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Synthesis, Crystal Structures and Antimicrobial Activities of N'-[4-(Dimethylamino)benzylidene]-2-hydroxy-3-methylbenzohydrazide Monohydrate and N'-(4-Nitrobenzylidene)-2-hydroxy-3-methylbenzohydrazide Monohydrate
Corresponding Author(s) : Peifeng Yin
Asian Journal of Chemistry,
Vol. 26 No. 18 (2014): Vol 26 Issue 18
Abstract
Two structural similar hydrazone compounds, N'-[4-(dimethylamino)benzylidene]-2-hydroxy- 3-methylbenzohydrazide monohydrate (1) and N'-(4-nitrobenzylidene)-2-hydroxy-3- methylbenzohydrazide monohydrate (2), have been synthesized and structurally characterized by elemental analysis, IR spectra, 1H NMR and X-ray single crystal structure determinations. Both compounds crystallize in monoclinic space group P21/c. X-ray crystallography reveals that each compound consists of a hydrazone molecule and a water molecule of crystallization. The molecule of each compound has E configurations with respect to the C=N double bond and C-N single bond. The water molecules are linked to the hydrazone molecules through intramolecular O-H···O and O-H···N hydrogen bonds. In the crystal structures of both compounds, molecules are linked through intermolecular O-H···O and N-H···O hydrogen bonds, forming layers parallel to ac plane. Antimicrobial activities against Bacillus subtilis, Escherichia coli, Staphyloccocus aureus and Bacillus magaterium were studied.
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- N. Sari, D. Nartop, F. Karci and A. Disli, Asian J. Chem., 20, 1975 (2008).
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- J.-G. Yang and F.-Y. Pan, Acta Crystallogr., E60, o2009 (2004); doi:10.1107/S1600536804024614.
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References
N. Sari, D. Nartop, F. Karci and A. Disli, Asian J. Chem., 20, 1975 (2008).
M.M. Hania, Asian J. Chem., 14, 1074 (2002).
M. Zhang, D.-M. Xian, H.-H. Li, J.-C. Zhang and Z.-L. You, Aust. J. Chem., 65, 343 (2012); doi:10.1071/CH11424.
A. Cukurovali, İ. Yilmaz, S. Gur and C. Kazaz, Eur. J. Med. Chem., 41, 201 (2006); doi:10.1016/j.ejmech.2005.01.013.
S.G. Küçükgüzel, A. Mazi, F. Sahin, S. Ozturk and J. Stables, Eur. J. Med. Chem., 38, 1005 (2003); doi:10.1016/j.ejmech.2003.08.004.
K.P. Deepa, K.K. Aravindakshan and F. Suhara, Asian J. Chem., 13, 513 (2001).
J.-G. Yang and F.-Y. Pan, Acta Crystallogr., E60, o2009 (2004); doi:10.1107/S1600536804024614.
F. Magirius, A. Linden and H. Heimgartner, Helv. Chim. Acta, 76, 1980 (1993); doi:10.1002/hlca.19930760517.
G.M. Sheldrick, SADABS Program for Empirical Absorption Correction of Area Detector, University of Göttingen, Germany (1996).
G.M. Sheldrick, SHELXTL V5.1. Software Reference Manual; Bruker AXS, Inc: Madison, Wisconsin, USA (1997).
F.H. Allen, O. Kennard, D.G. Watson, L. Brammer, A.G. Orpen and R. Taylor, J. Chem. Soc., Perkin Trans. II, S1 (1987); doi:10.1039/P298700000S1.
A. Barry, Procedures and Theoretical Considerations for Testing Antimicrobial Agents in Agar Media; In: Lorian (Ed.), Antibiotics in Laboratory Medicine, Williams and Wilkins, edn 5, Baltimore (1991).
T. Rosu, M. Negoiu, S. Pasculescu, E. Pahontu, D. Poirier and A. Gulea, Eur. J. Med. Chem., 45, 774 (2010); doi:10.1016/j.ejmech.2009.10.034.