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ACID-BASE REACTIONS in DIFFERENT SOLID-STATE FORMS Haichen Nie Purdue University

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ACID-BASE REACTIONS in DIFFERENT SOLID-STATE FORMS Haichen Nie Purdue University Purdue University Purdue e-Pubs Open Access Dissertations Theses and Dissertations January 2016 ACID-BASE REACTIONS IN DIFFERENT SOLID-STATE FORMS Haichen Nie Purdue University Follow this and additional works at: https://docs.lib.purdue.edu/open_access_dissertations Recommended Citation Nie, Haichen, "ACID-BASE REACTIONS IN DIFFERENT SOLID-STATE FORMS" (2016). Open Access Dissertations. 1295. https://docs.lib.purdue.edu/open_access_dissertations/1295 This document has been made available through Purdue e-Pubs, a service of the Purdue University Libraries. Please contact [email protected] for additional information. Graduate School Form 30 Updated PURDUE UNIVERSITY GRADUATE SCHOOL Thesis/Dissertation Acceptance This is to certify that the thesis/dissertation prepared By Haichen Nie Entitled ACID-BASE REACTIONS IN DIFFERENT SOLID-STATE FORMS For the degree of Doctor of Philosophy Is approved by the final examining committee: Stephen R. Byrn Patrick J. Marsac Chair Lynne S. Taylor Rodolfo Pinal Gregory T. Knipp To the best of my knowledge and as understood by the student in the Thesis/Dissertation Agreement, Publication Delay, and Certification Disclaimer (Graduate School Form 32), this thesis/dissertation adheres to the provisions of Purdue University’s “Policy of Integrity in Research” and the use of copyright material. Approved by Major Professor(s): Stephen R. Byrn Approved by: Rodolfo Pinal 8/26/2016 Head of the Departmental Graduate Program Date i ACID-BASE REACTIONS IN DIFFERENT SOLID-STATE FORMS A Dissertation Submitted to the Faculty of Purdue University by Haichen Nie In Partial Fulfillment of the Requirements for the Degree of Doctor of Philosophy i December 2016 Purdue University West Lafayette, Indiana ii ACKNOWLEDGEMENTS First and foremost, I would like to express my deepest appreciation and gratitude to my advisor Professor Stephen R. Byrn and my co-advisor Professor Lynne S. Taylor for their continuous support, generous help, and excellent mentorship throughout my graduate studies. Many thanks are also due to the members of my advisory committee, Dr. Rodolfo Pinal, Dr. Gregory T. Knipp, and Dr. Patrick J. Marsac for their precious suggestions on my research projects and warm encouragement for my career. Dr. Wei Xu and Mr. Christopher T. John are acknowledged for their valuable advice on salt stability projects. Special thanks are extended to Dr. Huaping Mo, Professor Tonglei Li, and Dr. Mingtao Zhang for their active input and kind assistance. The Industrial and Physical Pharmacy Department of Purdue and Pre-formulation Department of Merck & Co., Inc. are acknowledged for providing me an excellent platform to facilitate this work. I would also like to thank my friends and family for their warmth and companionship. Finally, my sincerest appreciation goes to my amazing parents and Zhiyi Cui for their love, encouragement, understanding, and constant support. ii iii TABLE OF CONTENTS Page LIST OF TABLES ........................................................................................................... viii LIST OF FIGURES ........................................................................................................... xi ABSTRACT ....................................................................................................................... xx CHAPTER 1. THEORY AND BACKGROUND ............................................................ 1 1.1 Theories of acids and bases ....................................................................................... 1 1.1.1 Lewis theory of acid and base.......................................................................... 1 1.1.2 Brønsted-Lowry theory of acid and base ......................................................... 2 1.1.3 Activity and equilibrium constant of water dissociation ................................. 2 1.1.4 Equilibrium constant of acid and base in aqueous solution ............................. 4 1.1.5 Relationship between chemical structure and acidity ...................................... 5 1.2 Fundamentals of ionic equilibria ............................................................................... 6 1.2.1 Ionic equilibria of monoprotic electrolytes...................................................... 6 1.2.2 Ionic equilibria of polyportic electrolytes........................................................ 9 1.2.3 Ionic equilibria of amphoteric electrolytes .................................................... 10 1.3 Solubility behaviors of acids, bases and salts.......................................................... 12 1.3.1 Fundamentals of pH-solubility profiles, Ksp and pHmax ................................. 12 1.3.2 Effects of intrinsic solubility, pKa and Ksp on pHmax ................................. 17 iii 1.3.3 Effects of counterion and common-ion effects .............................................. 19 1.4 Hygroscopicity of pharmaceutical solids ................................................................ 22 1.4.1 Water-solid interactions ................................................................................. 24 1.4.2 Effects of moisture on physicochemical stability and physical mechanical properties ................................................................................................................... 30 1.5 Acid-Base Reactions ............................................................................................... 31 iv 1.5.1 Theory of acid-base reactions ........................................................................ 31 1.5.2 Salt formation and disproportionation ........................................................... 32 1.5.3 Solid state acid-base reactions ....................................................................... 34 1.6 Research Overview.................................................................................................. 36 CHAPTER 2. INVESTIGATING THE INTERACTION PATTERN AND STRUCTURAL ELEMENTS OF A DRUG-POLYMER COMPLEX AT THE MOLECULAR LEVEL .................................................................................................... 38 2.1 Abstract: .................................................................................................................. 38 2.2 Keywords................................................................................................................. 39 2.3 Introduction ............................................................................................................. 40 2.4 Experimental ........................................................................................................... 43 2.4.1 Chemicals....................................................................................................... 43 2.4.2 Preparation of solid dispersion ...................................................................... 43 2.4.3 Powder X-Ray diffraction (PXRD) ............................................................... 44 2.4.4 Ultraviolet-Visible spectroscopy ................................................................... 44 2.4.5 Solution NMR ................................................................................................ 44 2.4.6 Computational methods ................................................................................. 45 2.5 Results ..................................................................................................................... 46 2.5.1 Powder X-Ray diffraction.............................................................................. 46 2.5.2 Ultraviolet Visible Spectroscopy ................................................................... 46 iv 2.5.3 Solution NMR ................................................................................................ 47 2.6 Discussion ............................................................................................................... 50 2.7 Conclusion ............................................................................................................... 56 CHAPTER 3. SOLID-STATE SPECTROSCOPIC INVESTIGATION OF MOLECULAR INTERACTIONS BETWEEN CLOFAZIMINE AND HYPROMELLOSE PHTHALATE IN AMORPHOUS SOLID DISPERSIONS............ 65 3.1 Abstract ................................................................................................................... 65 3.2 Keywords................................................................................................................. 66 3.3 Introduction ............................................................................................................. 67 3.4 Experimental ........................................................................................................... 70 v 3.4.1 Materials ........................................................................................................ 70 3.4.2 Preparation of solid dispersion ...................................................................... 70 3.4.3 Powder X-Ray diffraction (PXRD) ............................................................... 71 3.4.4 Solid-State Ultraviolet-Visible (UV/Vis) spectroscopy ................................ 71 3.4.5 Infrared (IR) spectroscopy ............................................................................. 72 3.4.6 Solid-state NMR spectroscopy (ssNMR) ...................................................... 72 3.4.7 Computational methods ................................................................................. 73 3.5 Results and Discussion ...........................................................................................
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