Year of Award

2026

Document Type

Dissertation

Degree Type

Doctor of Philosophy (PhD)

Degree Name

Chemistry

Other Degree Name/Area of Focus

Bioinorganic Chemistry

Department or School/College

Department of Chemistry and Biochemistry

Committee Chair

Orion B. Berryman

Commitee Members

Dong Wang, Bruce E. Bowler, Kent D. Sugden, J. Stephen Lodmell

Keywords

Aliphatic C-H Bond Activation, Catalyst Design, Functionalization, Metal Oxo, Non-Oxo Species, Predictive System

Abstract

Activation of inert carbon-hydrogen (C-H) bonds remains a challenge in synthetic chemistry. High-valent metal-oxo species serve as nature’s oxidants, but their transient nature limits systematic study and subsequent tuning of their reactivity. This dissertation establishes a predictive blueprint for C-H activation using a tunable, redox-active Cobalt(IV) pincer system (LCoIVX2), isolating the topological and electronic variables governing oxidation mechanisms. We discovered that anion topology dictates kinetic distribution. For example, strong axial σ-donors induce a ground-state orbital inversion (d(z2) → d(yz)) that relaxes spatial reactivity demands, and, for some ancillary ligands, a conduit effect drives increased HAT rates by delocalizing the oxidative hole.

Late transition metals reside beyond the theoretical “oxo wall,” precluding stable terminal metal-oxo complexes. Utilizing a non-oxo cobalt system circumvents this structural limitation. Applying our calibrated predictive model to this surrogate system successfully extrapolates the effective basicity and intrinsic reactivity of the elusive M=O moiety. Fortuitously, thermodynamic profiling revealed the reaction solvent acts as a non-innocent participant in high-valent cobalt chemistry, where outer-sphere reorganization penalties impose energetic impedance on reactivity. This slowed reaction speed allowed for the successful kinetic capture of the M=O reaction rate, providing an opportunity to utilize the prediction system produced herein to uncover the thermodynamic properties previously hidden by conventional methods. Further testing of thermodynamic limits with basic anions exposes catalyst turnover capacity and ligand backbone vulnerabilities.

Finally, this work presents the mechanistic picture of high-valent cobalt-mediated C-H bond activation. The decoupling of geometric reorganization from thermodynamic driving force yields a multi-tiered Hierarchy of Orbital Tuning Parameters to guide rational catalyst design.

Available for download on Wednesday, April 28, 2027

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© Copyright 2026 Michael Anthony Kayne