Kipp Brian H, Faraj Chadi, Li Guoliang, Njus David
Department of Biological Sciences, Wayne State University, Detroit, MI 48202, USA.
Bioelectrochemistry. 2004 Aug;64(1):7-13. doi: 10.1016/j.bioelechem.2003.12.010.
In cyclic voltammetry studies at pH 8, imidazole facilitates oxidation of organic compounds that normally lose hydrogen atoms. High concentrations of imidazole shift the oxidizing wave of ascorbic acid, 2,3-dimethoxy-5-methyl-1,4-hydroquinone, and the vitamin E analogue Trolox toward lower potentials. By contrast, imidazole has no effect on the cyclic voltammogram of methyl viologen, which undergoes electron rather than hydrogen-atom transfer. The effect of imidazole is observed at pH 8.0 but only to a lesser extent at pH 5.5 indicating that imidazole must be unprotonated to facilitate oxidation. Digital simulation shows that these results are consistent with a mechanism in which imidazole acts as a proton acceptor permitting concerted proton/electron transfer by the organic reductant.
