Thermodynamic Profiles of Salt Effects on a Host-Guest System: New Insight into the Hofmeister Effect

Journal of Physical Chemistry B

Volumn 119, Issue 17, 2015, Pages 5624-5638

  Gibb, Corinne L D ^a   Oertling, Estelle E ^a   Velaga, Santhosh ^a   Gibb, Bruce C ^a  

^a Tulane University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLATION; THERMODYNAMICS;

COMPETITIVE BINDING; HOFMEISTER EFFECTS; HOFMEISTER SERIES; HYDROPHOBIC POCKETS; ISOTHERMAL TITRATION CALORIMETRY; LOW CONCENTRATIONS; THERMODYNAMIC PROFILES; THERMODYNAMICS OF BINDINGS;

SALTS;

CARBOXYLIC ACID; INORGANIC SALT;

CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; THERMODYNAMICS;

CARBOXYLIC ACIDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; SALTS; THERMODYNAMICS;

EID: 84928969134     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/acs.jpcb.5b01708     Document Type: Article

References (95)

1. Schmandt, B.; Jacobsen, S. D.; Becker, T. W.; Liu, Z.; Dueker, K. G. Earth's Interior. Dehydration Melting at the Top of the Lower Mantle Science 2014, 344 (6189) 1265-8
2. Hofmeister, F. Zur Lehre Von Der Wirkung Der Salze (Title Translation: About the Science of the Effect of Salts) Arch. Exp. Pathol. Pharmakol. 1888, 24, 247-260
3. Kunz, W.; Lo, N.; Ninham, B. W. The Present State of Affairs with Hofffieister Effects Curr. Opin. Colloid Interface Sci. 2004, 9, 1-18
4. Collins, K. D.; Washabaugh, M. W. The Hofmeister Effect and the Behavior of Water at Interfaces Q. Rev. Biophys. 1985, 18, 323-422
5. Jungwirth, P.; Tobias, J. W. Specific Ion Effects at the Air/Water Interface Chem. Rev. 2006, 106, 1259-1281
6. Ball, P. Water as an Active Constituent in Cell Biology Chem. Rev. 2008, 108, 74-108
7. Lo Nostro, P.; Ninham, B. W.; Milani, S.; Lo Nostro, A.; Pesavento, G.; Baglioni, P. Hofmeister Effects in Supramolecular and Biological Systems Biophys. Chem. 2006, 124 (3) 208-13
8. Jones, G.; Ray, W. A. The Surface Tension of Solutions of Electrolytes as a Function of the Concentration. I. A Differential Method for Measuring Relative Surface Tension J. Am. Chem. Soc. 1937, 59, 187-198
9. Jarvis, N. L.; Scheiman, M. A. Surface Potentials of Aqueous Electrolyte Solutions J. Phys. Chem. 1968, 72, 74-78
10. Hu, J. H.; Shi, Q.; Davidovits, P.; Worsnop, D. R.; M.S, Z.; Kolb, C. E. Reactive Uptake of Cl2(G) and Br2(G) by Aqueous Surfaces as a Function of Br- and I- Ion Concentration: The Effect of Chemical Reaction at the Interface J. Phys. Chem. 1995, 99, 8768-8776
11. Knipping, E. M. Experiments and Simulations of Ion-Enhanced Interfacial Chemistry on Aqueous NaCl Aerosols Science 2000, 288 (5464) 301-306
12. Laskin, A.; Gaspar, D. J.; Wang, W.; Hunt, S. W.; Cowin, J. P.; Colson, S. D.; Finlayson-Pitts, B. J. Reactions at Interfaces as a Source of Sulfate Formation in Sea-Salt Particles Science 2003, 301 (5631) 340-4
13. Onsager, L.; Samaras, N. N. T. The Surface Tension of Debye-Hückel Electrolytes J. Chem. Phys. 1934, 2 (8) 528
14. Liu, D. R.; Ma, G.; Levering, L. M.; Allen, H. C. Vibrational Spectroscopy of Aqueous Sodium Halide Solutions and Air-Liquid Interfaces: Observation of Increased Interfacial Depth J. Phys. Chem. B 2004, 108, 2252-2260
15. Raymond, E. A.; Richmond, G. L. Probing the Molecular Structure and Bonding of the Surface of Aqueous Salt Solutions J. Phys. Chem. B 2004, 108, 5051-5059
16. Petersen, P. B.; Saykally, R. J. On the Nature of Ions at the Liquid Water Surface Annu. Rev. Phys. Chem. 2006, 57, 333-64
17. Verreault, D.; Allen, H. C. Bridging the Gap between Microscopic and Macroscopic Views of Air/Aqueous Salt Interfaces Chem. Phys. Lett. 2013, 586, 1-9
18. Jungwirth, P.; Tobias, D. J. Ions at the Air/Water Interface J. Phys. Chem. B 2002, 106, 6361-6373
19. Petersen, P. B.; Saykally, R. J.; Mucha, M.; Jungwirth, P. Enhanced Concentration of Polarizable Anions at the Liquid Water Surface: SHG Spectroscopy and MD Simulations of Sodium Thiocyanide J. Phys. Chem. B 2005, 109, 10915-10921
20. Poiseuille, J. M. L. Experimental Investigations on the Flow of Liquids in Tubes of Very Small Diameter Ann. Chim. Phys. 1847, 21, 76
21. Cox, W. M.; Wolfenden, J. H. The Viscosity of Strong Electrolytes Measured by a Differential Method Proc. R. Soc. A: Math., Phys. Eng. Sci. 1934, 145 (855) 475-488
22. Gurney, R. W. Ionic Processes in Solution; McGraw-Hill: New York, 1953.
23. Jenkins, H. D. B.; Marcus, Y. Viscosity B-Coefficients of Ions in Solution Chem. Rev. 1995, 95, 2695-2724
24. Dillon, S. R.; Dougherty, R. C. Raman Studies of the Solution Structure of Univalent Electrolytes in Water J. Phys. Chem. A 2002, 102, 7647-7650
25. Dougherty, R. C. Density of Salt Solutions: Effect of Ions on the Apparent Density of Water J. Phys. Chem. B 2001, 105, 4514-4519
26. Mancinelli, R.; Botti, A.; Bruni, F.; Ricci, M. A.; Soper, A. K. Perturbation of Water Structure Due to Monovalent Ions in Solution Phys. Chem. Chem. Phys. 2007, 9 (23) 2959
27. Hamaguchi, K.; Geiduschek, E. P. The Effect of Electrolytes on the Stability of the Deoxyribonucleate Helix J. Am. Chem. Soc. 1962, 84, 1329-1338
28. Tielrooij, K. J.; Garcia-Araez, N.; Bonn, M.; Bakker, H. J. Cooperativity in Ion Hydration Science 2010, 328, 1006-1009
29. Omta, A. W.; Kropman, M. F.; Woutersen, S.; Bakker, H. J. Negligible Effect of Ions on the Hydrogen-Bond Structure in Liquid Water Science 2003, 301, 347-349
30. Moilanen, D. E.; Wong, D.; Rosenfeld, D. E.; Fenn, E. E.; Fayer, M. D. Ion-Water Hydrogen-Bond Switching Observed with 2D IR Vibrational Echo Chemical Exchange Spectroscopy Proc. Natl. Acad. Sci. U.S.A. 2009, 106 (2) 375-380
31. Turton, D. A.; Hunger, J.; Hefter, G.; Buchner, R.; Wynne, K. Glasslike Behavior in Aqueous Electrolyte Solutions J. Chem. Phys. 2008, 128 (16) 161102
32. Wachter, W.; Kunz, W.; Buchner, R. Is there an Anionic Hofmeister Effect on Water Dynamics? Dielectric Spectroscopy of Aqueous Solutions of NaBr, NaI, NaNO3, NaClO4, and NaSCN J. Phys. Chem. A 2005, 109, 8675-8683
33. Funkner, S.; Niehues, G.; Schmidt, D. A.; Heyden, M.; Schwaab, G.; Callahan, K. M.; Tobias, D. J.; Havenith, M. Watching the Low-Frequency Motions in Aqueous Salt Solutions: The Terahertz Vibrational Signatures of Hydrated Ions J. Am. Chem. Soc. 2012, 134 (2) 1030-5
34. Bello, J.; Bello, H. R. Interactions of Model Peptides with Water and Lithium Bromide Nature 1961, 190, 440-441
35. Bello, J.; Bello, H. R. Evidence from Model Peptides Relating to the Denaturation of Proteins by Lithium Salts Nature 1962, 194, 681-682
36. von Hippel, P.; Peticolas, V.; Schack, L.; Karlson, L. Model Studies on the Effects of Neutral Salts on the Conformational Stability of Biological Macromolecules. I. Ion Binding to Polyacrylamide and Polystyrene Columnst Biochemistry 1973, 12, 1256-1264
37. Kunz, W.; Lo Nostro, P.; Ninham, B. W. The Present State of Affairs with Hofmeister Effects Curr. Opin. Colloid Interface Sci. 2004, 9 (1-2) 1-18
38. Jungwirth, P.; Cremer, P. S. Beyond Hofmeister Nat. Chem. 2014, 6 (4) 261-3
39. Jungwirth, P.; Winter, B. Ions at Aqueous Interfaces: From Water Surface to Hydrated Proteins Annu. Rev. Phys. Chem. 2008, 59, 343-66
40. Zhang, Y.; Cremer, P. S. Interactions between Macromolecules and Ions: The Hofmeister Series Curr. Opin. Chem. Biol. 2006, 10, 658-663
41. Pegram, L. M.; Record, M. T. J. Hofmeister Salt Effects on Surface Tension Arise from Partitioning of Anions and Cations between Bulk Water and the Air-Water Interface J. Phys. Chem. B 2007, 111, 5411-5417
42. Pegram, L. M.; Wendorffa, T.; Erdmanna, R.; Shkela, I.; Bellissimoa, D.; Felitskya, D. J.; Record, M. T. J. Why Hofmeister Effects of many Salts Favor Protein Folding but not DNA Helix Formation Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 7716-7721
43. Pegram, L. M.; Record, M. T. J. Quantifying Accumulation or Exclusion of H+, HO-, and Hofmeister Salt Ions near Interfaces Chem. Phys. Lett. 2008, 467, 1-8
44. Zangi, R.; Hagen, M.; Berne, B. J. Effect of Ions on the Hydrophobic Interaction between Two Plates J. Am. Chem. Soc. 2007, 129, 4678-4686
45. Xie, W. J.; Gao, Y. Q. A Simple Theory for the Hofmeister Series J. Phys. Chem. Lett. 2013, 4, 4247-4252
46. Gao, Y. Q. Simple Theory for Salt Effects on the Solubility of Amide J. Phys. Chem. B 2012, 116, 9934-9943
47. Zhang, Y.; Furyk, S.; Bergbreiter, D. E.; Cremer, P. S. Specific Ion Effects on the Water Solubility of Macromolecules: PNIPAM and the Hofmeister Series J. Am. Chem. Soc. 2005, 127, 14505-14510
48. Zhang, Y. J.; Cremer, P. S. Chemistry of Hofmeister Anions and Osmolytes Annu. Rev. Phys. Chem. 2010, 61, 63-83
49. Rembert, K. B.; Paterova, J.; Heyda, J.; Hilty, C.; Jungwirth, P.; Cremer, P. S. Molecular Mechanisms of Ion-Specific Effects on Proteins J. Am. Chem. Soc. 2012, 134, 10039-10046
50. Paterová, J.; Rembert, K. B.; Heyda, J.; Kurra, Y.; Okur, H. I.; Liu, W. R.; Hilty, C.; Cremer, P. S.; Jungwirth, P. Reversal of the Hofmeister Series: Specific Ion Effects on Peptides J. Phys. Chem. B 2013, 117 (27) 8150-8
51. Muller, K.; Faeh, C.; Diederich, F. Fluorine in Pharmaceuticals: Looking Beyond Intution Science 2007, 317, 1881-1886
52. Sessler, J. L.; Gale, P. A.; Cho, W.-S. Anion Receptor Chemistry; Royal Society of Chemistry: Cambridge, U.K., 2006.
53. Gale, P. A.; Busschaert, N.; Haynes, C. J.; Karagiannidis, L. E.; Kirby, I. L. Anion Receptor Chemistry: Highlights from 2011 and 2012 Chem. Soc. Rev. 2013, 43, 205-241
54. Davis, J. G.; Gierszal, K. P.; Wang, P.; Ben-Amotz, D. Water Structural Transformation at Molecular Hydrophobic Interfaces Nature 2012, 491, 582-5
55. Rankin, B. M.; Ben-Amotz, D. Expulsion of Ions from Hydrophobic Hydration Shells J. Am. Chem. Soc. 2013, 135 (24) 8818-21
56. Pegram, L. M.; Record, M. T. J. Thermodynamic Origin of Hofmeister Ion Effects J. Phys. Chem. B 2008, 112, 9428-9436
57. Carnagie, R.; Gibb, C. L. D.; Gibb, B. C. Anion Complexation and the Hofmeister Effect Angew. Chem., Int. Ed. 2014, 53 (43) 11498-11500
58. Gibb, C. L.; Gibb, B. C. Anion Binding to Hydrophobic Concavity Is Central to the Salting-in Effects of Hofmeister Chaotropes J. Am. Chem. Soc. 2011, 133, 7344-7347
59. Harries, D.; Rau, D. C.; Parsegian, V. A. Solutes Probe Hydration in Specific Association of Cyclodextrin and Adamantane J. Am. Chem. Soc. 2005, 127, 2184-2190
60. Terekhova, I. V.; Romanova, A. O.; Kumeev, R. S.; Fedorov, M. V. Selective Na+/K+ Effects on the Formation of β-Cyclodextrin Complexes with Aromatic Carboxylic Acids: Competition for the Guest J. Phys. Chem. B 2010, 114, 12607-12613
61. Gibb, C. L. D.; Gibb, B. C. Well Defined, Organic Nano-Environments in Water: The Hydrophobic Effect Drives a Capsular Assembly J. Am. Chem. Soc. 2004, 126, 11408-11409
62. Liu, S.; Whisenhunt-Ioup, S. E.; Gibb, C. L. D.; Gibb, B. C. An Improved Synthesis of 'Octa-Acid' Deep-Cavity Cavitand Supramol. Chem. 2011, 23 (6) 480-485
63. Rowan, S. J.; Hamilton, D. G.; Brady, P. A.; Sanders, J. K. M. Automated Recognition, Sorting, and Covalent Self-Assembly by Predisposed Building Blocks in a Mixture J. Am. Chem. Soc. 1997, 119, 2578-2579
64. Jordan, J. H.; Gibb, B. C. Molecular Containers Assembled through the Hydrophobic Effect Chem. Soc. Rev. 2015, 44, 547-585
65. Laughrey, Z.; Gibb, B. C. Water-Soluble, Self-Assembling Container Molecules: An Update Chem. Soc. Rev. 2011, 40 (1) 363-86
66. Gibb, C. L. D.; Gibb, B. C. Templated Assembly of Water-Soluble Nano-Capsules: Inter-Phase Sequestration, Storage, and Separation of Hydrocarbon Gases J. Am. Chem. Soc. 2006, 128 (51) 16498-16499
67. Liu, S.; Gan, H.; Hermann, A. T.; Rick, S. W.; Gibb, B. C. Kinetic Resolution of Constitutional Isomers Controlled by Selective Protection inside a Supramolecular Nanocapsule Nat. Chem. 2010, 2 (10) 847-852
68. Kaanumalle, L. S.; Gibb, C. L. D.; Gibb, B. C.; Ramamurthy, V. Controlling Photochemistry with Distinct Hydrophobic Nano-Environments J. Am. Chem. Soc. 2004, 126, 14366-14367
69. Kaanumalle, L. S.; Gibb, C. L. D.; Gibb, B. C.; Ramamurthy, V. A Hydrophobic Nano-Capsule Controls the Photophysics of Aromatic Molecules by Suppressing Their Favored Solution Pathways J. Am. Chem. Soc. 2005, 127, 3674-3675
70. Kaanumalle, L. S.; Gibb, C. L. D.; Gibb, B. C.; Ramamurthy, V. Photo-Fries Reaction in Water Made Selective with a Capsule Org. Biomol. Chem. 2007, 5, 236-238
71. Natarajan, A.; Kaanumalle, L. S.; Jockusch, S.; Gibb, C. L. D.; Gibb, B. C.; Turro, N. J.; Ramamurthy, V. Controlling Photoreactions with Restricted Spaces and Weak Intermolecular Forces: Remarkable Product Selectivity During Oxidation of Olefins by Singlet Oxygen J. Am. Chem. Soc. 2007, 129, 4132-4133
72. Gibb, C. L. D.; Sundaresan, A. K.; Ramamurthy, V.; Gibb, B. C. Templation of the Excited-State Chemistry of Α(n -Alkyl) Dibenzyl Ketones: How Guest Packing with a Nanoscale Supramolecular Capsule Influences Photochemistry J. Am. Chem. Soc. 2008, 130, 4069-4080
73. Sundaresan, A. K.; Gibb, C. L. D.; Gibb, B. C.; Ramamurthy, V. Chiral Photochemistry in a Confined Space: Torquoselective Photoelectrocyclization of Pyridones within an Achiral Hydrophobic Capsule Tetrahedron 2009, 65, 7277-7288
74. Sundaresan, A. K.; Kaanumalle, L. S.; Gibb, C. L. D.; Gibb, B. G.; Ramamurthy, V. Chiral Photochemistry within a Confined Space: Diastereoselective Photorearrangements of a Tropolone and a Cyclohexadienone Included in a Synthetic Cavitand Dalton Trans. 2009, 20, 4003-4011
75. Gibb, C. L. D.; Gibb, B. C. Binding of Cyclic Carboxylates to Octa-Acid Deep-Cavity Cavitand J. Comput.-Aided Mol. Des. 2014, 28 (4) 319-325
76. Gan, H.; Gibb, B. C. ITC Analysis of Guest Binding to a Deep-Cavity Cavitand Supramol. Chem. 2010, 22, 808-814
77. Sun, H.; Gibb, C. L. D.; Gibb, B. C. Calorimetric Analysis of the 1:1 Complexes Formed between a Water-Soluble Deep-Cavity Cavitand, and Cyclic and Acyclic Carboxylic Acids Supramol. Chem. 2008, 20 (1-2) 141-147
78. Ewell, J.; Gibb, B. C.; Rick, S. W. Water inside a Hydrophobic Cavitand Molecule J. Phys. Chem. B 2008, 112, 10272-10279
79. Biedermann, F.; Nau, W. M.; Schneider, H. J. The Hydrophobic Effect Revisited - Studies with Supramolecular Complexes Imply High-Energy Water as a Noncovalent Driving Force Angew. Chem., Int. Ed. 2014, 53 (42) 11158-71
80. Baron, R.; Setny, P.; McCammon, J. A. Water in Cavity-Ligand Recognition J. Am. Chem. Soc. 2010, 132 (34) 12091-7
81. Setny, P.; Baron, R.; McCammon, J. A. How Can Hydrophobic Association Be Enthalpy Driven? J. Chem. Theory Comput. 2010, 6, 2866-2871
82. Moghaddam, S.; Yang, C.; Rekharsky, M.; Ko, Y. H.; Kim, K.; Inoue, Y.; Gilson, M. K. New Ultrahigh Affinity Host-Guest Complexes of Cucurbit[7]uril with Bicyclo[2.2.2]Octane and Adamantane Guests: Thermodynamic Analysis and Evaluation of M2 Affinity Calculations J. Am. Chem. Soc. 2011, 133 (10) 3570-81
83. Biedermann, F.; Uzunova, V. D.; Scherman, O. A.; Nau, W. M.; De Simone, A. Release of High-Energy Water as an Essential Driving Force for the High-Affinity Binding of Cucurbit[n]urils J. Am. Chem. Soc. 2012, 134 (37) 15318-23
84. Biedermann, F.; Vendruscolo, M.; Scherman, O. A.; De Simone, A.; Nau, W. M. Cucurbit[8]Uril and Blue-Box: High-Energy Water Release Overwhelms Electrostatic Interactions J. Am. Chem. Soc. 2013, 135 (39) 14879-88
85. Wanjari, P. P.; Gibb, B. C.; Ashbaugh, H. S. Simulation Optimization of Spherical Non-Polar Guest Recognition by Deep-Cavity Cavitands J. Chem. Phys. 2013, 139 (23) 234502
86. Wiseman, T.; Williston, S.; Brandts, J. F.; Lin, L.-N. Rapid Measurement of Binding Constants and Heats of Binding Using a New Titration Calorimeter Anal. Biochem. 1989, 179, 131-139
87. Turnbull, W. B.; Daranas, A. H. On the Value of c: Can Low Affinity Systems Be Studied by Isothermal Titration Calorimetry? J. Am. Chem. Soc. 2003, 125, 14859-14866
88. Tellinghuisen, J. Isothermal Titration Calorimetry at Very Low c Anal. Biochem. 2008, 373, 395-397
89. Tellinghuisen, J. Optimizing Experimental Parameters in Isothermal Titration Caloriemetry: Variable Volume Procedures J. Phys. Chem. B 2007, 111, 11531-11537
90. Tellinghuisen, J. Designing Isothermal Titration Calorimetry Experiments for the Study of 1:1 Binding: Problems with the "Standard Protocol" Anal. Biochem. 2012, 424 (2) 211-20
91. Gibb, C. L. D.; Stevens, E. D.; Gibb, B. C. C-H···X-R Hydrogen Bonds Drive the Complexation Properties of a Nano-Scale Molecular Basket J. Am. Chem. Soc. 2001, 123, 5849-5850
92. Laughrey, Z. R.; Upton, T.; Gibb, B. C. A Deuterated Host Confirms the Importance of C-H···X-R Hydrogen Bonds in Guest Binding to Deep-Cavity Cavitands Chem. Commun. 2006, 970-972
93. Laughrey, Z. R.; Gibb, C. L. D.; Senechal, T.; Gibb, B. C. Guest Binding and Orientation within Open Molecular Hosts Possessing Deep Crowns of Acidic C-H Groups Chem.-Eur. J. 2003, 9, 130-139
94. Ben-Amotz, D.; Underwood, R. Unraveling Water's Entropic Mysteries: A Unified View of Nonpolar, Polar, and Ionic Hydration Acc. Chem. Res. 2008, 41 (8) 957-67
95. Kherb, J.; Flores, S. C.; Cremer, P. S. Role of Carboxylate Side Chains in the Cation Hofmeister Series J. Phys. Chem. B 2012, 116 (25) 7389-97