Publication Date

8-1990

Advisor(s) - Committee Chair

Robert Holman, John Reasoner, Curtis Wilkins

Degree Program

Department of Chemistry

Degree Type

Master of Science

Abstract

Radical ions are reactive intermediates that are both radicals and ions (either a radical cation or a radical anion). The intrinsic properties of radical ions are not yet well -characterized. Such knowledge is mechanistically important to the organic chemist.

The specific question that motivates this research is as follows: is it possible to controllably express free radical processes in a radical ion independent of ionic chemistry (and vice versa) and, if so, what factors dictate which type of chemistry is expressed?

Our investigation focused on the chemistry of radical anions of dicyanoalkanes that are formed upon metal reduction. Factors influencing this chemistry such as solvent effects were also studied. This study represents a small segment of a larger study of five functional group classes of molecules, that will ultimately involve a description of the chemistry of radical anions. The goal of the overall project is to attain a generalized view of the chemistry of radical anions of bifunctional organic molecules.

The results obtained suggest that free-radical processes (cyclization and polymerization) can be expressed within radical anions. Furthermore, our results show that free -radical polymerization as opposed to cyclization is the dominant mode of reaction. Such an observation has not been established before for radical anion systems.

The requisite background information regarding what is known about these reactive intermediates to date, and rationalization as to why more information is needed through this, and the work of other scientists, is laid out in the following introduction.

Disciplines

Chemistry | Physical Sciences and Mathematics | Polymer Chemistry

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