This grant in Organic and Macromolecular Chemistry provides support for the research of Dr. Vernon Parker, Utah State University. The work consists of a systematic study of the reactions and reactivity of organic anion radicals, dianions, cation radicals, and dications. Such reactive organic species are important intermediates in a wide variety of organic reactions and an understanding of their behavior has important practical signficance, particularly for electrode processes and polymerization reactions. Using quantitative electrochemical methods, a number of reaction types will be studied including (i) reactions of cationic intermediates with nucleophiles, both neutral and anionic, (ii) proton transfer reactions of cation radicals and dications derived from methylarenes, and (iii) protonation reactions of anion radicals and dianions. Specific issues which will be addressed are (i) the intrinsic reactivity of ion radicals as compared to the corresponding doubly charged ions and (ii) the factors contributing to the rates of proton transfer to and from carbon of super acidic (basic) ion radicals and doubly charged ions. These will provide fundamental new knowledge of importance to reactive intermediate chemistry.