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UNIVERSITY of CALIFORNIA, MERCED Deuterium Kinetic UNIVERSITY OF CALIFORNIA, MERCED Deuterium Kinetic Isotope Effects as Mechanistic Probes for Synthetically Useful Cyclic Hydrogen Transfers A dissertation submitted in partial satisfaction of the requirements for the degree Doctor of Philosophy in Chemistry and Chemical Biology by Xiao Li Committee in Charge: Professor Benjamin J. Stokes, Chair Professor Andy LiWang Professor Matthew P. Meyer, Advisor Professor Jason Hein © Xiao Li 2016 All Rights Reserved The Dissertation of Xiao Li is approved, and it is acceptable in quality and form for publication on microfilm and electronically: Professor Andy LiWang Professor Matthew P. Meyer Professor Jason Hein Professor Benjamin J. Stokes (Chair) University of California, Merced 2016 iii DEDICATION I dedicate this dissertation to the ambition and resilience I have developed in the past of my life, without which I could not have completed this work. I could not gain the strength of my mind and body without my parents, my husband Ding Li, my other family members, friends and mentors who supported me along the way. I would like to express my deepest gratitude to my parents who always encourage me to live up to my full potential. I deeply thank my husband Ding Li whose love and generosity to me is one of the most important sources of my passion to the world. iv TABLE OF CONTENTS LIST OF ABBREVIATION ............................................................................................. vii LIST OF FIGURES ......................................................................................................... viii LIST OF TABLES .............................................................................................................. x ACKNOWLEDGEMENTS ............................................................................................... xi CURRICULUM VITA ..................................................................................................... xii ABSTRACT ..................................................................................................................... xiii Chapter 1. Introduction and Background ...................................................................... 1 1.1. Importance of Reaction Mechanisms ............................................................................................. 1 1.2. Hydrogen Transfer Reactions: Importance, Limitations in Current Understanding and the Scope of this Dissertation ...................................................................................................................................... 1 1.3. General Introduction to Kinetic Isotope Effect .............................................................................. 3 1.3.1. Primary Kinetic Isotope Effect .............................................................................................. 3 1.3.2. Secondary Kinetic Isotope Effect .......................................................................................... 5 1.4. Quantum Mechanical Effects Upon Hydrogen Transfer ................................................................ 6 1.4.1. The Nature and Physical Principles of Quantum Tunneling ................................................. 6 1.4.2. The Phenomenological Manifestations of the Tunnel Effect ................................................ 8 1.5. Traditional and New Experimental Methods for KIE Measurement ........................................... 10 1.6. Computational Methods for Calculating Kinetic Isotope Effect .................................................. 15 1.6.1. Bigeleisen Equation ............................................................................................................ 15 1.6.2. POLYRATE ........................................................................................................................ 16 Chapter 2. Mechanistic Study of the Chugaev Elimination ........................................ 19 2.1 Mechanistic Background and Synthetic Utility of the Chugaev Elimination .............................. 19 2.2. Methods ....................................................................................................................................... 19 2.1.2. Intermolecular KIE Measurement ....................................................................................... 20 2.3. Results and Discussion ................................................................................................................ 22 2.3.1. Temperature Dependence of 2H KIEs ................................................................................. 22 2.3.2. Effects of Driving Force upon 2H KIEs .............................................................................. 26 2.4. Conclusion ................................................................................................................................... 28 2.5. Experimental Section ................................................................................................................... 29 2.5.1. Material Preparation ............................................................................................................ 29 2.5.2. Procedure for KIE Measurement ......................................................................................... 33 v Chapter 3. Mechanistic Study of the Cope Elimination .............................................. 35 3.1. Mechanistic Background and Synthetic Utility of the Cope Elimination .......................................... 35 3.2. Methods ............................................................................................................................................. 35 3.2.1. Intramolecular KIE measurement ............................................................................................... 35 3.2.2. LFER studies .............................................................................................................................. 36 3.3. Results and Discussion....................................................................................................................... 37 3.3.1. The Temperature Dependence of the Intramolecular KIE for Three Different Substituents. ..... 37 3.3.2. The LFER of the Cope Elimination. ........................................................................................... 39 3.4. Conclusion ......................................................................................................................................... 40 3.5. Experimental Section ......................................................................................................................... 41 3.5.1. Material preparation.................................................................................................................... 41 3.5.2. The Procedure for KIE measurements ........................................................................................ 44 13 3.5.3. T1 Measurement for C NMR in the LFER study ..................................................................... 45 Chapter 4. Mechanistic Study of Ru-Catalyzed C-H functionalization..................... 47 4.1. Synthetic Utility and Mechanistic Background of the Du Bois C–H Amination ......................... 47 4.2. Method ......................................................................................................................................... 48 4.2.1. Intramolecular KIE.............................................................................................................. 48 4.2.2. Intermolecular KIE.............................................................................................................. 49 4.3. Results and Discussion ................................................................................................................ 50 4.3.1. Temperature Dependence of Intramolecular 2H KIEs ......................................................... 50 4.3.2. The Effect of Magnetic Field on the Intramolecular KIE of the Ru-catalyzed C-H Amination 51 4.3. Experimental Section ................................................................................................................... 52 4.3.1. Material Preparation ............................................................................................................ 52 4.3.2. Temperature Controlled Ru-catalyzed C-H Amination and KIE Measurement .................. 55 SUMMARY ...................................................................................................................... 56 REFERENCE .................................................................................................................... 57 NMR SPECTRA ............................................................................................................... 58 vi LIST OF ABBREVIATION KIE kinetic isotope effect TS transition state TST transition state theory ZPE zero-point energy RGM the rule of the geometric mean CVT canonical variational transition state theory SCT small curvature tunneling NMR nuclear magnetic resonance SMD solvation model based on density LFER linear free energy relationship THF tetrahydrofuran DMSO dimethyl sulfoxide RBF round bottom flask TLC think layer chromatography FID free induction decay S/N signal to noise ratio vii LIST OF FIGURES Figure 1. Reactions studied in this dissertation.. ................................................................ 2 Figure 2. Diagrams illustrating the origin primary KIE. .................................................... 3 Figure 3. Potential energy
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