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Simple Descriptors for Modeling the Solubility of Gases, Alcohols, and Halogenated Hydrocarbons in Water

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Simple Descriptors for Modeling the Solubility of Gases, Alcohols, and Halogenated Hydrocarbons in Water Wright State University CORE Scholar Browse all Theses and Dissertations Theses and Dissertations 2007 Simple Descriptors for Modeling the Solubility of Gases, Alcohols, and Halogenated Hydrocarbons in Water Sule Sidigu Wright State University Follow this and additional works at: https://corescholar.libraries.wright.edu/etd_all Part of the Chemistry Commons Repository Citation Sidigu, Sule, "Simple Descriptors for Modeling the Solubility of Gases, Alcohols, and Halogenated Hydrocarbons in Water" (2007). Browse all Theses and Dissertations. 194. https://corescholar.libraries.wright.edu/etd_all/194 This Thesis is brought to you for free and open access by the Theses and Dissertations at CORE Scholar. It has been accepted for inclusion in Browse all Theses and Dissertations by an authorized administrator of CORE Scholar. For more information, please contact [email protected]. SIMPLE DESCRIPTORS FOR MODELING THE SOLUBILITY OF GASES, ALCOHOLS, AND HALOGENATED HYDROCARBONS IN WATER A thesis submitted in partial fulfillment of the requirements for the degree of Master of Science By SULE SIDIGU B.A., Kenyon College, 2003 2007 Wright State University COPYRIGHT BY SULE SIDIGU 2007 WRIGHT STATE UNIVERSITY SCHOOL OF GRADUATE STUDIES September 16, 2007 I HEREBY RECOMMEND THAT THE THESIS PREPARED UNDER MY SUPERVISION BY Sule Sidigu ENTITLED Simple Descriptors for Modeling the Solubility of Gases, Alcohols, and Halogenated Hydrocarbons in Water BE ACCEPTED IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF Master of Science __________________ Rubin Battino, Ph.D. Thesis Director ___________________ Kenneth Turnbull, Ph.D. Department Chair Committee on Final Examination _________________________ Rubin Battino, Ph.D. _________________________ Paul G. Seybold, Ph.D. _________________________ David A. Dolson, Ph.D. _________________________ Joseph F. Thomas, Jr., Ph.D. Dean, School of Graduate Studies ABSTRACT Sidigu, Sule. M.S., Department of Chemistry, Wright State University, 2007. Simple Descriptors for Modeling the Solubility of Gases, Alcohols, and Halogenated Hydrocarbons. The Statmost, QSARIS, Excel, and SAS programs were used to model the solubility of gases, alcohols, and halogenated hydrocarbons in water using simple physical and topological descriptors. The alcohols were well-modeled using measures of the number of carbons, terminal methyls, and steric hindrance about the hydroxyl group. Molecular mass, boiling point, and critical volume or critical pressure were the best descriptors for the halogenated hydrocarbons. Critical pressure was the most applicable single descriptor for the gases. Molecular mass and boiling point also yielded good results for the gases and halogenated hydrocarbons when regressed together. iv TABLE OF CONTENTS Page 1. Simple Descriptors for Modeling the Solubility of Gases, Alcohols, and Halogenated Hydrocarbons in Water……………………………………………...1 History……………………………………………………………………………..1 Solubility Units……………………………………………………………………6 Solubility Data Sources……………………………………………………………8 The Solubility Process…………………………………………………………….9 Modeling Solubility……………………………………………………………….9 Regression Statistics………………………………………………..……………16 Nature and Structure of Water…………………………………………………...18 Importance of Gases, Water, and the Halogenated Hydrocrabons………………22 References…………………………………………………………………..……25 2. Aqueous Solubility of Alcohols at 298.15K Abstract…………………………………………………………………………..30 Introduction…...………………………………………………………………….30 Methods…………………………………………………………………………..31 Results……………………………………………………………………………36 Discussion…..……………………………………………………………………43 Conclusion…………………………………………………………………….…45 References………………………………………………………………..………45 v 3. Aqueous Solubility of Halogenated Hydrocarbons at 298.15K Abstract…………………………………………………………………………..47 Introduction……………………………………………………………………...48 Methods…………………………………………………………………………50 Results…………………………………………………………………………..52 Discussion……………………………………………………………………….60 Conclusion………………………………………………………………………64 Appendix………………………………………………………………………..65 References…..…………………………………………………………………..89 4. Aqueous Solubility of Various Gases at 298.15K Abstract…………………………………………………………………………93 Introduction……………………………………………………………………..94 Methods…………………………………………………………………………97 Results…………………………………………………………………………..101 Discussion………………………………………………………………………108 Conclusion……………………………………………………………………...114 References……………………………………………………………………...115 5. Conclusion Introduction…………………………………………………………………….118 Aqueous Solubility of Alcohols………………………………………………..118 Aqueous Solubility of Halogenated Hydrocarbons………………………...…..119 Aqueous Solubility of Gases……………………………………………….......119 Conclusion……………………………………………………………………...120 vi References…………………………………………………………………...…120 vii LIST OF FIGURES Page Fig. 1.1 H2O molecules transferring from a beaker of pure H2O to one containing CH3OH (aq) in a closed system…………………………………………………………...2 Fig. 1.2 Plot of f1 and f2 vs. x2 for an ideal solution………………………………………3 Fig. 1.3 The behavior of a real gas comparing Henry’s Law and Raoult’s Law………...4 Fig. 1.4 The movement of gas molecules with respect to pressure applied by a piston….5 Fig. 1.5 Hydrogen suppressed chemical graph of butane………………………………..10 Fig. 1.6 Polarizability and dipole moment of H2O………………………………………15 Fig. 1.7 Residuals as shown on a frequency distribution………………………………...18 Fig. 1.8 The three principal vibrational motions of the water molecule…………………21 Fig. 2.1 The hydrogen-suppressed graph of 2-methyl-1-propanol………………………36 Fig. 4.1 Types of intermolecular forces………………………………………………….94 Fig. 4.2 NaCl as an example of an ion-ion interaction…………………………………..95 Fig. 4.3 London forces between two ethane molecules………………………………….96 viii LIST OF TABLES Page Table 1.1 Bond lengths and angles of heavy water (D2O) as compared to H2O………………………………………………………………………………21 Table 1.2 Common Propellants…………………………………………………..24 Table 2.1 Solubilities of Alcohols in Water as Reported by Yalkowsky and Valvani and Amidon et al, as Ordered by Increasing Difference………………..32 Table 2.2 Alcohol Solubilities in Molal and Molar Units From the Dataset of Yalkowsky and Valvani, as Ordered by Increasing Solubilities…………………34 Table 2.3 Statistics for the Parameters in Equation 1 (NC, TM, CA)…………...37 Table 2.4 Experimental and Calculated Molar Solubilities (Eqn.1: NC, TM, CA) in Water………………………………………………………………………….39 Table 2.5 Experimental and Calculated Molar Solubilities (Eqn.3: NC) in Water…………………………………………………………………….………41 Table 2.6 Alcohols Not Well Accounted for by the Present Models……………43 Table 3.1 Experimental Descriptors Used in This Study………………………..50 Table 3.2 Topological Descriptors Used in This Study…………………………51 Table 3.3 Molecules Not Used for Eqns.1-4…………………………………….53 Table 3.4 Molecules Not Used for Eqn.5………………………………………..54 Table 3.5 Regressions Based on Topological Descriptors……………………….56 Table 3.6 Principal Component Analysis of the Experimental Descriptors……..57 Table 3.7 Experimental Descriptors Principal Component Analysis Factor Loadings………………………………………………………………………....58 Table 3.8 Principal Component Analysis of the Topological Descriptors………58 ix Table 3.9 Topological Descriptors Principal Component Analysis Factor Loadings…………………………………………………………………………59 Table 3.10 Pearson Correlation Matrix of the Physical Descriptors…………….60 Table 3.11 Outliers in Regerssions 1-5………………………………………….63 Table A3.1 Descriptors Used in This Study as Arranged by Decreasing lnx2…..66 Table A3.2 Regression Statistics for MM, Tb, & Vc: Graph 1, Eqn.1…………...73 Table A3.3 Regression Statistics for MM, Tb, & Pc: Graph 2, Eqn.2……………76 Table A3.4 Regression Statistics for MM, Tc, & Pc: Graph 3, Eqn.3……………79 Table A3.5 Regression Statistics for MM, Tc, & Vc: Graph 4, Eqn.4…………...83 Table A3.6 Regression Statistics for MM & Tc: Graph 5, Eqn.5………………..86 Table 4.1 Chemically Nonreactive Gases Used in This Study as Ordered by MM…..…………………………………………………………………………..98 Table 4.2 Chemically Reactive Gases Used in This Study as Ordered by MM…99 Table 4.3 Permanent and Noble Gases Used in This Study as Ordered by MM...99 Table 4.4 Halogenated Hydrocarbons Used in This Study as Ordered by MM..100 Table 4.5 Additional Regressions of the Nonreactive Gases…………………...101 Table 4.6 Additional Regressions of the Permanent and Noble Gases…………103 Table 4.7 Additional Regresions of the Halogenated Hydrocarbons…………..104 Table 4.8 Chemically Nonreactive Gases Pearson Correlation Table………….105 Table 4.9 Chemically Reactive Gases Pearson Correlation Table……………..106 Table 4.10 Permanent and Noble Gases Pearson Correlation Table…………...107 Table 4.11 Halogenated Hydrocarbons Pearson Correlation Table…………….108 Table 4.12 Outliers in Regressions 1-5………..………………………………..110 x LIST OF GRAPHS Pages Graph 2.1 Experimental and Calculated Alcohol Solubilities (Eqn.1 NC, TM, CA) in Water…………………………………………………………………………………......38 Graph 2.2 Experimental and Calculated Alcohol Solubilities (Eqn.3 NC) in Water…...40 Graph 2.3 Experimental and Calculated Alcohol Solubilities (Eqn.2 NC, TM, CA) in Water…………………………………………………………………………………….42 Graph 2.4 Experimental and Calculated (Eqn.4 NC) Alcohol Solubilities in Water……42 Graph 3.1. lnx2exp vs lnx2calc (Eqn.1 MM, Tb, & Vc)……….………………………….73 Graph 3.2. lnx2exp vs lnx2calc (Eqn.2 MM, Tb, & Pc)……….………………………….76 Graph 3.3. lnx2exp vs lnx2calc (Eqn.3 MM, Tc, & Pc)………..........................................79 Graph 3.4 lnx2exp vs lnx2calc (Eqn.3 MM, Tc, & Vc)……..............................................83 Graph 3.5. lnx2exp vs lnx2calc (Eqn.3 MM & Tc)………………………………………86 2 3 Graph 4.1
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