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Synthesis and Structural Characterization of Bromo-Substituted Salamo-Type Bisoximes Based on Bis(aminooxy)alkane and 3,5-Dibromosalicylaldehyde
Corresponding Author(s) : W.-K. Dong
Asian Journal of Chemistry,
Vol. 27 No. 2 (2015): Vol 27 Issue 2
Abstract
A series of bromo-substituted Salamo-type bisoximes H2L1-H2L3 have been synthesized through condensation reactions of 3,5-dibromosalicylaldehyde with 1,2-bis(aminooxy)ethane, 1,3-bis(aminooxy)propane and 1,4-bis(aminooxy)butane in ethanol medium, respectively and characterized by elemental analyses, IR and 1H NMR spectra. In the crystal structure of Salamo-type bisoximes H2L1, an infinite 1D supramolecular double chain-like structure is formed by intramolecular hydrogen bonds, p···p stacking interactions and intermolecular Br···Br halogen bondings.
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- D.J. Zhou, Q. Li, C.H. Huang, U. Shigeo, M. Masakazu, L.M. Ying and A.C. Yu, Polyhedron, 16, 1381 (1998); doi:10.1016/S0277-5387(96)00382-8.
- M.J. Kharodawala and A.K. Rana, Synth. React. Inorg. Met.-Org. Chem, 33, 1483 (2003); doi:10.1081/SIM-120024324.
- S. Akine, T. Taniguchi and T. Nabeshima, Angew. Chem. Int. Ed., 41, 4670 (2002); doi:10.1002/anie.200290011.
- M.F. Braña, A. Gradillas, A.G. Ovalles, B. López, N. Acero, F. Llinares and D.M. Mingarro, Bioorg. Med. Chem., 14, 9 (2006); doi:10.1016/j.bmc.2005.09.059.
- S. Akine, T. Taniguchi, W. Dong, S. Masubuchi and T. Nabeshima, J. Org. Chem., 70, 1704 (2005); doi:10.1021/jo048030y.
- M. Sasaki, K. Manseki, H. Horiuchi, M. Kumagai, M. Sakamoto, H. Sakiyama, Y. Nishida, M. Sakai, Y. Sadaoka, M. Ohba and H. Okawa, J. Chem. Soc., Dalton Trans., 259 (2000); doi:10.1039/a907423f.
- S.S. Sun, C.L. Stern, S.T. Nguyen and J.T. Hupp, J. Am. Chem. Soc., 126, 6314 (2004); doi:10.1021/ja037378s.
- J.C.G. Bünzli and C. Piguet, Chem. Rev., 102, 1897 (2002); doi:10.1021/cr010299j.
- S. Akine, T. Taniguchi and T. Nabeshima, Chem. Lett., 30, 682 (2001); doi:10.1246/cl.2001.682.
- S. Akine, W.K. Dong and T. Nabeshima, Inorg. Chem., 45, 4677 (2006); doi:10.1021/ic060055n.
- (a) S. Akine, Y. Morita, F. Utsuno and T. Nabeshima, Inorg. Chem., 48, 10670 (2009); doi:10.1021/ic901372k; (b) W.K. Dong, X.N. He, H.B. Yan, Z.W. Lv, X. Chen, C.Y. Zhao and X.L. Tang, Polyhedron, 28, 1419 (2009); doi:10.1016/j.poly.2009.03.017; (c) W.K. Dong, L. Li, C.F. Li, L. Xu and J.G. Duan, Spectrochim. Acta A, 71, 650 (2008); doi:10.1016/j.saa.2008.01.020; (d) W.K. Dong, J.Y. Shi, J.K. Zhong, Y.Q. Tian and J.G. Duan, Chinese J. Inorg. Chem., 24, 10 (2008); (e) W.K. Dong, J.G. Duan, Y.H. Guan, J.Y. Shi and C.Y. Zhao, Inorg. Chim. Acta, 362, 1129 (2009); doi:10.1016/j.ica.2008.05.028; (f) W.K. Dong, S.S. Gong, J.F. Tong, Y.X. Sun and J.C. Wu Chinese J. Inorg. Chem., 26, 1868 (2010); (g) W.K. Dong, Y.X. Sun, C.Y. Zhao, X.Y. Dong and L. Xu, Polyhedron, 29, 2087 (2010); doi:10.1016/j.poly.2010.04.006; (h) W.K. Dong, L.S. Zhang, Y.X. Sun, M.M. Zhao, G. Li and X.Y. Dong, Spectrochim. Acta A, 121, 324 (2014); doi:10.1016/j.saa.2013.10.072; (i) W.K. Dong, Y.X. Sun, X.Y. Dong, S.J. Xing and L. Wang, J. Coord. Chem., 66, 3291 (2013); doi:10.1080/00958972.2013.834426.
- H.E. Smith, Chem. Rev., 83, 359 (1983); doi:10.1021/cr00056a001.
References
D.J. Zhou, Q. Li, C.H. Huang, U. Shigeo, M. Masakazu, L.M. Ying and A.C. Yu, Polyhedron, 16, 1381 (1998); doi:10.1016/S0277-5387(96)00382-8.
M.J. Kharodawala and A.K. Rana, Synth. React. Inorg. Met.-Org. Chem, 33, 1483 (2003); doi:10.1081/SIM-120024324.
S. Akine, T. Taniguchi and T. Nabeshima, Angew. Chem. Int. Ed., 41, 4670 (2002); doi:10.1002/anie.200290011.
M.F. Braña, A. Gradillas, A.G. Ovalles, B. López, N. Acero, F. Llinares and D.M. Mingarro, Bioorg. Med. Chem., 14, 9 (2006); doi:10.1016/j.bmc.2005.09.059.
S. Akine, T. Taniguchi, W. Dong, S. Masubuchi and T. Nabeshima, J. Org. Chem., 70, 1704 (2005); doi:10.1021/jo048030y.
M. Sasaki, K. Manseki, H. Horiuchi, M. Kumagai, M. Sakamoto, H. Sakiyama, Y. Nishida, M. Sakai, Y. Sadaoka, M. Ohba and H. Okawa, J. Chem. Soc., Dalton Trans., 259 (2000); doi:10.1039/a907423f.
S.S. Sun, C.L. Stern, S.T. Nguyen and J.T. Hupp, J. Am. Chem. Soc., 126, 6314 (2004); doi:10.1021/ja037378s.
J.C.G. Bünzli and C. Piguet, Chem. Rev., 102, 1897 (2002); doi:10.1021/cr010299j.
S. Akine, T. Taniguchi and T. Nabeshima, Chem. Lett., 30, 682 (2001); doi:10.1246/cl.2001.682.
S. Akine, W.K. Dong and T. Nabeshima, Inorg. Chem., 45, 4677 (2006); doi:10.1021/ic060055n.
(a) S. Akine, Y. Morita, F. Utsuno and T. Nabeshima, Inorg. Chem., 48, 10670 (2009); doi:10.1021/ic901372k; (b) W.K. Dong, X.N. He, H.B. Yan, Z.W. Lv, X. Chen, C.Y. Zhao and X.L. Tang, Polyhedron, 28, 1419 (2009); doi:10.1016/j.poly.2009.03.017; (c) W.K. Dong, L. Li, C.F. Li, L. Xu and J.G. Duan, Spectrochim. Acta A, 71, 650 (2008); doi:10.1016/j.saa.2008.01.020; (d) W.K. Dong, J.Y. Shi, J.K. Zhong, Y.Q. Tian and J.G. Duan, Chinese J. Inorg. Chem., 24, 10 (2008); (e) W.K. Dong, J.G. Duan, Y.H. Guan, J.Y. Shi and C.Y. Zhao, Inorg. Chim. Acta, 362, 1129 (2009); doi:10.1016/j.ica.2008.05.028; (f) W.K. Dong, S.S. Gong, J.F. Tong, Y.X. Sun and J.C. Wu Chinese J. Inorg. Chem., 26, 1868 (2010); (g) W.K. Dong, Y.X. Sun, C.Y. Zhao, X.Y. Dong and L. Xu, Polyhedron, 29, 2087 (2010); doi:10.1016/j.poly.2010.04.006; (h) W.K. Dong, L.S. Zhang, Y.X. Sun, M.M. Zhao, G. Li and X.Y. Dong, Spectrochim. Acta A, 121, 324 (2014); doi:10.1016/j.saa.2013.10.072; (i) W.K. Dong, Y.X. Sun, X.Y. Dong, S.J. Xing and L. Wang, J. Coord. Chem., 66, 3291 (2013); doi:10.1080/00958972.2013.834426.
H.E. Smith, Chem. Rev., 83, 359 (1983); doi:10.1021/cr00056a001.