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Topic

Charge-Tagging Synthetic Methodologies for Mass Spectrometric Analysis of Complex Systems

Department of Chemistry

Date & location

• Monday, August 25, 2025
• 2:00 P.M.
• Elliott Building, Room 226

Examining Committee

Supervisory Committee

• Dr. Scott McIndoe, Department of Chemistry, University of Victoria (Supervisor)
• Dr. Jeremy Wulff, Department of Chemistry, UVic (Member)
• Dr. David Goodlett, Department of Biochemistry and Microbiology, UVic (Outside Member)

External Examiner

• Dr. Jolene Reid, Department of Chemistry, University of British Columbia

Chair of Oral Examination

• Dr. Michel Lefebvre, Department of Physics and Astronomy, UVic

Abstract

The introductory chapter provides a background of the logic and methodology behind the central themes of this thesis. The reader is introduced to the mass spectrometric techniques used, and the design, synthesis, and use of charge-tagged compounds in electrospray ionization mass spectrometric studies is discussed.

Chapter 2 details the synthesis of charge-tagged bis-alkene compounds, and their use as substrates in an investigation of a ruthenium-catalyzed ring-closing metathesis reaction. Through real-time reaction monitoring with pressurized sample infusion, kinetic and dynamic behaviour of reaction byproducts and intermediates is revealed, along with an investigation of catalyst decomposition and the incidence of alkene isomerization.

Chapter 3 presents the synthesis of a new charge-tagged N-heterocyclic carbene ligand for mass spectrometric investigation. This ligand, termed ESIMes, is designed to confer high electrospray response, preserve the steric and electronic environment of the neutral equivalent ligand, and remain compatible with the reaction conditions under which the neutral equivalent is employed.

Chapter 4 moves away from real-time reaction monitoring and instead discusses a challenging problem of chemical analysis. Through using the charge-tagging strategy together with the reactivity of trifluoromethyl aryl diazirines, a tandem insertion and electrospray-tagging process is developed to enable analysis of a class of nonpolar compounds amongst the most difficult to traditionally characterize with mass spectrometry.
Chapter 5 investigates the proficiency of different solvents for mass spectrometry with two model charge-tagged compounds. Through this study, a previously unused and promising candidate for this method of analysis is revealed in trifluorotoluene.