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Synthesis, Characterization and Crystal Structures of Hydrazone Compounds Derived from Cyanoacetohydrazide
Corresponding Author(s) : Wei-Ming Zhang
Asian Journal of Chemistry,
Vol. 26 No. 22 (2014): Vol 26 Issue 22
Abstract
Two new hydrazone compounds, 2-cyano-N'-(3-ethoxy-2-hydroxybenzylidene)acetohydrazide (1) and 2-cyano-N'-(2-methoxybenzylidene)-acetohydrazide (2), were prepared and structurally characterized by elemental analysis, IR and UV-visible spectra and single crystal X-ray determination. Compound 1 crystallizes as monoclinic space group P21/c, with unit cell dimensions a = 19.573(7) Å, b = 9.620(4) Å, c = 13.731(5) Å, b = 110.372(4)º, V = 2423.8(15) Å3, Z = 8, R1 = 0.1047 and wR2 = 0.2767. Compound 2 crystallizes as monoclinic space group P21/c, with unit cell dimensions a = 4.503(2) Å, b = 10.066(3) Å, c = 24.435(3) Å, b = 95.29(2)º, V = 1103.0(5) Å3, Z = 4, R1 = 0.0430 and wR2 = 0.0978. Crystal of the compounds are stabilized by hydrogen bonds and p···p interactions.
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- D.W. Banner and P. Hadvary, J. Biol. Chem., 266, 20085 (1991).
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References
D.W. Banner and P. Hadvary, J. Biol. Chem., 266, 20085 (1991).
E. Sandstrom, Drugs, 38, 417 (1989); doi:10.2165/00003495-198938030-00005.
P.H. Chan, J.W. Schmidley, R.A. Fishman and S.M. Longar, Neurology, 34, 315 (1984); doi:10.1212/WNL.34.3.315.
H.S.D. Naeff, M.C.R. Franssen and H.C. van der Plas, Recl. Trav. Pay-B, 110, 139 (1991); doi:10.1002/recl.19911100502.
P. Pacher, A. Nivorozhkin and C. Szabo, Pharmacol. Rev., 58, 87 (2006); doi:10.1124/pr.58.1.6.
A.A. Fatokun, T.W. Stone and R.A. Smith, Neurosci. Lett., 416, 34 (2007); doi:10.1016/j.neulet.2007.01.078.
R.K. Robins, G.R. Revankar, D.E. O’Brien, R.H. Springer, T.N.A. Albert, K. Senga, J.P. Miller and D.G. Streeter, J. Heterocycl. Chem., 22, 601 (1985); doi:10.1002/jhet.5570220303.
K. Okamoto, B.T. Eger, T. Nishino, E.F. Pai and T. Nishino, Nucleos. Nucleot. Nucl. Acids, 27, 888 (2008); doi:10.1080/15257770802146577.
A. Haberland, H. Luther and I. Schimke, Agents Actions, 32, 96 (1991); doi:10.1007/BF01983326.
M.F. Simeonov, F. Fulop, R. Sillanpaa and K. Pihlaja, J. Org. Chem., 62, 5089 (1997); doi:10.1021/jo962323c.
S. Ianelli and M. Carcelli, J. Chem. Crystallogr., 31, 123 (2001); doi:10.1023/A:1014362502709.
R. Dinda, P. Sengupta, S. Ghosh, H. Mayer-Figge and W.S. Sheldrick, J. Chem. Soc., Dalton Trans., 4434 (2002); doi:10.1039/b207129k.
S.-P. Guo, Chinese J. Struct. Chem., 31, 377 (2012).
L. Somogyi and A.C. Benyei, Heteroatom Chem., 20, 183 (2009); doi:10.1002/hc.20531.
X. Zhou and J.-J. Ma, J. Chem. Crystallogr., 42, 1138 (2012); doi:10.1007/s10870-012-0372-z.
Bruker, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA (2002).
G.M. Sheldrick, SADABS. Program for Empirical Absorption Correction of Area Detector, University of Göttingen, Germany (1996).
G.M. Sheldrick, Acta Crystallogr. A, 64, 112 (2008); doi:10.1107/S0108767307043930.