Electrocatalytic-Frustrated Lewis pair hydrogen oxidation using novel benzothiazolium salts

Woodhouse, Sarah (2020) Electrocatalytic-Frustrated Lewis pair hydrogen oxidation using novel benzothiazolium salts. Doctoral thesis, University of East Anglia.

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Abstract

The aim this project was to synthesise benzothiazolines/benzothiazolium salts with a variety of functional groups on the C2 aryl ring, in order to fine tune the hydridicity of the C2-H for electrocatalytic hydrogen oxidation. The synthesis was successful and a variety of different compounds were made and the functionality did affect the hydridicity of the C2-H (Chapter 4). However, problems arose with the frustrated Lewis pair activation of the cycle with adduct formation. This is discussed further in Chapter 5.
In chapter 1, several different ways of hydrogen production are discussed, from steam reformation to hydrogenases. Also included is the utilisation of hydrogen, from hydrogen fuel cells to hydrogen cleavage/activation, for use in chemical transformations, using frustrated Lewis pairs.
Chapter 2 shows the successful synthesis of a variety of different molecules, from di-thiol linked, substituted imines to benzothiazolium salts to N-methyl-2-(aryl)benzothiazolines.
Chapter 3 includes the results and discussion of the syntheses, discussing the unexpected synthesis of di-thiol linked substituted imines, and the successful synthesis of a variety of novel N-methyl-2-(aryl)benzothiazolines.
In chapter 4, the electrochemical analysis of a variety of synthesised N-methyl-2- (aryl)benzothiazolines is discussed. Analysis of the variable scan rate (VSR) cyclic voltammetry produced Randles-Sevcik plots in order to determine the relationship between peak current and √scan rate. For electrochemically reversible electron transfer processes that involve freely diffusing redox species, this relationship is linear.
Chapter 5 introduces the hydride transfer experiments for the N-methyl-2-(4- nitrophenyl)benzothiazolium salt, which indicated successful transfer, although a slow transformation. Investigations into alternative boranes were undertaken and the results are discussed.

Item Type: Thesis (Doctoral)
Faculty \ School: Faculty of Science > School of Chemistry
Depositing User: Nicola Veasy
Date Deposited: 30 Mar 2022 12:03
Last Modified: 30 Mar 2022 12:03
URI: https://ueaeprints.uea.ac.uk/id/eprint/84351
DOI:

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