JCPT  Vol.3 No.2 , April 2013
Synthesis, Spectral Characterization and Crystal Structure of 2-((3-Aminophenyl)(phenyl)methylene) hydrazinecarboxamide
ABSTRACT

A benzophenone substituted semicarbazone, 2-((3-aminophenyl)(phenyl)methylene)hydrazinecarboxamide (APHC) had been synthesized in good yield by the condensation of 3-aminobenzophenone and semicarbazide hydrochloride. The title compound was elucidated by elemental analysis (CHN), FTIR, 1H and 13C-NMR, 1H-1H COSY, TGA and single crystal X-ray diffraction. The compound crystallized in the orthorhombic crystal system with space group of Pccn, Z = 32, V = 10375.1 (2) ?3, and lattice constants a = 12.3855 (1) ?, b = 34.5746 (5) ?, c = 24.2283 (3) ? and γ = β = α = 90°. The molecular view shows that APHC contains four molecules of each species in the asymmetric unit, with similar geometries. However, there is no intramolecular hydrogen bond found in the crystal structure of the synthesized compound. X-ray diffraction also reveals that the molecule of the semicarbazone exists as a Z isomer with respect to the C=N.


Cite this paper
Y. Chan, A. Ali, M. Khairuddean and C. Quah, "Synthesis, Spectral Characterization and Crystal Structure of 2-((3-Aminophenyl)(phenyl)methylene) hydrazinecarboxamide," Journal of Crystallization Process and Technology, Vol. 3 No. 2, 2013, pp. 64-68. doi: 10.4236/jcpt.2013.32010.
References
[1]   S. N. Pandeya, P. Yogeeswari and J. P. Stables, “Synthesis and Anticonvulsant Activity of 4-Bromophenyl Substituted Aryl Semicarbazones,” European Journal of Medicinal Chemistry, Vol. 35, No. 10, 2000, pp. 879-886. doi:10.1016/S0223-5234(00)01169-7

[2]   S. N. Pandeya, V. Mishra, P. N. Singh and D. C. Rupainwar, “Anticonculsant Activity of Thioureido Derivatives of Acetophenone Semicarbazone,” Pharmacological Research, Vol. 37, No. 1, 1998, pp. 17-22. doi:10.1006/phrs.1997.0250

[3]   T. Hemalatha, P. K. M. Imran, A. Gnanamani and S. Nagarajan, “Synthesis, Antibacterial and Antifungal Activities of Some N-nitroso-2,6-diarylpiperidin-4-one Semicarbazones and QSAR Analysis,” Nitric Oxide, Vol. 19, No. 4, 2008, pp. 303-311. doi:10.1016/j.niox.2008.07.006

[4]   M. J. Ahsan, J. G. Samy, H. Khalilullah and M. S. Nomani, “Semicarbazone Analogues: A Mini Review,” Der Pharmacia Sinica, Vol. 2, No. 6, 2011, pp. 107-113.

[5]   K. Alomar, V. Gaumet, M. Allain, G. Bouet and A. Landreau, “Synthesis, Crystal Structure, Characterization, and Antifungal Activity of 3-Thiophene Aldehyde Semicarbazone (3STCH), 2,3-Thiophene Dicarboxaldehyde Bis (Semicarbazone) (2,3BSTCH2) and Their Nickel (II) Complexes,” Journal of Inorganic Biochemistry, Vol. 115, 2012, pp. 36-43. doi:10.1016/j.jinorgbio.2012.04.022

[6]   D. S. Raja, N. S. P. Bhuvanesh and K. Natarajan, “Effect of N(4)-Phenyl Substitution in 2-Oxo-1,2-dihydroquinoline-3-carbaldehyde Semicarbazones on the Structure, DNA/Protein Interaction, and Antioxidative and Cytotoxic Activity of Cu(II) Complexes,” Inorganic Chemistry, Vol. 50, No. 24, 2011, pp. 12852-12866. doi:10.1021/ic2020308

[7]   S. Shukla, R. S. Srivastava, S. K. Shrivastava, A. Sodhi and P. Kumar, “Synthesis, Molecular Docking and Biological Evaluation of 4-Cycloalkylidineamino 1, 2-Naphthoquinone Semicarbazones as Anticancer agents,” Asian Pacific Journal of Tropical Biomedicine, Vol. 2, No. 2, 2012, pp. S1040-S1046. doi:10.1016/S2221-1691(12)60358-X

[8]   A. P. Gulya, D. Gynzhu, N. N. Bairak, D. Poirier and V. I. Tsapkov, “Synthesis, Structure and Properties of Complex Compounds of Cobalt, Nickel, Copper and Zinc with 2-Formylpyridine Semicarbazone,” Russian Journal of General Chemistry, Vol. 79, No. 7, 2009, pp. 1499-1503. doi:10.1134/S1070363209070160

[9]   J. D. Patel and P. J. Shah, “Synthesis, Characterization and Chelating Properties of 4-Butyrylsemicarbazone-1- phenyl-3-methyl-2-pyrazolin-5-one,” E-Journal of Chemistry, Vol. 7, No. 2, 2010, pp. 357-362.

[10]   R. Sharma, S. K. Argawal, S. Rawat and M. Nagar, “Syntheis, Characterization and Antibacterial Activity of Some Transition Metal Cis-3,7-dimethyl-2, 6-octadiensemicarbazone Complexes,” Transition Metal Chemistry, Vol. 31, No. 2, 2006, pp. 201-206. doi:10.1007/s11243-005-6374-3

[11]   J. Cosier and A. M. Glazer, “A Nitrogen-Gas-Stream Cryostat for General X-ray Diffraction Studies,” Journal of Applied Crystallography, Vol. 19, No. 2, 1986, pp. 105-107. doi:10.1107/S0021889886089835

[12]   Bruker, “APEX2, SAINT and SADABS,” Bruker AXS Inc., Madison, 2009.

[13]   G. M. Sheldrick, “A Short History of SHELX,” Acta Crystallographica Section A, Vol. 64, No. 1, 2008, pp. 112-122.

[14]   J. Bernstein, R. E. Davis, L. Shimoni and N.-L. Chang, “Patterns in Hydrogen Bonding: Functionality and Graph Set Analysis in Crystals,” Angewandte Chemie International Edition in English, Vol. 34, No. 15, 1995, pp. 1555-1573. doi:10.1002/anie.199515551

[15]   P. Souza, J. M. Merino, V. Fernández and A. Arquero, “Solvent and Metal Ion Effects in Condensation Reactions between Semicarbazides and Pyridine Derivatives and Study of the Complexes with Metal Chlorides,” Transition Metal Chemistry, Vol. 17, No. 4, 1992, pp. 338- 342.

[16]   E. N. Nfor, S. N. Esemu, G. A. Ayimele, E. A. Eno, G. E. Iniama and O. E. Offiong, “Synthesis, Stereochemistry and Antimicrobial Activity of Copper (II) and Nickel (II) Complexes of 4-Phenylsemicarbazones,” Bulletin of Chemical Society of Ethiopia, Vol. 25, No. 3, 2011, pp. 361-370.

[17]   U. El-Ayaan, “Transition Metal Complexes of 3-Acetylpyridine 4N-(2-pyridyl)thiosemicarbazone (HAPS); Structural, Spectroscopic, and Biological Studies,” Journal of Coordination Chemistry, Vol. 65, No. 4, 2012, pp. 629-642. doi:10.1080/00958972.2012.658381

 
 
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