Insights into the transport of aqueous quaternary ammonium cations: A combined experimental and computational study

Journal of Physical Chemistry B

Volumn 118, Issue 5, 2014, Pages 1363-1372

  Sarode, Himanshu N ^a   Lindberg, Gerrick E ^b   Yang, Yuan ^a   Felberg, Lisa E ^b   Voth, Gregory A ^b   Herring, Andrew M ^a  

^a Department of Metallurgical and Materials Engineering   (United States)

^b UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM HYDROXIDE SOLUTION; BENZYLTRIMETHYLAMMONIUM; BENZYLTRIMETHYLAMMONIUM HYDROXIDE; COMPUTATIONAL APPROACH; COMPUTATIONAL STUDIES; DIFFUSION MEASUREMENTS; MOLECULAR DYNAMICS SIMULATIONS; SELF-DIFFUSION COEFFICIENTS;

CARBON DIOXIDE; DIFFUSION; EXPERIMENTS; IONIC CONDUCTIVITY; MOLECULAR DYNAMICS; NEGATIVE IONS;

POSITIVE IONS;

ANION; BENZYLTRIMETHYLAMMONIUM; CARBON; CARBON DIOXIDE; CARBONIC ACID DERIVATIVE; CATION; HYDROXIDE; HYDROXIDE ION; QUATERNARY AMMONIUM DERIVATIVE; TETRAMETHYLAMMONIUM; WATER;

ARTICLE; CHEMISTRY; ELECTRIC CONDUCTIVITY; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ANIONS; CARBON DIOXIDE; CARBON ISOTOPES; CARBONATES; CATIONS; ELECTRIC CONDUCTIVITY; HYDROXIDES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR DYNAMICS SIMULATION; QUATERNARY AMMONIUM COMPOUNDS; WATER;

EID: 84893818971     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp4085662     Document Type: Article

References (61)

1. MacKinnon, R.; Yellen, G. Mutations Affecting TEA Blockade and Ion Permeation in Voltage-Activated K+ Channels Science 1990, 250, 276-279
2. Babiaczyk, W. I.; Bonella, S.; Guidoni, L.; Ciccotti, G. Hydration Structure of the Quaternary Ammonium Cations J. Phys. Chem. B 2010, 114, 15018-15028
3. Lan, C. J.; Lee, C. Y.; Chin, T. S. Tetra-Alkyl Ammonium Hydroxides as Inhibitors of Zn Dendrite in Zn-Based Secondary Batteries Electrochim. Acta 2007, 52, 5407-5416
4. Couture, G.; Alaaeddine, A.; Boschet, F.; Ameduri, B. Polymeric Materials as Anion-Exchange Membranes for Alkaline Fuel Cells Prog. Polym. Sci. 2011, 36, 1521-1557
5. Merle, G.; Wessling, M.; Nijmeijer, K. Anion Exchange Membranes for Alkaline Fuel Cells: A Review J. Membr. Sci. 2011, 377, 1-35
6. Kawai, K.; Kaneko, K.; Yonezawa, T. Hydrophilic Quaternary Ammonium Type Ionic Liquids. Systematic Study of the Relationship among Molecular Structures, Osmotic Pressures, and Water-Solubility Langmuir 2011, 27, 7353-7356
7. Samakande, A.; Hartmann, P. C.; Sanderson, R. D. Synthesis and Characterization of New Cationic Quaternary Ammonium Polymerizable Surfactants J. Colloid Interface Sci. 2006, 296, 316-323
8. Starks, C. M. Heterogeneous Reactions Involving Anion Transfer by Quaternary Ammonium and Phosphonium Salts J. Am. Chem. Soc. 1971, 93, 195-199
9. Leng, Y. J.; Chen, G.; Mendoza, A. J.; Tighe, T. B.; Hickner, M. A.; Wang, C. Y. Solid-State Water Electrolysis with an Alkaline Membrane J. Am. Chem. Soc. 2012, 134, 9054-9057
10. Faraj, M.; Boccia, M.; Miller, H.; Martini, F.; Borsacchi, S.; Geppi, M.; Pucci, A. New LDPE Based Anion-Exchange Membranes for Alkaline Solid Polymeric Electrolyte Water Electrolysis Int. J. Hydrogen Energy 2012, 37, 14992-15002
11. Brand, H. V.; Curtiss, L. A.; Iton, L. E.; Trouw, F. R.; Brun, T. O. Theoretical and Inelastic Neutron-Scattering Studies of Tetraethylammonium Cation as a Molecular-Sieve Template J. Phys. Chem. 1994, 98, 1293-1301
12. Coletta, F.; Ferrarini, A.; Gottardi, F.; Nordio, P. L. NMR Relaxation in Long-Chain Quaternary Ammonium-Ions-The Role of Torsional Flexibility Chem. Phys. 1995, 192, 19-24
13. Wait, E.; Powell, H. M. The Crystal and Molecular Structure of Tetraethylammonium Iodide J. Chem. Soc. 1958, 1872-1875
14. Nagano, Y.; Mizuno, H.; Sakiyama, M.; Fujiwara, T.; Kondo, Y. Hydration Enthalpy of Tetra-Normal-Butylammonium Ion J. Phys. Chem. 1991, 95, 2536-2540
15. Paddison, S. J.; Kreuer, K.-D.; Maier, J. About the Choice of the Protogenic Group in Polymer Electrolyte Membranes: Ab Initio Modelling of Sulfonic Acid, Phosphonic Acid, and Imidazole Functionalized Alkanes Phys. Chem. Chem. Phys. 2006, 8, 4530-4542
16. Kreuer, K.-D.; Paddison, S. J.; Spohr, E.; Schuster, M. Transport in Proton Conductors for Fuel-Cell Applications: Simulations, Elementary Reactions, and Phenomenology Chem. Rev. 2004, 104, 4637-4678
17. Paddison, S. J.; R. Pratt, L.; Zawodzinski, T.; Reagor, D. W. Molecular Modeling of Trifluoromethanesulfonic Acid for Solvation Theory Fluid Phase Equilib. 1998, 150-151, 235-243
18. 2O: Calorimetric and Near-Infrared Spectroscopic Study J. Phys. Chem. B 2012, 117, 877-883
19. Finney, J. L.; Soper, A. K. Solvent Structure and Perturbations in Solutions of Chemical and Biological Importance Chem. Soc. Rev. 1994, 23, 1-10
20. Stangret, J.; Gampe, T. Hydration Sphere of Tetrabutylammonium Cation. FTIR Studies of HDO Spectra J. Phys. Chem. B 1999, 103, 3778-3783
21. Turner, J. Z.; Soper, A. K.; Finney, J. L. Ionic versus Apolar Behavior of the Tetramethylammonium Ion in Water J. Chem. Phys. 1995, 102, 5438-5443
22. Turner, J.; Soper, A. K. The Effect of Apolar Solutes on Water-Structure-Alcohols and Tetraalkylammonium Ions J. Chem. Phys. 1994, 101, 6116-6125
23. Varcoe, J. R.; Slade, R. C. T. Prospects for Alkaline Anion-Exchange Membranes in Low Temperature Fuel Cells Fuel Cells 2005, 5, 187-200
24. Hibbs, M. R.; Fujimoto, C. H.; Cornelius, C. J. Synthesis and Characterization of Poly(phenylene)-Based Anion Exchange Membranes for Alkaline Fuel Cells Macromolecules 2009, 42, 8316-8321
25. Zhang, Y. M.; Fang, J.; Wu, Y. B.; Xu, H. K.; Chi, X. J.; Li, W.; Yang, Y. X.; Yan, G.; Zhuang, Y. Z. Novel Fluoropolymer Anion Exchange Membranes for Alkaline Direct Methanol Fuel Cells J. Colloid Interface Sci. 2012, 381, 59-66
26. Gu, S.; Cai, R.; Luo, T.; Chen, Z. W.; Sun, M. W.; Liu, Y.; He, G. H.; Yan, Y. S. A Soluble and Highly Conductive Ionomer for High-Performance Hydroxide Exchange Membrane Fuel Cells Angew. Chem., Int. Ed. 2009, 48, 6499-6502
27. Jung, M. S. J.; Arges, C. G.; Ramani, V. A Perfluorinated Anion Exchange Membrane with a 1,4-Dimethylpiperazinium Cation J. Mater. Chem. 2011, 21, 6158-6160
28. Gu, S.; Cai, R.; Yan, Y. Self-Crosslinking for Dimensionally Stable and Solvent-Resistant Quaternary Phosphonium Based Hydroxide Exchange Membranes Chem. Commun. 2011, 47, 2856-2858
29. Arges, C. G.; Parrondo, J.; Johnson, G.; Nadhan, A.; Ramani, V. Assessing the Influence of Different Cation Chemistries on Ionic Conductivity and Alkaline Stability of Anion Exchange Membranes J. Mater. Chem. 2012, 22, 3733-3744
30. Tsai, T.-H.; Maes, A. M.; Vandiver, M. A.; Versek, C.; Seifert, S.; Tuominen, M.; Liberatore, M. W.; Herring, A. M.; Coughlin, E. B. Synthesis and Structure-Conductivity Relationship of Polystyrene-Block-Poly(vinyl benzyl trimethylammonium) for Alkaline Anion Exchange Membrane Fuel Cells J. Polym. Sci., Part B: Polym. Phys. 2013, 51, 1751-1760
31. Yan, J.; Hickner, M. A. Anion Exchange Membranes by Bromination of Benzylmethyl-Containing Poly(sulfone)s Macromolecules 2010, 43, 2349-2356
32. Koga, Y. Solution Thermodynamics and its Application to Aqueous Solutions: A Differential Approach, 1 st ed.; Elsevier Science: Amsterdam, The Netherlands, 2007.
33. Long, H.; Kim, K.; Pivovar, B. S. Hydroxide Degradation Pathways for Substituted Trimethylammonium Cations: A DFT Study J. Phys. Chem. C 2012, 116, 9419-9426
34. Chempath, S.; Einsla, B. R.; Pratt, L. R.; Macomber, C. S.; Boncella, J. M.; Rau, J. A.; Pivovar, B. S. Mechanism of Tetraalkylammonium Headgroup Degradation in Alkaline Fuel Cell Membranes J. Phys. Chem. C 2008, 112, 3179-3182
35. Janarthanan, R.; Horan, J. L.; Caire, B. R.; Ziegler, Z. C.; Yang, Y.; Zuo, X.; Liberatore, M. W.; Hibbs, M. R.; Herring, A. M. Understanding Anion Transport in an Aminated Trimethyl Polyphenylene with High Anionic Conductivity J. Polym. Sci., Part B: Polym. Phys. 2013, 51, 1743-1750
36. Luzhkov, V. B.; Osterberg, F.; Acharya, P.; Chattopadhyaya, J.; Aqvist, J. Computational and NMR Study of Quaternary Ammonium Ion Conformations in Solution Phys. Chem. Chem. Phys. 2002, 4, 4640-4647
37. Ramanathan, P. S.; Krishnan, C. V.; Friedman, H. Models Having the Thermodynamic Properties of Aqueous Solutions of Tetraalkylammonium Halides J. Solution Chem. 1972, 1, 237-262
38. Streng, W. H.; Wen, W.-Y. Calculation of Gurney Parameters for Aqueous Tetraalkylammonium Halides Based on Friedman's Cosphere-Overlap Model J. Solution Chem. 1974, 3, 866-880
39. Schmidt, B. M.; Carlton Brown, L.; Williams, D. Chemical Shifts of N14 in the NMR Spectra of Ammonia and Related Compounds J. Mol. Spectrosc. 1958, 2, 539-550
40. Schipper, F. J. M.; Kassapidou, K.; Leyte, J. C. Polyelectrolyte Effects on Counterion Self-Diffusion J. Phys.: Condens. Matter 1996, 8, 9301-9308
41. Volkov, V. I.; Popkov, Y. M.; Timashev, S. F.; Bessarabov, D. G.; Sanderson, R. D.; Twardowski, Z. Self-Diffusion of Water and Fluorine Ions in Anion-Exchange Polymeric Materials (Membranes and Resin) as Determined by Pulsed-Field Gradient Nuclear Magnetic Resonance Spectroscopy J. Membr. Sci. 2000, 180, 1-13
42. Sodaye, S.; Suresh, G.; Pandey, A. K.; Goswami, A. Determination and Theoretical Evaluation of Selectivity Coefficients of Monovalent Anions in Anion-Exchange Polymer Inclusion Membrane J. Membr. Sci. 2007, 295, 108-113
43. Guijarro, D.; Martinez, P. J.; Najera, C.; Yus, M. Benzyllithium from Methylated Benzylamine and Its Ammonium Salt via Naphthalene-Catalyzed Carbon-Nitrogen Bond Reductive Cleavage Arkivoc 2004, 5-13
44. Pratt, K. W.; Koch, W. F.; Wu, Y. C.; Berezansky, P. A. Molality-Based Primary Standards of Electrolytic Conductivity-(IUPAC Technical Report) Pure Appl. Chem. 2001, 73, 1783-1793
45. Stejskal, E. O.; Tanner, J. E. Spin Diffusion Measurements: Spin Echoes in the Presence of a Time-Dependent Field Gradient J. Chem. Phys. 1965, 42, 288-292
46. Wang, J.; Wolf, R. M.; Caldwell, J. W.; Kollman, P. A.; Case, D. A. Development and Testing of a General Amber Force Field J. Comput. Chem. 2004, 25, 1157-1174
47. Wang, J. M.; Wang, W.; Kollman, P. A.; Case, D. A. Automatic Atom Type and Bond Type Perception in Molecular Mechanical Calculations J. Mol. Graphics Modell. 2006, 25, 247-260
48. Wang, J. M.; Wolf, R. M.; Caldwell, J. W.; Kollman, P. A.; Case, D. A. Development and Testing of a General Amber Force Field J. Comput. Chem. 2004, 25, 1157-1174
49. Wu, Y. J.; Tepper, H. L.; Voth, G. A. Flexible Simple Point-Charge Water Model with Improved Liquid-State Properties J. Chem. Phys. 2006, 124, 024503
50. Jensen, K. P.; Jorgensen, W. L. Halide, Ammonium, and Alkali Metal Ion Parameters for Modeling Aqueous Solutions J. Chem. Theory Comput. 2006, 2, 1499-1509
51. Joung, I. S.; Cheatham, T. E. Determination of Alkali and Halide Monovalent Ion Parameters for Use in Explicitly Solvated Biomolecular Simulations J. Phys. Chem. B 2008, 112, 9020-9041
52. Case, D. A.; Cheatham, T. E.; Darden, T.; Gohlke, H.; Luo, R.; Merz, K. M.; Onufriev, A.; Simmerling, C.; Wang, B.; Woods, R. J. The Amber Biomolecular Simulation Programs J. Comput. Chem. 2005, 26, 1668-1688
53. Impey, R. W.; Madden, P. A.; McDonald, I. R. Hydration and Mobility of Ions in Solution J. Phys. Chem. 1983, 87, 5071-5083
54. Borucka, A. Z.; Bockris, J. O. M.; Kitchener, J. A. Test of the Applicability of the Nernst-Einstein Equation to Self-Diffusion and Conduction of Ions in Molten Sodium Chloride J. Chem. Phys. 1956, 24, 1282-1282
55. Lee, S. H.; Rasaiah, J. C. Proton Transfer and the Mobilities of the H+ and OH- Ions from Studies of a Dissociating Model for Water J. Chem. Phys. 2011, 135, 124505-124510
56. Light, T. S.; Licht, S.; Bevilacqua, A. C.; Morash, K. R. The Fundamental Conductivity and Resistivity of Water Electrochem. Solid-State Lett. 2005, 8, E16-E19
57. Hamann, C. H.; Andrew, H.; Vielstich, W. Electrochemistry; John Wiley & Sons: New York, 1998.
58. Edson, J. B.; Macomber, C. S.; Pivovar, B. S.; Boncella, J. M. Hydroxide Based Decomposition Pathways of Alkyltrimethylammonium Cations J. Membr. Sci. 2012, 399-400, 49-59
59. Macomber, C. S.; Boncella, J. M.; Pivovar, B. S.; Rau, J. A. Decomposition Pathways of an Alkaline Fuel Cell Membrane Material Component via Evolved Gas Analysis J. Therm. Anal. Calorim. 2008, 93, 225-229
60. Schuster, M.; Rager, T.; Noda, A.; Kreuer, K. D.; Maier, J. About the Choice of the Protogenic Group in PEM Separator Materials for Intermediate Temperature, Low Humidity Operation: A Critical Comparison of Sulfonic Acid, Phosphonic Acid and Imidazole Functionalized Model Compounds Fuel Cells 2005, 5, 355-365
61. Haynes, W. M. CRC Handbook of Chemistry and Physics, 93 rd ed.; Taylor & Francis: London, 2012.