Synthesis, Crystal Structure and Redox Property of a Copper(II) Complex Based on 1,1-Bis(1H-benzoimidazol-2-ylmethyl)cyclohexane
潘荣楷;李国璧;刘生桂;杨桂珍;周晓平;陈晓荧
a (School of Chemistry and Chemical Engineering,Lingnan Normal University, Zhanjiang 524048, China)
b (Industrial Technology Research Institute, Lingnan Normal University, Zhanjiang 524048 ,China)
Synthesis, Crystal Structure and Redox Property of a Copper(II) Complex Based on 1,1-Bis(1H-benzoimidazol-2-ylmethyl)cyclohexane
PAN Rong-Kai;LI Guo-Bi;LIU Sheng-Gui;YANG Gui-Zhen;ZHOU Xiao-Ping;CHEN Xiao-Ying
a (School of Chemistry and Chemical Engineering,Lingnan Normal University, Zhanjiang 524048, China)
b (Industrial Technology Research Institute, Lingnan Normal University, Zhanjiang 524048 ,China)
A novel mononuclear copper(II) complex [Cu(bbmc)Cl2]•DMF, where bbmc is 1,1-bis(1H-benzoimidazol-2-ylmethyl)cyclohexane, was synthesized and characterized by X-ray single-crystal structure analysis. The complex crystallizes in triclinic, space group P with a = 9.1088(5), b = 11.0075(4), c = 14.2326(6) Å, α = 97.188(3), β = 96.394(4), γ = 111.430(4)°, V = 1298.73(10) Å3, Z = 2, Dc = 1.409 g/cm3, μ(MoKα) = 1.074 mm-1, F(000) = 572, S = 1.078, R = 0.0381 and wR = 0.0876 for 5593 observed reflections with I > 2σ(I). The central Cu(II) ion adopts a distorted tetrahedral geometry coordinated by two nitrogen atoms of the ligand and two chloride ions. The complex showed its thermal decomposition temperature up to 226 ℃ and exhibited an irreversible one-electron transfer process involving CuII/CuI couple.
A novel mononuclear copper(II) complex [Cu(bbmc)Cl2]•DMF, where bbmc is 1,1-bis(1H-benzoimidazol-2-ylmethyl)cyclohexane, was synthesized and characterized by X-ray single-crystal structure analysis. The complex crystallizes in triclinic, space group P with a = 9.1088(5), b = 11.0075(4), c = 14.2326(6) Å, α = 97.188(3), β = 96.394(4), γ = 111.430(4)°, V = 1298.73(10) Å3, Z = 2, Dc = 1.409 g/cm3, μ(MoKα) = 1.074 mm-1, F(000) = 572, S = 1.078, R = 0.0381 and wR = 0.0876 for 5593 observed reflections with I > 2σ(I). The central Cu(II) ion adopts a distorted tetrahedral geometry coordinated by two nitrogen atoms of the ligand and two chloride ions. The complex showed its thermal decomposition temperature up to 226 ℃ and exhibited an irreversible one-electron transfer process involving CuII/CuI couple.
Financially supported from National Natural Science Foundation of China (No. 21403191), Natural Science Foundation of Guangdong Province (Nos. 2014A030307010 and 2015A0303010406), Special funds for public welfare research and capacity building in Guangdong Province (No. 2015A010105031), Zhanjiang Science Technology Project (No. 2013B01054) and Lingnan Normal University Science Research Foundation (Nos. L1301 and LZL1504)
通讯作者:
lsgui@sohu.com
E-mail: lsgui@sohu.com
引用本文:
潘荣楷;李国璧;刘生桂;杨桂珍;周晓平;陈晓荧. Synthesis, Crystal Structure and Redox Property of a Copper(II) Complex Based on 1,1-Bis(1H-benzoimidazol-2-ylmethyl)cyclohexane[J]. 结构化学, 2016, 35(3): 348-354.
PAN Rong-Kai;LI Guo-Bi;LIU Sheng-Gui;YANG Gui-Zhen;ZHOU Xiao-Ping;CHEN Xiao-Ying. Synthesis, Crystal Structure and Redox Property of a Copper(II) Complex Based on 1,1-Bis(1H-benzoimidazol-2-ylmethyl)cyclohexane. CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2016, 35(3): 348-354.
REFERENCES
(1) Chassaing, C.; Berger, M.; Heckeroth, A.; Ilg, T.; Jaeger, M.; Kern, C.; Schmid, K.; Uphoff, M. Highly water-soluble prodrugs of anthelmintic benzimidazole carbamates: synthesis, pharmacodynamics and pharmacokinetics. J. Med. Chem. 2008, 51, 1111-1114.
(2) Halafi-Nezhad, A. K.; Soltani Rad, M. N.; Mohabatkar, H.; Asrari, Z.; Hemmateenejad, B. Design, synthesis, antibacterial and QSAR studies of benzimidazole and imidazole chloroaryloxyalkyl derivatives. Bioorg. Med. Chem. 2005, 13, 1931-1938.
(3) Liu, S.; Nelson, C. A.; Xiao, L.; Lu, L.; Seth, P. P.; Davis, D. R.; Hagedorn, C. H. Measuring antiviral activity of benzimidazole molecules that alter IRES RNA structure with an infectious hepatitis C virus chimera expressing Renilla luciferase. Antiviral Res. 2011, 89, 5463.
(4) Sączewski, F.; Dziemidowicz-Borys, E.; Bednarski, P. J. Synthesis, crystal structure and biological activities of copper(II) complexes with chelating bidentate 2-substituted benzimidazole ligands. J. Inorg. Biochem. 2006, 100, 1389-1398.
(5) Wu, H. L.; Zhang, Y. H.; Zhang, J. W.; Yang, Z. H.; Chen, C. Y.; Peng, H. P.; Wang, F. Synthesis, crystal structures, electrochemical studies, and antioxidant activities of manganese(II) and copper(II) complexes of bis(N-allylbenzimidazol-2-ylmethyl)aniline. Transit. Met. Chem. 2015, 40, 145152.
(6) Lin, J. J.; Meng, F. Y.; Li, X. H. Synthesis, crystal structure and in vitro anticancer studies of 1,2-bis-benzimidazole-phenyl copper(II) complex. Chin J. Struct. Chem. 2015, 34, 41-48.
(7) Mann, J.; Baron, A.; Opoku-Boahen, Y.; Johansson, E.; Parkinson, G.; Kelland, L. R.; Neidle, S. A new class of symmetric bis-benzimidazole-based DNA minor groove-binding agents showing antitumor activity. J. Med. Chem. 2001, 44, 138-144.
(8) Su, W. Y.; Li, G. B.; Pan, R. K.; Tang, F. Q.; Zhong, L.; Liu, S. G. Synthesis, crystal structure and luminescent property of cadmium complex based on 2-(2-(1H-benzo[d]imidazol-2-yl)benzyl)-1H-benzo[d]-imidazole. Chin. J. Struct. Chem. 2015, 33, 909-914.
(9) Wu, Q. T,; Wu, L. B.; Li, G. B.; Liu, S. G.; Pan, R. K.; Su, W. Y.; Huang, Q. W. Synthesis, crystal structure and luminescent property of a dinuclear cadmium complex based on 1,2,3,4-tetra(1H-benzo[d]imidazol-2-yl)butane. Chin. J. Struct. Chem. 2015, 34, 260-266.
(10) Che, Z. J.; Wang, S. X.; Liu, S, G.; Li, G. B.; Wu, Q. T.; Lin, C. Y.; Kong, L. L.; Wang, S. Synthesis, structure, photoluminescence and antitumour activity of zinc complex based on 2-(2-(1H-benzo-[d]imidazol-2-yl)benzyl)-1H-benzo-[d]imidazole. Spectrochim. Acta A 2015, 135, 878882.
(11) Pan, R. K.; Liu, S. G.; Wang, S. X.; Li, G. B.; Su, W. Y.; Huang, Q. W.; He, Y. M. Synthesis, crystal structure, luminescent property and anti-esophageal tumor activity of dinuclear zinc complex based on meso-1,2,3,4-tetra(1H-benzo[d]imidazol-2-yl)butane. Z. Anorg. Allg. Chem. 2015, 641, 627630.
(12) Li, G. B.; Wang, S. X.; Su, W. Y.; Pan, R. K.; Liu, K. D.; Liu, S. G. Synthesis, crystal structure, and antitumour activities of cobalt(II) complex based on 2,6-bis(1-phenylbenzimidazol-2-yl)pyridine. Russ. J. Coord. Chem. 2014, 40, 764767.
(13) Bhat, S. S.; Kumbhar, A. A.; Heptullah, H.; Khan, A. A.; Gobre, V. V.; Gejji, S. P.; Puranik, V. G. Synthesis, electronic structure, DNA and protein binding, DNA cleavage, and anticancer activity of fluorophore-labeled copper(II) complexes. Inorg. Chem. 2011, 50, 545-558.
(14) Sunita, M.; Padmaja, M.; Anupama, B.; Gyana Kumari, C. Synthesis, characterization, DNA binding and cleavage studies of mixed-ligand Cu(II) complexes of 2,6-bis(benzimidazol-2-yl)pyridine. J. Fluoresc. 2012, 22, 1003-1012.
(15) Sheldrick, G. M. SHELXS-97, Program for the Solution of Crystal Structures. University of Göttingen, Germany 1997.
(16) Sheldrick, G. M. SHELXL-97, Program for the Refinement of Crystal Structures from Diffraction Data. University of Göttingen, Germany 1997.
(17) Stibrany, R. T. Structures of bis(1-ethylbenzimidazol-2-yl)alkyl copper(II) dichlorides: an unusual cocrystallization. J. Chem. Crystallogr. 2009, 39, 719722
(18) Deng, Z. P.; Huo, L. H.; Zhao, H.; Gao, S. A co-crystal strategy to tune the supramolecular patterns and luminescent properties: ten well-designed salts assembled by arenedisulfonic acid with diverse diamines. Cryst. Growth. Des. 2012, 12, 33423355.