylidene)acetohydrazide (2), were prepared and characterized by elemental analysis, 1H and 13C NMR, and single crystal X-ray diffraction. Compound 1 crystallizes in the monoclinic space group P21/c with unit cell dimensions a = 9.925(1) A, b = 7.045(1) A, c = 15.117(2) A, β = 91.479(2)°, V = 1056.7(2) A3, Z = 4, R 1 = 0.0447, and wR 2 = 0.0930. Compound 2 crystallizes in the monoclinic space group P21/c with unit cell dimensions a = 13.714(2) A, b = 8.938(1) A, c = 10.883(1) A, β = 112.628(2)°, V = 1231.3(3) A3, Z = 4, R 1 = 0.0578, and wR 2 = 0.1122. X-ray diffraction indicated that the molecules of the compounds display trans configurations with respect to the C=N double bonds. The crystal structures of the compounds are stabilized by N–H···O hydrogen bonds and weak π···π interactions. Two new benzohydrazone derivatives, 2-cyano-N′-(2-chlorobenzylidene)acetohydrazide and 2-cyano-N′-(4-dimethylaminobenzylidene)acetohydrazide, were prepared and characterized by elemental analysis, 1H and 13C NMR, and single crystal X-ray diffraction. The molecules of the compounds display trans configurations with respect to the C=N double bonds. The crystal structures of the compounds are stabilized by N–H···O hydrogen bonds and weak π···π interactions.