Voltammetric Studies on the Reduction Potentials of Perfluoroalkyl Halides and Their Analogous Compounds

Abstract

Photocatalytic single-electron transfer (SET) reactions involving perfluoroalkyl halides play a crucial role in synthetic organic chemistry. However, the electrochemical data for these compounds, which are essential in the discussion of the SET process, are missing. In this study, the electrochemical reduction potentials of perfluoroalkyl halides, alkyl halides, and other analogous compounds were investigated in 0.1 M Bu4NPF6/CH3CN using Ag, Pt, and glassy carbon electrodes. The Ag electrode showed remarkable catalytic properties and a positive reduction peak shift during the reduction reaction; this indicates that the Ag electrode is suitable for estimating the electrochemical potential of the SET process. This study provides a comprehensive dataset for the electrochemical measurements of perfluoroalkyl and alkyl halides, which will help synthetic organic chemists select appropriate reaction systems for these compounds.

Keywords

• perfluoroalkyl halide
• alkyl halide
• linear sweep voltammetry
• fluorine chemistry