The Electrochemical Preparation and Study of Strong Carbon-, Nitrogen-, and Oxygen-Centered Bases

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This project is in the general area of analytical and surface chemistry and in the subfield of organic electrochemistry. The thrust of this experimental program is to investigate the electrochemical preparation of strong Bronsted bases in solution and to study their electrochemical properties and their reactions. Specifically, Professor Hawley and his students will (1) develop electrochemical methods for the preparation of the conjugate bases of weak Bronsted acids; (2) determine the redox potentials of these anions; (3) study the reactions of these anions with electroinactive substrates; (4) determine the regioselectivity of deprotonation of ambident Bronsted acids as well as the kinetics of isomerization of the regioisomers; (5) examine the regioselectivity associated with protonation of the ambident electrogenerated bases; and (6) explore the preparation of electrogenerated bases that give rise to hypercatalytic activity. These studies are important to our knowledge of the thermodynamic properties and reaction kinetics of radical ions and related species that lead to the development and refinement of general theories of electron transfer. Additionally, Professor Hawley's studies should be of importance to the continued development of organic chemistry and in increasing our understanding of many reactions that are extremely useful in the synthesis of new materials.