First Advisor

David R. Stuart

Date of Award

Spring 5-24-2024

Document Type

Thesis

Language

English

Subjects

iodine compounds, diaryliodonium salts, zwitterions, binding study

DOI

10.15760/honors.1565

Abstract

Diaryliodonium salts can be used as effective aryl-transfer agents in reactions to form novel molecules with diverse applications including pharmaceuticals and agrochemicals without using harsh reaction conditions and transition metal reagents. In recent years, interest in the applications of the Lewis acidity of iodonium ion catalysts has increased. Despite this, the quantification of the Lewis acidities of diaryliodonium salts are scarce. Even rarer, there has not been much study into the Lewis acidities of zwitterionic diaryliodonium salts. For zwitterions, there is no counter anion that would come into consideration in regard to its Lewis acidity. To expand the understanding of the Lewis acidity of diaryliodonium salts, this work sought to quantify the binding of a variety of zwitterionic diaryliodonium salts. Multiple titrations of zwitterionic diaryliodonium salts and DABCO resulted in different 1H NMR spectra for which the aromatic peaks with the greatest shift were recorded. Nonlinear regression was performed to afford a Kb value and a plot of Δδ vs. guest concentration. Of all the zwitterionic species, only the imidazole mesityl iodonium zwitterion could be dissolved at an appropriate concentration to do a binding study. Due to complications regarding pipetting and shimming of NMR spectra, the resultant binding constants could not reliably be determined. Further binding studies of zwitterionic species and their respective imidazole aryl iodonium acetates could allow quantification of binding constants in relation to the presence of a zwitterion.

Comments

An undergraduate honors thesis submitted in partial fulfillment of the requirements for the degree of Bachelor of Science in University Honors and Biology and Science.

Persistent Identifier

https://archives.pdx.edu/ds/psu/42167

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