Electrochemical Analysis of Oxidation of Primary Amines to Ketones with 3,5-Di-Tert-Butyl-1,2Benzoquinone
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Abstract
Electrochemical techniques have been used extensively to study electrode reactions and the coupled chemical-electrochemical reactions. Moreover, the concentration of redox active species in many of the redox reactions can be measured electrochemically, enabling the study of the chemical redox reactions by electrochemical techniques. This area of research in electrochemistry is unexplored and there are only few examples in literature. In this thesis we demonstrated the capability of electrochemical techniques for study of oxidation reaction of amines to ketones by 3,5-di-tert-butyl-1,2-benzoquinone (DTQ). The concentration profiles of quinone and aminocatechol, as the redox active components of reaction, were monitored in the course of reaction by chronoamperometric and voltammetric techniques. The use of microelectrodes, instead of traditional disk electrodes, allowed access to the bulk concentrations of electroactive species while minimizing electrode reactions and the effect of the diffusion layer. The first chapter of this thesis discusses the importance of a class of electroactive compounds known as quinones and their role in some biologically and chemically related redox reactions. Followed by a comparison of the characteristics of microelectrodes versus traditional electrodes as well as interpretation of voltammograms that will appear throughout this work. Chapter two describes fabrication of microelectrodes that were used for this study and the detailed experimental reaction conditions. In chapter three, the oxidation reactions of three amines including: 3-penthylamine, cyclohexylamine, and 1-penthylamine with DTQ were explored and studied by voltammetric and chronoamperometric monitoring of DTQ and aminocatechol. This study provides insight into the intermediate compounds that are formed in the course of reaction, as well as providing a method of determining the rate of reaction of DTQ with a given amine.
Table of Contents
Introduction and Background -- Experimental -- Results and discussion -- Conclusion and outlook