On the origin of proton mobility suppression in aqueous solutions of amphiphiles

Journal of Physical Chemistry B

Volumn 117, Issue 49, 2013, Pages 15426-15435

  Xu, Jianqing ^a   Yamashita, Takefumi ^b   Agmon, Noam ^c   Voth, Gregory A ^a  

^a UNIVERSITY OF CHICAGO   (United States)

^b UNIVERSITY OF TOKYO   (Japan)

^c HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROPHOBIC EFFECT; MEAN SQUARED DISPLACEMENT; POWER LAW EXPONENT; PROTON DIFFUSION; PROTON TRANSPORT; REACTIVE MOLECULAR DYNAMICS; VALENCE BOND MODELS; WATER CONCENTRATIONS;

FUNCTIONAL GROUPS; MOLECULAR DYNAMICS; UREA;

PROTONS;

1,1,3,3-TETRAMETHYLUREA; METHYLUREA; PROTON; TETRAMETHYLUREA; WATER;

ARTICLE; CHEMICAL PHENOMENA; CHEMISTRY; MOLECULAR DYNAMICS; SOLUTION AND SOLUBILITY;

HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; METHYLUREA COMPOUNDS; MOLECULAR DYNAMICS SIMULATION; PROTONS; SOLUTIONS; WATER;

EID: 84890479095     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp4051726     Document Type: Article

References (88)

1. Bell, R. P. The Proton in Chemistry; Cornell University Press: Ithaca, NY, 1959.
2. Kreuer, K.-D. Proton Conductivity: Materials and Applications Chem. Mater. 1996, 8, 610-641
3. 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
4. DeCoursey, T. E. Voltage-Gated Proton Channels and Other Proton Transfer Pathways Physiol. Rev. 2004, 84, 1479-1479
5. Wraight, C. A. Chance and Design-Proton Transfer in Water, Channels and Bioenergetic Proteins Biochim. Biophys. Acta 2006, 1757, 886-912
6. Voth, G. A. Computer Simulation of Proton Solvation and Transport in Aqueous and Biomolecular Systems Acc. Chem. Res. 2006, 39, 143-150
7. Cukierman, S. Et tu, Grotthuss! and Other Unfinished Stories Biochim. Biophys. Acta 2006, 1757, 876-885
8. Marx, D. Proton Transfer 200 Years after von Grotthuss: Insights from Ab Initio Simulations ChemPhysChem 2006, 7, 1848-1870
9. Swanson, J. M. J.; Maupin, C. M.; Chen, H. N.; Petersen, M. K.; Xu, J. C.; Wu, Y. J.; Voth, G. A. Proton Solvation and Transport in Aqueous and Biomolecular Systems: Insights from Computer Simulations J. Phys. Chem. B 2007, 111, 4300-4314
10. Knight, C.; Voth, G. A. The Curious Case of the Hydrated Proton Acc. Chem. Res. 2011, 45, 101-109
11. Marx, D.; Chandra, A.; Tuckerman, M. E. Aqueous Basic Solutions: Hydroxide Solvation, Structural Diffusion, and Comparison to the Hydrated Proton Chem. Rev. 2010, 110, 2174-2216
12. Jorn, R.; Savage, J.; Voth, G. A. Proton Conduction in Exchange Membranes across Multiple Length Scales Acc. Chem. Res. 2012, 45, 2002-2010
13. de Grotthuss, C. J. T. Sur la décomposition de l'eau et des corps qu'elle tient en dissolution à l'aide de l'électricité galvanique Ann. Chim. 1806, LVIII, 54-74
14. Eigen, M. Proton Transfer, Acid-Base Catalysis, and Enzymatic Hydrolysis. Part I: Elementary Processes Angew. Chem., Int. Ed. 1964, 3, 1-19
15. Zundel, G. Easily Polarizable Hydrogen Bonds-Their Interactions with the Environment-IR Continuum and Anomalous Large Proton Conductivity. In The Hydrogen Bond, Recent Developments in Theory and Experiments; Schuster, P.; Zundel, G.; Sandorfy, C., Eds.; North-Holland: Amsterdam, The Netherlands, 1976; pp 687-766.
16. Agmon, N. The Grotthuss Mechanism Chem. Phys. Lett. 1995, 244, 456-462
17. Tuckerman, M. E.; Marx, D.; Klein, M. L.; Parrinello, M. On the Quantum Nature of the Shared Proton in Hydrogen Bonds Science 1997, 275, 817-820
18. Marx, D.; Tuckerman, M. E.; Hutter, J.; Parrinello, M. The Nature of the Hydrated Excess Proton in Water Nature 1999, 397, 601-604
19. Ohmine, I.; Saito, S. Water Dynamics: Fluctuation, Relaxation, and Chemical Reactions in Hydrogen Bond Network Rearrangement Acc. Chem. Res. 1999, 32, 741-749
20. Day, T. J. F.; Schmitt, U. W.; Voth, G. A. The Mechanism of Hydrated Proton Transport in Water J. Am. Chem. Soc. 2000, 122, 12027-12028
21. Lapid, H.; Agmon, N.; Petersen, M. K.; Voth, G. A. A Bond-Order Analysis of the Mechanism for Hydrated Proton Mobility in Liquid Water J. Chem. Phys. 2005, 122, 014506
22. Tielrooij, K. J.; Timmer, R. L. A.; Bakker, H. J.; Bonn, M. Structure Dynamics of the Proton in Liquid Water Probed with Terahertz Time-Domain Spectroscopy Phys. Rev. Lett. 2009, 102, 198303
23. Chen, H.; Voth, G. A.; Agmon, N. Kinetics of Proton Migration in Liquid Water J. Phys. Chem. B 2010, 114, 333-339
24. Petersen, M. K.; Voth, G. A. Amphiphilic Character of the Hydrated Proton in Methanol-Water Solutions J. Phys. Chem. B 2006, 110, 7085-7089
25. Morrone, J. A.; Haslinger, K. E.; Tuckerman, M. E. Ab Initio Molecular Dynamics Simulation of the Structure and Proton Transport Dynamics of Methanol-Water Solutions J. Phys. Chem. B 2006, 110, 3712-3720
26. 2O Solutions J. Phys. Chem. A 2011, 115, 4063-4075
27. Bonn, M.; Bakker, H. J.; Rago, G.; Pouzy, F.; Siekierzycka, J. R.; Brouwer, A. M.; Bonn, D. Suppression of Proton Mobility by Hydrophobic Hydration J. Am. Chem. Soc. 2009, 131, 17070-17071
28. Rezus, Y. L. A.; Bakker, H. J. Observation of Immobilized Water Molecules around Hydrophobic Groups Phys. Rev. Lett. 2007, 99, 148301
29. Bakulin, A. A.; Liang, C.; Jansen, T. L. C.; Wiersma, D. A.; Bakker, H. J.; Pshenichnikov, M. S. Hydrophobic Solvation: A 2D IR Spectroscopic Inquest Acc. Chem. Res. 2009, 42, 1229-1238
30. Tielrooij, K.-J.; Hunger, J.; Buchner, R.; Bonn, M.; Bakker, H. J. Influence of Concentration and Temperature on the Dynamics of Water in the Hydrophobic Hydration Shell of Tetramethylurea J. Am. Chem. Soc. 2010, 132, 15671-15678
31. Frank, H. S.; Evans, M. W. Free Volume and Entropy in Condensed Systems III. Entropy in Binary Liquid Mixtures; Partial Molal Entropy in Dilute Solutions; Structure and Thermodynamics in Aqueous Electrolytes J. Chem. Phys. 1945, 13, 507-532
32. Rossky, P. J.; Karplus, M. Solvation. A Molecular Dynamics Study of a Dipeptide in Water J. Am. Chem. Soc. 1979, 101, 1913-1937
33. Blokzijl, W.; Engberts, J. B. F. N. Hydrophobic Effects. Opinions and Facts Angew. Chem., Int. Ed. 1993, 32, 1545-1579
34. Haselmeier, R.; Holz, M.; Marbach, W.; Weingaertner, H. Water Dynamics near a Dissolved Noble Gas. First Direct Experimental Evidence for a Retardation Effect J. Phys. Chem. 1995, 99, 2243-2246
35. Shimizu, A.; Fumino, K.; Yukiyasu, K.; Taniguchi, Y. NMR Studies on Dynamic Behavior of Water Molecule in Aqueous Denaturant Solutions at 25 C: Effects of Guanidine Hydrochloride, Urea and Alkylated Ureas J. Mol. Liq. 2000, 85, 269-278
36. Dixit, S.; Crain, J.; Poon, W. C. K.; Finney, J. L.; Soper, A. K. Molecular Segregation Observed in a Concentrated Alcohol-Water Solution Nature 2002, 416, 829-832
37. Dixit, S.; Soper, A. K.; Finney, J. L.; Crain, J. Water Structure and Solute Association in Dilute Aqueous Methanol Europhys. Lett. 2002, 59, 377-383
38. Guo, J. H.; Luo, Y.; Augustsson, A.; Kashtanov, S.; Rubensson, J. E.; Shuh, D. K.; Ågren, H.; Nordgren, J. Molecular Structure of Alcohol-Water Mixtures Phys. Rev. Lett. 2003, 91, 157401
39. Buchanan, P.; Aldiwan, N.; Soper, A. K.; Creek, J. L.; Koh, C. A. Decreased Structure on Dissolving Methane in Water Chem. Phys. Lett. 2005, 415, 89-93
40. Dougan, L.; Bates, S. P.; Hargreaves, R.; Fox, J. P.; Crain, J.; Finney, J. L.; Réat, V.; Soper, A. K. Methanol-Water Solutions: A Bi-Percolating Liquid Mixture J. Chem. Phys. 2004, 121, 6456-6462
41. Ball, P. Water as an Active Constituent in Cell Biology Chem. Rev. 2008, 108, 74-108
42. Qvist, J.; Halle, B. Thermal Signature of Hydrophobic Hydration Dynamics J. Am. Chem. Soc. 2008, 130, 10345-10353
43. Laage, D.; Stirnemann, G.; Hynes, J. T. Why Water Reorientation Slows without Iceberg Formation around Hydrophobic Solutes J. Phys. Chem. B 2009, 113, 2428-2435
44. Perera, P. N.; Fega, K. R.; Lawrence, C.; Sundstrom, E. J.; Tomlinson-Phillips, J.; Ben-Amotz, D. Observation of Water Dangling OH Bonds around Dissolved Nonpolar Groups Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 12230-12234
45. Kuffel, A.; Zielkiewicz, J. The Hydrogen Bond Network Structure within the Hydration Shell around Simple Osmolytes: Urea, Tetramethylurea, and Trimethylamine-N-oxide, Investigated Using Both a Fixed Charge and a Polarizable Water Model J. Chem. Phys. 2010, 133, 035102
46. Stirnemann, G.; Sterpone, F.; Laage, D. Dynamics of Water in Concentrated Solutions of Amphiphiles: Key Roles of Local Structure and Aggregation J. Phys. Chem. B 2011, 115, 3254-3262
47. Majima, H.; Peters, E.; Awakura, Y.; Park, S.; Aoki, M. Electrical Conductivity of Acidic Chloride Solutions Metall. Trans. B 1988, 19, 53-58
48. Agmon, N. Elementary Steps in Excited-State Proton Transfer J. Phys. Chem. A 2005, 109, 13-35
49. Dix, J. A.; Verkman, A. S. Crowding Effects on Diffusion in Solutions and Cells Annu. Rev. Biophys. 2008, 37, 247-263
50. 2O Solutions J. Phys. Chem. 1981, 85, 3480-3493
51. 2O Solvent Isotope Effects on Apparent and Partial Molar Volumes of 1,3-Dimethylurea and Tetramethylurea Solutions J. Chem. Eng. Data 1996, 41, 249-253
52. Markovitch, O.; Chen, H.; Izvekov, S.; Paesani, F.; Voth, G. A.; Agmon, N. Special Pair Dance and Partner Selection: Elementary Steps in Proton Transport in Liquid Water J. Phys. Chem. B 2008, 112, 9456-9466
53. Swanson, J. M. J.; Simons, J. Role of Charge Transfer in the Structure and Dynamics of the Hydrated Proton J. Phys. Chem. B 2009, 113, 5149-5161
54. Schmitt, U. W.; Voth, G. A. Multistate Empirical Valence Bond Model for Proton Transport in Water J. Phys. Chem. B 1998, 102, 5547-5551
55. Schmitt, U. W.; Voth, G. A. The Computer Simulation of Proton Transport in Water J. Chem. Phys. 1999, 111, 9361-9381
56. Day, T. J. F.; Soudackov, A. V.; Cuma, M.; Schmitt, U. W.; Voth, G. A. A Second Generation Multistate Empirical Valence Bond Model for Proton Transport in Aqueous Systems J. Chem. Phys. 2002, 117, 5839-5849
57. Wu, Y. J.; Chen, H. N.; Wang, F.; Paesani, F.; Voth, G. A. An Improved Multistate Empirical Valence Bond Model for Aqueous Proton Solvation and Transport J. Phys. Chem. B 2008, 112, 467-482
58. Addition and Correction. J. Phys. Chem. B 2008, 112, 7146.
59. Belletato, P.; Freitas, L. C. G.; Areîas, E. P. G.; Santos, P. S. Computer Simulation of Liquid Tetramethylurea and Its Aqueous Solution Phys. Chem. Chem. Phys. 1999, 1, 4769-4776
60. Duffy, E. M.; Severance, D. L.; Jorgensen, W. L. Urea: Potential Functions, log P, and Free Energy of Hydration Isr. J. Chem. 1993, 33, 323-330
61. Wang, F.; Voth, G. A. A Linear-Scaling Self-Consistent Generalization of the Multistate Empirical Valence Bond Method for Multiple Excess Protons in Aqueous Systems J. Chem. Phys. 2005, 122, 144105
62. Wang, F.; Izvekov, S.; Voth, G. A. Unusual "Amphiphilic" Association of Hydrated Protons in Strong Acid Solution J. Am. Chem. Soc. 2008, 130, 3120-3126
63. Holz, M.; G., R.; Sacco, A.; Meleleo, A. Nuclear Magnetic Resonance Study of Self-Association of Small Hydrophobic Solutes in Water: Salt Effects and the Lyotropic Series J. Chem. Soc., Faraday Trans. 1993, 89, 1215-1222
64. Marcus, Y. Preferential Solvation in Mixed Solvents. Part 11. Eight Additional Completely Miscible Aqueous Co-Solvent Binary Mixtures and the Relationship between the Volume-Corrected Preferential Solvation Parameters and the Structures of the Co-Solvents Phys. Chem. Chem. Phys. 2002, 4, 4462-4471
65. Almásy, L.; Len, A.; Székely, N. K.; Pleštil, J. Solute Aggregation in Dilute Aqueous Solutions of Tetramethylurea Fluid Phase Equilib. 2007, 257, 114-119
66. Rezus, Y. L. A.; Bakker, H. J. Effect of Urea on the Structural Dynamics of Water Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 18417-18420
67. Hayashi, Y.; Katsumoto, Y.; Omori, S.; Kishii, N.; Yasuda, A. Liquid Structure of the Urea-Water System Studied by Dielectric Spectroscopy J. Phys. Chem. B 2007, 111, 1076-1080
68. Blandamer, M. J.; Engberts, J. B. F. N.; Gleeson, P. T.; Reis, J. C. R. Activity of Water in Aqueous Systems; A Frequently Neglected Property Chem. Soc. Rev. 2005, 34, 440-458
69. Gosting, L. J.; Akeley, D. F. A Study of the Diffusion of Urea in Water at 25 with the Gouy Interference Method J. Am. Chem. Soc. 1952, 74, 2058-2060
70. Leiter, H.; Patil, K. J.; Hertz, H. G. Search for Hydrophobic Association between Small Aprotic Solutes from an Application of the Nuclear Magnetic Relaxation Method J. Solution Chem. 1983, 12, 503-517
71. Saxton, M. J. A Biological Interpretation of Transient Anomalous Subdiffusion. I. Qualitative Model Biophys. J. 2007, 92, 1178-1191
72. Banks, D. S.; Fradin, C. Anomalous Diffusion of Proteins due to Molecular Crowding Biophys. J. 2005, 89, 2960-2971
73. Bronstein, I.; Israel, Y.; Kepten, E.; Mai, S.; Shav-Tal, Y.; Barkai, E.; Garini, Y. Transient Anomalous Diffusion of Telomeres in the Nucleus of Mammalian Cells Phys. Rev. Lett. 2009, 103, 018102
74. Wu, Y.; Tepper, H. L.; Voth, G. A. Flexible Simple Point-Charge Water Model with Improved Liquid-State Properties J. Chem. Phys. 2006, 124, 024503
75. Agmon, N. Tetrahedral Displacement: The Molecular Mechanism behind the Debye Relaxation in Water J. Phys. Chem. 1996, 100, 1072-1080
76. Schmitt, U. W.; Voth, G. A. Quantum Properties of the Excess Proton in Liquid Water Isr. J. Chem. 1999, 39, 483-492
77. Xu, J.; Izvekov, S.; Voth, G. A. Structure and Dynamics of Concentrated Hydrochloric Acid Solutions J. Phys. Chem. B 2010, 114, 9555-9562
78. Petersen, M. K.; Iyengar, S. S.; Day, T. J. F.; Voth, G. A. The Hydrated Proton at the Water Liquid/Vapor Interface J. Phys. Chem. B 2004, 108, 14804-14806
79. Buch, V.; Milet, A.; Vacha, R.; Jungwirth, P.; Devlin, J. P. Water Surface is Acidic Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 7342-7347
80. Chen, H.; Xu, J.; Voth, G. A. Unusual Hydrophobic Interactions in Acidic Aqueous Solutions J. Phys. Chem. B 2009, 113, 7291-7297
81. Iuchi, S.; Chen, H.; Paesani, F.; Voth, G. A. Hydrated Excess Proton at Water-Hydrophobic Interfaces J. Phys. Chem. B 2009, 113, 4017-4030
82. Petersen, P. B.; Saykally, R. J. Evidence for an Enhanced Hydronium Concentration at the Liquid Water Surface J. Phys. Chem. B 2005, 109, 7976-7980
83. Tarbuck, T. L.; Ota, S. T.; Richmond, G. L. Spectroscopic Studies of Solvated Hydrogen and Hydroxide Ions at Aqueous Surfaces J. Am. Chem. Soc. 2006, 128, 14519-14527
84. Tian, C.; Ji, N.; Waychunas, G. A.; Shen, Y. R. Interfacial Structures of Acidic and Basic Aqueous Solutions J. Am. Chem. Soc. 2008, 130, 13033-13039
85. Casieri, C.; Monaco, A.; De Luca, F. Evidence of Temperature-Induced Subdiffusion of Water on the Micrometer Scale in a Nafion Membrane Macromolecules 2009, 43, 638-642
86. Gucker, F. T., Jr.; Gage, F. W.; Moser, C. E. The Densities of Aqueous Solutions of Urea at 25 and 30 and the Apparent Molal Volume of Urea J. Am. Chem. Soc. 1938, 60, 2582-2588
87. Okpala, C.; Guiseppi-Elie, A.; Maharajh, D. M. Several Properties of 1,1,3,3-Tetramethylurea-Water Systems J. Chem. Eng. Data 1980, 25, 384-386
88. Kokubo, H.; Pettitt, B. M. Preferential Solvation in Urea Solutions at Different Concentrations: Properties from Simulation Studies J. Phys. Chem. B 2007, 111, 5233-5242