Synthesis, Characterization and Crystal Structures of N,N'-bis(5-Fluoro-2-hydroxybenzylidene)-ethylenediamine and 4,4'-Difluoro-2,2'-[(hydrazine-1,2-diylidene)bis(methanylylidene)]diphenol

Wei-Ming Zhang; Shao-Song Qian; Zhonglu You

doi:10.14233/ajchem.2014.17999

Issue

Vol. 26 No. 22 (2014): Vol 26 Issue 22

Issue Published : November 6, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis, Characterization and Crystal Structures of N,N'-bis(5-Fluoro-2-hydroxybenzylidene)-ethylenediamine and 4,4'-Difluoro-2,2'-[(hydrazine-1,2-diylidene)bis(methanylylidene)]diphenol

https://doi.org/10.14233/ajchem.2014.17999

Wei-Ming Zhang

Nanjing Institute for the Comprehensive Utilization of Wild Plant, Nanjing 210042, P.R. China

Shao-Song Qian

School of Life Sciences, Shandong University of Technology, Zibo 255049, P.R. China

Zhonglu You

Department of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, P.R. China

Corresponding Author(s) : Wei-Ming Zhang

youzhonglu@126.com

Asian Journal of Chemistry, Vol. 26 No. 22 (2014): Vol 26 Issue 22
Article Published : November 6, 2014

Abstract

Two new bis-Schiff base compounds, N,N'-bis(5-fluoro-2-hydroxybenzylidene)-ethylenediamine (1) and 4,4'-difluoro-2,2'-[(hydrazine-1,2-diylidene)bis(methanyl-ylidene)]diphenol (2), were prepared and structurally characterized by elemental analysis, IR, ¹H NMR and UV-visible spectra and single crystal X-ray determination. Compound 1 crystallizes as monoclinic space group P2₁/n, with unit cell dimensions a = 7.227(2) Å, b = 10.970(3) Å, c = 9.973(2) Å, b = 104.913(2)º, V = 695.1(3) Å³, Z = 2, R₁ = 0.0893 and wR₂ = 0.2724. Compound 2 crystallizes as monoclinic space group P2₁/n, with unit cell dimensions a = 8.205(1) Å, b = 6.643(1) Å, c = 11.816(2) Å, b = 105.848(3)º, V = 619.6(1) Å³, Z = 2, R₁ = 0.0424 and wR₂ = 0.0879. Crystal of the compounds are stabilized by hydrogen bonds and p···p interactions.

Keywords

Schiff base Crystal structure Hydrogen bonding π···π interaction

Zhang, W.-M., Qian, S.-S., & You, Z. (2014). Synthesis, Characterization and Crystal Structures of N,N’-bis(5-Fluoro-2-hydroxybenzylidene)-ethylenediamine and 4,4’-Difluoro-2,2’-[(hydrazine-1,2-diylidene)bis(methanylylidene)]diphenol. Asian Journal of Chemistry, 26(22), 7843–7845. https://doi.org/10.14233/ajchem.2014.17999

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References

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References

R.P. Saini, V. Kumar, A.K. Gupta and G.K. Gupta, Med. Chem. Res., 23, 690 (2014); doi:10.1007/s00044-013-0657-6.

F. Zhang, Q. Wen, S.-F. Wang, B. Shahla Karim, Y.-S. Yang, J.-J. Liu, W.-M. Zhang and H.-L. Zhu, Bioorg. Med. Chem. Lett., 24, 90 (2014); doi:10.1016/j.bmcl.2013.11.079.

M.M. Kamel, H.I. Ali, M.M. Anwar, N.A. Mohamed and A.M. Soliman, Eur. J. Med. Chem., 45, 572 (2010); doi:10.1016/j.ejmech.2009.10.044.

S.J. Ren, R. Wang, K. Komatsu, P. Bonaz-Krause, Y. Zyrianov, C.E. McKenna, C. Csipke, Z.A. Tokes and E.J. Lien, J. Med. Chem., 45, 410 (2002); doi:10.1021/jm010252q.

P. Sambasiva Rao, C. Kurumurthy, B. Veeraswamy, G. Santhosh kumar, B. Narsaiah, K. Pranay Kumar, U.S.N. Murthy, S. Karnewar and S. Kotamraju, Med. Chem. Res., 22, 1747 (2013); doi:10.1007/s00044-012-0168-x.

S.H. Sumrra and Z.H. Chohan, J. Enzyme Inhib. Med. Chem., 28, 1291 (2013); doi:10.3109/14756366.2012.735666.

J.-Q. Ren, Q.-Z. Jiao, Y.-N. Wang, F.-Y. Xu, X.-S. Cheng and Z.-L. You, Wuji Huaxue Xuebao, 30, 640 (2014).

J.-C. Zhang, Y.-N. Li, D. Huang, F.-Y. Xu, X.-S. Cheng and Z.-L. You, Wuji Huaxue Xuebao, 30, 425 (2014).

X.-S. Zhou, Z.-L. You, D.-M. Xian and D.-P. Dong, Wuji Huaxue Xuebao, 29, 850 (2013).

Z.-L. You, X.-Y. Qiu, D.-M. Xian and M. Zhang, Inorg. Chem. Commun., 26, 11 (2012); doi:10.1016/j.inoche.2012.09.014.

Z.-L. You, D.-M. Xian and M. Zhang, CrystEngComm, 14, 7133 (2012); doi:10.1039/c2ce26201k.

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.

D.J. Darensbourg and D.R. Billodeaux, Inorg. Chem., 44, 1433 (2005); doi:10.1021/ic048508g.

A. Davis, C.A. Kilner and T.P. Kee, Inorg. Chim. Acta, 357, 3493 (2004); doi:10.1016/j.ica.2004.01.048.

Issue

Vol. 26 No. 22 (2014): Vol 26 Issue 22

Synthesis, Characterization and Crystal Structures of N,N'-bis(5-Fluoro-2-hydroxybenzylidene)-ethylenediamine and 4,4'-Difluoro-2,2'-[(hydrazine-1,2-diylidene)bis(methanylylidene)]diphenol

Corresponding Author(s) : Wei-Ming Zhang

Abstract

Keywords

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