Eighteen chlorophenols, containing from one to five chlorine atoms on the benzene ring at various positions, have been studied by cyclic voltammetric methods to evaluate their oxidation-reduction characteristics in an aprotic medium. The compounds were dissolved in dimethylsulfoxide containing 0.10 M tetrabutylammonium perchlorate as the supporting electrolyte and were then both oxidized and reduced on a glassy carbon electrode. The results indicate that phenols oxidize in a one-step process to phenoxium ion which dimerizes to quinone ether. The ether can be reduced back to phenol in a two-step reduction process. The oxidation potential of the chlorophenols varies with the number and the position of the chlorine substitution. It may also have a relationship with the toxicity of the compound. The main purpose of this study is to understand low chlorophenols, classified as environmental pollutants for their toxicity and carcinogenicity, are oxidized by cytochrome P450 in the metabolic activation process in living systems.
Sorrells, Cecil A.; Shaikh, Ali U.; and Samokyszyn, Victor M.
"Oxidation-Reduction Characteristics of Chlorophenols in an Aprotic Medium,"
Journal of the Arkansas Academy of Science: Vol. 56
, Article 26.
Available at: http://scholarworks.uark.edu/jaas/vol56/iss1/26