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Investigation of the Electrochemical Reduction of Benzophenone in Aprotic Solvents Using the Method of Cyclic Voltammetry

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Abstract

The reduction of benzophenone (Bzph) in 3-pentanone (PEN), acetone (ACE), N,N-dimethylacetamide (DMA), N,N-dimethylformamide (DMF), tetrahydrofuran (THF), acetonitrile (ACN) and dimethyl sulfoxide (DMSO) with n-tetrabutylammonium hexafluorophosphate (TBAPF6) as background electrolyte was studied using the technique of cyclic voltammetry at the temperature of 263.15 K. The half-wave potentials (E 1/2) were extracted. The reduction of Bzph occurs in two successive one-electron steps to produce first the free radical anion Bzph− and then the dianion Bzph2−. The results indicated that the radical anion Bzph− is reoxidized to Bzph in all investigated solvent media whereas the dianion Bzph2− is reoxidized to Bzph− only in THF. The heterogeneous electron-transfer rate constants (k s ) were evaluated by employing the electrochemical rate equation proposed by Nicholson. The rate of electron transfer for the Bzph/Bzph− couple was found to be relatively slow in all investigated solvent media. Consequently, the electron-transfer processes can be recognized as quasi-reversible. The diffusion coefficients (D) of Bzph in the investigated solvent media have been calculated using the modified Randles-Sevcik equation. The effect of the physical and chemical properties of the solvent medium on the electrochemical behavior of Bzph has been examined.

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  1. Institut für Chemie, Humboldt-Universität zu Berlin, Brook-Taylor-Straße 2, D-12489, Berlin, Germany

    Nikos G. Tsierkezos

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Tsierkezos, N.G. Investigation of the Electrochemical Reduction of Benzophenone in Aprotic Solvents Using the Method of Cyclic Voltammetry. J Solution Chem 36, 1301–1310 (2007). https://doi.org/10.1007/s10953-007-9188-4

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  • DOI: https://doi.org/10.1007/s10953-007-9188-4

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