Structural influences on the electrochemistry of 1,1′-di(hydroxyalkyl) ferrocenes. Structure of [Fe{η5-C5H4-CH(OH)-(CH2)3OH}2]

被引:9
作者
Claus, Ron [1 ]
Lewtak, Jan P. [1 ]
Muller, Theunis J. [1 ]
Swarts, Jannie C. [1 ]
机构
[1] Univ Orange Free State, Dept Chem, ZA-9300 Bloemfontein, South Africa
关键词
Ferrocene; Alcohol; Dialcohol; Cyclic voltammetry; CONTAINING BETA-DIKETONES; CROSS-COUPLING REACTIONS; ANTINEOPLASTIC ACTIVITY; CONVENIENT SYNTHESIS; CONTAINING ALCOHOLS; CYCLIC VOLTAMMETRY; DERIVATIVES; RUTHENOCENE; COMPLEXES; SERIES;
D O I
10.1016/j.jorganchem.2013.05.006
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A series of 1,1'-di (hydroxyalkyl) ferrocenes, [Fc'{(CH2)(n)OH}(2)], with n = 1 (1), 2 (2), 3 (3) and 4 (4) and Fc' = Fe (eta(5)-C5H4)(2), was synthesized. The electrochemistry of the di(hydroxyalkyl) ferrocenes was studied by cyclic voltammetry in CH2Cl2/0.1 M [(NBu4)-Bu-n][PF6] utilizing a glassy carbon working electrode. The ferrocenyl group showed reversible electrochemistry with the formal reduction potential, E-0', inversely proportional to alkyl chain length and approximately 59 mV smaller than those of the corresponding mono (hydroxyalkyl) ferrocenes derivatives [Fc(CH2)(m)OH] with m = 1 (1m), 2 (2m), 3 (3m), and 4 (4m) and Fc = Fe(eta(5)-C5H5)(eta(5)-C5H4-). The tetraalcohol [Fc'{CH(OH) (CH2)(3)OH}(2)], 5, possessing four OH functionalities, two in the terminal positions and two more, one on each of the two alpha-C relative to the ferrocenyl (Fc' for dialcohols or Fc for monosubstituted derivatives) group, was isolated as a side product during the synthesis of 4. The formal reduction potential of 5 was E-0' = -24 mV vs. FcH/FcH(+) and closely approached E-0' of [FcCH(OH)CH3] (E-0' = -11 mV), [Fc'{CH(OH)CH3}(2)] (-21 mV) and 1 (0.00 mV vs. FcH/FcH(+)). The single crystal X-ray structure of the tetraalcohol 5 (Z = 8, orthorhombic, space group Pbca) was also solved. (C) 2013 Elsevier B. V. All rights reserved.
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页码:61 / 69
页数:9
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