287410-91-7Relevant academic research and scientific papers
Oxidation potential of benzylferrocenes and related compounds: Effects of the ortho-methoxy substituent in the phenyl group
Asahara, Masahiro,Natsume, Satoko,Kurihara, Hideaki,Yamaguchi, Takuya,Erabi, Tatsuo,Wada, Masanori
, p. 246 - 252 (2000)
Oxidation potentials of some ferrocenyl derivatives of type Fc-CHΦOH, Fc-CΦΦ′OH, Fc-CH2Φ, Fc-CHΦΦ′ [Fc=Fe(η5-C5H5)(η5-C 5H4); Φ, Φ′=2,4,6-(MeO)3C6H2, 2,6-(MeO)2·C6H3, 2,5-(MeO)2·C6H3, 2,4-(MeO)2·C6H3, 2-MeOC6H4, 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-CHΦ2a showed that the ortho-methoxy oxygens were 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 σ-bond. Some other possibilities are also discussed.
