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Synthesis and Crystal Structure of bis[4-(Imidazol-1-yl)phenyl]methane
Corresponding Author(s) : Kun Huang
Asian Journal of Chemistry,
Vol. 26 No. 7 (2014): Vol 26 Issue 7
Abstract
A bidentate imidazole derivative with the molecular formula C19H16N4, has been synthesized according to modified Ullmann-type coupling method involving C-N coupling reaction under the catalysis of copper and characterized by the 1H NMR, 13C NMR, elemental analysis and X-ray single-crystal diffraction. In the crystal structure, the two mean plans of benzene rings make dihedral angels of 83.05 (0.07)°. N-H···N hydrogen bonds link the molecules into a 1D supramolecular structure. In addition, weak C-H···p(Ph) stacking interactions are also observed.
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References
Z. Jin, Z. Li and R. Huang, Nat. Prod. Rep., 19, 454 (2002); doi:10.1039/b108923b.; J.Z. Ho, R.M. Mohareb, J.H. Ahn, T.B. Sim and H. Rapoport, J. Org. Chem., 68, 109 (2003); doi:10.1021/jo020612x.
M. Voets, I. Antes, C. Scherer, U. Müller-Vieira, K. Biemel, S. Marchais-Oberwinkler and R.W. Hartmann, J. Med. Chem., 49, 2222 (2006); doi:10.1021/jm060055x.; T. Wiglenda, I. Ott, B. Kircher, P. Schumacher, D. Schuster, T. Langer and R. Gust, J. Med. Chem., 48, 6516 (2005); doi:10.1021/jm050190u.
R.B. Bambal and R.P. Hanzlik, Chem. Res. Toxicol., 8, 729 (1995); doi:10.1021/tx00047a013.
H. Zhang, Q. Cai and D. Ma, J. Org. Chem., 70, 5164 (2005); doi:10.1021/jo0504464.
A. Rit, T. Pape, A. Hepp and F.E. Hahn, Organometallics, 30, 334 (2011); doi:10.1021/om101102j.; V. Nair, S. Bindu and V. Sreekumar, Angew. Chem. Int. Ed., 43, 5130 (2004); doi:10.1002/anie.200301714.
M.J. Earle and K.R. Seddon, Pure Appl. Chem., 72, 1391 (2000); doi:10.1351/pac200072071391.; W. Bao, Z. Wang and Y.J. Li, J. Org. Chem., 68, 591 (2003); doi:10.1021/jo020503i.
H.W. Guo, Y. Jin, F.M. Jian, Y.Y. Liu, S.L. Li and L.P. Zhang, Dalton Trans., 3080 (2008); doi:10.1039/B716657E.
Y. Zhu, W.Y. Wang, M.W. Guo, G. Li and H.J. Lu, Inorg. Chem. Commun., 14, 1432 (2011); doi:10.1016/j.inoche.2011.05.039.; J.R. Long and O.M. Yaghi, Chem. Soc. Rev., 38, 1213 (2009); doi:10.1039/b903811f.
W.B. Austin, N. Bilow, W.J. Kelleghan and K.S.Y. Lau, J. Org. Chem., 46, 2280 (1981); doi:10.1021/jo00324a015.
W. Wei, Y.C. Qin, M.M. Luo, P.F. Xia and M.S. Wong, Organometallics, 27, 2268 (2008); doi:10.1021/om800007s.
G.M. Sheldrick, SHELXTL97, Program for the Refinement of Crystal Structure, University of Göttingen, Germany (1997).