College Honors Program

In-Solution Detection of Chalcogen Bonding

Date of Creation

7-2023

Document Type

Thesis

Department

Chemistry

First Advisor

Brian R. Linton

Abstract

Sulfur is a ubiquitous presence in pharmaceutical and biochemical compounds but is often ignored in discussions regarding the contributions of non-covalent forces to the confirmational preferences of relevant molecules. With that being said, the molecular framework investigated in this thesis demonstrates an unusual reliance on two particularly elusive intramolecular forces that involve sulfur: sulfur-as-acceptor hydrogen bonding and sulfur-oxygen chalcogen bonding. By following the 1H NMR downfield shift of various iterations of this amide structure under changing environmental conditions (e.g., solvent composition, concentration), significant differences in sensitivity were correlated with subtle molecular changes. Analysis of these differences provided evidence for the existence of both intramolecular six-membered S···H-N hydrogen bonding and intramolecular five-membered S···O chalcogen bonding within our investigative framework. Each of these forces demonstrated dependence on the identity of the phenyl substituent. Furthermore, a Lewis acid effect was observed to result from chalcogen bonding. These findings are particularly relevant to biochemists and medicinal chemists interested in the conformational preferences of sulfur-containing proteins and pharmaceuticals.

Comments

Reader: Bianca R. Sculimbrene

This document is currently not available here.

Share

COinS