Synthesis, Characterization and Crystal Structure of trans-2-(2-Hydroxyphenyl)-1-nitroethylene

Yun-Feng Liu; Sheng-Nan Liu; Pei-Hua Zhao; Xin-Hang Li; Wen-Jun Liang; Ya-Qing Liu

doi:10.14233/ajchem.2014.16446

Issue

Vol. 26 No. 8 (2014): Vol 26 Issue 8

Issue Published : April 15, 2014

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

Synthesis, Characterization and Crystal Structure of trans-2-(2-Hydroxyphenyl)-1-nitroethylene

https://doi.org/10.14233/ajchem.2014.16446

Yun-Feng Liu

College of Public Health, Shanxi Medical University, Taiyuan 030001, P.R. China

Sheng-Nan Liu

Research Center for Engineering Technology of Polymeric Composites of Shanxi Province, College of Materials Science and Engineering, North University of China, Taiyuan 030051, P.R. China

Pei-Hua Zhao

Research Center for Engineering Technology of Polymeric Composites of Shanxi Province, College of Materials Science and Engineering, North University of China, Taiyuan 030051, P.R. China

Xin-Hang Li

Research Center for Engineering Technology of Polymeric Composites of Shanxi Province, College of Materials Science and Engineering, North University of China, Taiyuan 030051, P.R. China

Wen-Jun Liang

Research Center for Engineering Technology of Polymeric Composites of Shanxi Province, College of Materials Science and Engineering, North University of China, Taiyuan 030051, P.R. China

Ya-Qing Liu

Research Center for Engineering Technology of Polymeric Composites of Shanxi Province, College of Materials Science and Engineering, North University of China, Taiyuan 030051, P.R. China

Corresponding Author(s) : Pei-Hua Zhao

zph2004@163.com, gczx2012@gmail.com

Asian Journal of Chemistry, Vol. 26 No. 8 (2014): Vol 26 Issue 8
Article Published : April 16, 2014

Abstract

The nitroalkene compound, namely trans-2-(2-hydroxyphenyl)-1-nitroethylene (I), has been successfully synthesized from the condensation of 2-hydroxybenzaladehyde with nitromethane. It was characterized by elemental analysis, ¹H NMR spectrum and single-crystal X-ray diffraction analysis. Compound (I) crystallizes in the triclinic, space group P-1 with a = 5.2270(5), b = 11.2130(10), c = 13.6080(13) Å, a = 71.224(18), b = 84.47(3), g = 81.20(3)°, V = 745.29(16) Å3, Z = 4, C₈H₇NO₃, M_r = 165.15, D_c = 1.472 g/cm³, F(000) = 344, μ(MoK_a) = 0.115 mm^-1, the final R₁ = 0.0500 and wR₂ = 0.1358 for 2309 observed reflections [I > 2s(I)]. Moreover, the crystal structure of (I) is stabilized by the intermolecular O-H···O hydrogen bonds, the p-p stacking interactions and the C-H···O short contacts, which extend the molecules into an infinite three-dimensional network.

Keywords

Nitroalkene Synthesis Crystal Structure Intermolecular interaction

Liu, Y.-F., Liu, S.-N., Zhao, P.-H., Li, X.-H., Liang, W.-J., & Liu, Y.-Q. (2014). Synthesis, Characterization and Crystal Structure of trans-2-(2-Hydroxyphenyl)-1-nitroethylene. Asian Journal of Chemistry, 26(8), 2475–2478. https://doi.org/10.14233/ajchem.2014.16446

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References

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R. Ballini, G. Bosica, D. Fiorini, A. Palmieri and M. Petrini, Chem. Rev., 105, 933 (2005); doi:10.1021/cr040602r.

M. Bakthadoss, N. Sivakumar, A. Devaraj and D.S. Sharada, Synthesis, 2136 (2011); doi:10.1055/s-0030-1260053.

C. Czekelius and E.M. Carreira, Angew. Chem. Int. Ed., 44, 612 (2005); doi:10.1002/anie.200461879.

Z. Zheng, B.L. Perkins and B. Ni, J. Am. Chem. Soc., 132, 50 (2010); doi:10.1021/ja9093583.

Y. Zhu, J.P. Malerich and V.H. Rawal, Angew. Chem. Int. Ed., 49, 153 (2010); doi:10.1002/anie.200904779.

N. Latif, N. Mishriky, N.S. Girgis and S. Arnos, Indian J. Chem., 19B, 301 (1980).

R. Mohan, N. Rastogi, I.N.N. Namboothiri, S.M. Mobin and D. Panda, Bioorg. Med. Chem., 14, 8073 (2006); doi:10.1016/j.bmc.2006.07.035.

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P.H. Zhao, Z.H. Feng, M. Zhang, Y.Q. Liu and G.Z. Zhao, Acta Crystallogr. Sect. E Struct. Rep. Online, 67, o3505 (2011); doi:10.1107/S1600536811050963.

P.H. Zhao, E.J. Hao, Y.Q. Liu and G.Z. Zhao, Acta Cryst., E68, o1742 (2012); doi:10.1107/S1600536812020806.

P.H. Zhao, M. Zhang and G.Z. Zhao, Asian J. Chem., 25, 5068 (2013); doi:10.14233/ajchem.2013.14513.

P.H. Zhao and Y.F. Liu, Mol. Cryst. Liq. Cryst., 587, 113 (2013); doi:10.1080/15421406.2013.821645.

G.M. Sheldrick, SHELXS97, A Program for Crystal Structure Solution, University of Göttingen: Germany (1997).

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T.S. Cameron, D.J. Cowley and J.E. Thompson, J. Chem. Soc. Perkin Trans. II, 774 (1974); doi:10.1039/p29740000774.

P.Q. Chen, C.X. Tan, J.Q. Weng and X.H. Liu, Asian J. Chem., 24, 2808 (2012).

M.J.S. Dewar and W. Thiel, J. Am. Chem. Soc., 99, 4907 (1977); doi:10.1021/ja00457a005.

V.N. Nesterov, V.P. Kislyi, T.V. Timofeeva, M.Y. Antipin and V.V. Semenov, Acta Crystallogr. C, 56, e107 (2000); doi:10.1107/S0108270100001864.

E.J. Hao, Y.F. Liu, L.F. Han and J.L. Zhang, Asian J. Chem., 25, 9975 (2013); doi:10.14233/ajchem.2013.15790.

Issue

Vol. 26 No. 8 (2014): Vol 26 Issue 8

Synthesis, Characterization and Crystal Structure of trans-2-(2-Hydroxyphenyl)-1-nitroethylene

Corresponding Author(s) : Pei-Hua Zhao

Abstract

Keywords

Full Article

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