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

• Published in: Journal of chemical crystallography Vol. 42; no. 11; pp. 1138 - 1141
• Main Authors: Zhou, Xin, Ma, Jing-Jun
• Format: Journal Article
• Language: English
• Published: Boston Springer US 01.11.2012
• Subjects: Chemistry; Chemistry and Materials Science; Crystallography and Scattering Methods; Inorganic Chemistry; Organometallic Chemistry; Original Paper; Physical Chemistry; X-ray diffraction; Benzohydrazone; Synthesis; Hydrogen bonding; Crystal structure
• ISSN: 1074-1542; 1572-8854
• DOI: 10.1007/s10870-012-0372-z

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, 1 H and 13 C NMR, and single crystal X-ray diffraction. Compound 1 crystallizes in the monoclinic space group P 2 1 / c with unit cell dimensions a  = 9.925(1) Å, b  = 7.045(1) Å, c  = 15.117(2) Å, β  = 91.479(2)°, V  = 1056.7(2) Å 3 , Z  = 4, R 1  = 0.0447, and wR 2  = 0.0930. Compound 2 crystallizes in the monoclinic space group P 2 1 / c with unit cell dimensions a  = 13.714(2) Å, b  = 8.938(1) Å, c  = 10.883(1) Å, β  = 112.628(2)°, V  = 1231.3(3) Å 3 , 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. Index Abstract Two new benzohydrazone derivatives, 2-cyano- N ′-(2-chlorobenzylidene)acetohydrazide and 2-cyano- N ′-(4-dimethylaminobenzylidene)acetohydrazide, were prepared and characterized by elemental analysis, 1 H and 13 C 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.