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First Line of Title SYNTHESIS OF TRISPYRAZOLYLBORATE-SUPPORTED NICKEL COMPLEXES FOR SMALL MOLECULE ACTIVATION by Ann M. Ploskonka A thesis submitted to the Faculty of the University of Delaware in partial fulfillment of the requirements for the degree of Master of Science in Chemistry and Biochemistry Summer 2015 © 2015 Ann M. Ploskonka All Rights Reserved ProQuest Number: 1602343 All rights reserved INFORMATION TO ALL USERS The quality of this reproduction is dependent upon the quality of the copy submitted. In the unlikely event that the author did not send a complete manuscript and there are missing pages, these will be noted. Also, if material had to be removed, a note will indicate the deletion. ProQuest 1602343 Published by ProQuest LLC (2015). Copyright of the Dissertation is held by the Author. All rights reserved. This work is protected against unauthorized copying under Title 17, United States Code Microform Edition © ProQuest LLC. ProQuest LLC. 789 East Eisenhower Parkway P.O. Box 1346 Ann Arbor, MI 48106 - 1346 SYNTHESIS OF TRISPYRAZOLYLBORATE-SUPPORTED NICKEL COMPLEXES FOR SMALL MOLECULE ACTIVATION by Ann M. Ploskonka Approved: __________________________________________________________ Charles G. Riordan, Ph.D. Professor in charge of thesis on behalf of the Advisory Committee Approved: __________________________________________________________ Murray Johnston, Ph.D. Chair of the Department of Chemistry and Biochemistry Approved: __________________________________________________________ George H. Watson, Ph.D. Dean of the College of Arts and Sciences Approved: __________________________________________________________ James G. Richards, Ph.D. Vice Provost for Graduate and Professional Education ACKNOWLEDGMENTS There are many people who have played a significant role in my education and to whom I owe thanks. First, I would like to thank Dr. Charles G. Riordan for all of his support and guidance over the past three years. You have been an incredible mentor who not only fostered my love of chemistry but always had my best interest at heart. I will be forever grateful for having the opportunity to learn from you how to not just be a better chemist but how to be a great leader as well. I would also like to thank my committee members, Dr. Joseph Fox, Dr. Nora S. Radu, and Dr. Klaus Theopold for their guidance throughout this project and their career advice. I am deeply indebted to my co-workers with whom I have had the privilege to work: Lauren Cordeiro, William Green, Jill Harland, Bryan Klebon, Maxwell Martin, Jessica Wallick, and Peng Wang. I have learned a great deal from each of you on both a personal and professional level. The success of this work would not have been possible without your support. In my time here I have learned how important it is to have an excellent staff and would like to thank the following for their support: Steve Bai (NMR specialist), Susan Cheadle (administrative assistant), Jim Cleaver (instrument specialist), John Famiglietti (Sr. electronics specialist), Sue James (administrative assistant), Doug Nixon (master glass technologist), and Glenn Yap (X-ray crystallographer). I would also like to thank Elizabeth Onderko and Prof. Michael Green of Penn State University for their assistance with the EPR data collection and analysis included in this work. iii I would also like to thank my family for supporting me along every step of this journey. To my mother, Barbara, who has taught me that the most important things aren’t often learned from books. You have and will always be my biggest advocate, best friend, and hero. To my father, Joe, who has been there for me at my best and at my worst and who has helped with all of the countless little things. Thank you for your unconditional love and support. To my brother and sister, David and Rachel, who taught me faith, perseverance, and strength of character by their words and example. Special thanks is owed to my Fidos for Freedom, Inc. family as well for their continued support. I would not be where I am today without my wonderful service dog, Nala, whom they lovingly trained. Finally, I want to offer a very special thank you to all of the people that I have encountered during my time at University of Delaware who have offered a kind word and a warm welcome. You truly make the University of Delaware a wonderful place to work and learn and I am grateful to have been a part of it. iv TABLE OF CONTENTS LIST OF TABLES ...................................................................................................... viii LIST OF FIGURES ....................................................................................................... ix ABSTRACT ................................................................................................................ xvi Chapter 1 INTRODUCTION .............................................................................................. 1 1.1 Bioinorganic Nickel Chemistry ................................................................. 1 1.1.1 Nickel dioxygen chemistry ............................................................ 1 1.1.2 Nickel sulfur and nickel selenium chemistry ................................ 3 1.2 Synthetic Analogues .................................................................................. 6 1.2.1 Nickel dioxygen complexes .......................................................... 6 1.2.2 Nickel sulfur and nickel selenium complexes ............................. 10 1.3 Summary .................................................................................................. 13 2 EXPERIMENTAL ........................................................................................... 14 2.1 Physical Methods ..................................................................................... 14 2.1.1 Nuclear Magnetic Resonance Spectroscopy ............................... 14 2.1.2 Infrared Spectroscopy .................................................................. 14 2.1.3 Mass Spectroscopy ...................................................................... 15 2.1.4 Electronic Absorption Spectroscopy ........................................... 15 2.1.5 Electron Paramagnetic Resonance Spectroscopy ........................ 16 2.1.6 X-Ray Diffraction ........................................................................ 16 2.1.7 Gas Chromatography ................................................................... 17 2.1.8 Combustion Analyses .................................................................. 17 2.2 Experimental ............................................................................................ 17 Ph,Me 2.2.1 Synthesis of [Tp ]NiI ............................................................. 18 Ph,Me 2.2.2 Synthesis of [Tp ]Ni(PPh3) .................................................... 19 2.2.3 Synthesis of [TpPh,Me]Ni(CO) ...................................................... 19 v Ph,Me 2.2.4 Synthesis of [Tp ]Ni(O2) ....................................................... 20 Ph,Me 2.3 Reaction of [Tp ]Ni(O2) with stoichiometric PR3 (R = Me, Et, Cy, Ph) ........................................................................................................... 20 Ph,Me 2.4 Reaction of [Tp ]Ni(O2) with 9, 10-dihydroanthracene .................... 21 Ph,Me 2.5 Reaction of [Tp ]Ni(O2) with 1,4-cyclohexadiene ............................ 22 Ph,Me 2.6 Reaction of [Tp ]Ni(O2) with styrene ................................................ 23 Ph,Me 2.7 Reaction of [Tp ]Ni(O2) with cyclohexene ....................................... 23 Ph,Me 2.8 Aldehyde deformylation using [Tp ]Ni(O2) ...................................... 24 Ph,Me 2.9 Synthesis of [Tp ]Ni(COOH) ............................................................ 24 2.10 Synthesis of ........................................................ 25 Ph,Me 2.11 Synthesis of [Tp ]Ni(SH)................................................................... 26 Ph,Me 2.12 Synthesis of [Tp ]Ni(SCPh3) ............................................................. 26 Ph,Me 2.13 Synthesis of [Tp ]Ni(SePh) ............................................................... 27 Ph,Me 2.14 Synthesis of ([Tp ]Ni)2(μ-Se) ............................................................ 27 2.15 Reaction of with CO ........................................... 28 2.16 Reaction of with PR3 (R = Me, Et) ..................... 28 2.17 Reaction of with O2 ............................................ 29 Fc,Me 2.18 Synthesis of [Tp ]NiCl ....................................................................... 29 Fc,Me 2.19 Synthesis of [Tp ]NiBr ...................................................................... 30 Fc,Me 2.20 Synthesis of [Tp ]NiI ......................................................................... 30 Ind,Me 2.21 Synthesis of [Tp ]NiCl ...................................................................... 31 Ind,Me 2.22 Synthesis of [Tp ]NiI ........................................................................ 31 Ind,Me 2.23 Synthesis of [Tp ]NiBr ...................................................................... 32 Ph,Me 3 SYNTHESIS AND REACTIVITY OF [Tp ]Ni(O2) .................................. 45 Ph,Me 3.1 Synthesis of [Tp ]Ni(O2) ................................................................... 45 Ph,Me 3.2 Thermal Stability and Decomposition Products of [Tp ]Ni(O2) ....... 50 Ph,Me 3.3 Reactivity of [Tp ]Ni(O2) .................................................................. 55 Ph,Me 3.3.1 Reactivity of [Tp ]Ni(O2)
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