Oxidation potential of benzylferrocenes and related compounds:: effects of the ortho-methoxy substituent in the phenyl group

被引:10
作者
Asahara, M [1 ]
Natsume, S [1 ]
Kurihara, H [1 ]
Yamaguchi, T [1 ]
Erabi, T [1 ]
Wada, M [1 ]
机构
[1] Tottori Univ, Fac Engn, Dept Mat Sci, Tottori 6800945, Japan
关键词
benzylferrocenes; ferrocenyl derivatives; o-methoxyphenyl; oxidation potential; X-ray crystal structure;
D O I
10.1016/S0022-328X(00)00075-9
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Oxidation potentials of some ferrocenyl derivatives of type Fc-CH Phi OH, Fc-C Phi Phi'OH, FcCH(2)Phi, Fc-CH Phi Phi' [Fc = Fe(eta(5-)C(5)H(5))(eta(5)-C5H4); Phi, Phi' = 2,4,6-(MeO)(3)C6H2, 2,6-(MeO)(2). C6H3, 2,5-(MeO)(2). C6H3, 2,4-(MeO)(2). C6H3, 2-MeOC6N4, 4-MeOC6H4, C6H5] were measured in acetonitrile. All of them exhibited a reversible one-electron oxidation-reduction wave based on the ferrocene-ferrocenium redox couple with a wide range of shift. Compounds having ortho-methoxy groups showed lower redox potentials than those of compounds having para-methoxy groups. The X-ray crystal structure of Fc-CH Phi(2)(n),it showed that the ortho-methoxy oxygens was situated very close to the central carbon, and there is a possibility that one of the oxygen lone-pairs interacts with the antibonding orbital of C-Fc sigma-bond. Some other possibilities are also discussed. (C) 2000 Elsevier Science S.A. All rights reserved.
引用
收藏
页码:246 / 252
页数:7
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