Effect of the hydrophobic alcohol chain length on the hydrogen-bond network of water

Journal of Physical Chemistry B

Volumn 118, Issue 29, 2014, Pages 8750-8755

  Juurinen, Iina ^a   Pylkkänen, Tuomas ^a   Sahle, Christoph J ^a   Simonelli, Laura ^b   Hämäläinen, Keijo ^a   Huotari, Simo ^a   Hakala, Mikko ^a  

^a Department of Physics ^*  (Finland)

^b EUROPEAN SYNCHROTRON RADIATION FACILITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN BONDS; HYDROPHOBICITY;

ALCOHOL MOLECULES; HYDROGEN BOND NETWORKS; HYDROPHOBIC ALCOHOLS; HYDROPHOBIC GROUPS; LINEAR ALCOHOLS; MICROSCOPIC STRUCTURES; WATER-ALCOHOL MIXTURES; X-RAY RAMAN SCATTERINGS;

PROPANOL;

ALCOHOL DERIVATIVE; WATER;

CHEMICAL PHENOMENA; CHEMISTRY; CONFORMATION; HYDROGEN BOND; MOLECULAR DYNAMICS; X RAY DIFFRACTION;

ALCOHOLS; HYDROGEN BONDING; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MOLECULAR CONFORMATION; MOLECULAR DYNAMICS SIMULATION; WATER; X-RAY DIFFRACTION;

EID: 84905027734     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp5045332     Document Type: Article

References (72)

1. Ball, P. Water as an Active Constituent in Cell Biology Chem. Rev. 2008, 108, 74-108
2. Pal, S. K.; Zewail, A. H. Dynamics of Water in Biological Recognition Chem. Rev. 2004, 104, 2099-2123
3. 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, 507-531
4. Turner, J.; Soper, A. K. The Effect of Apolar Solutes on Water-Structure-Alcohols and Tetraalkylammonium Ions J. Chem. Phys. 1994, 101, 6116-6125
5. Finney, J. L.; Turner, J. Direct Measurement by Neutron Diffraction of the Solvation of Polar and Apolar Molecules. The Hydration of the Tetramethylammonium Ion Faraday Discuss. Chem. Soc. 1988, 85, 125-135
6. Turner, J.; Soper, A. K.; Finney, J. L. A Neutron-Diffraction Study of Tetramethylammonium Chloride in Aqueous Solution Mol. Phys. 1990, 70, 679-700
7. 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, 1129-1238
8. 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
9. Rezus, Y. L. A.; Bakker, H. J. Observation of Immobilized Water Molecules around Hydrophobic Groups Phys. Rev. Lett. 2007, 99 (14301) 1-4
10. Stirnemann, G.; Hynes, J. T.; Laage, D. Water Hydrogen Bond Dynamics in Aqueous Solutions of Amphiphiles J. Phys. Chem. B 2010, 114, 3052-3059
11. 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
12. Lambeth, B. P.; Junghans, C.; Kremer, K.; Clementi, C.; Site, L. D. Communication: On the Locality of Hydrogen Bond Networks at Hydrophobic Interfaces J. Chem. Phys. 2010, 133 (221101) 1-4
13. Silvestrelli, P. L. Are There Immobilized Water Molecules around Hydrophobic Groups? Aqueous Solvation of Methanol from First Principles J. Phys. Chem. B 2009, 113, 10728-10731
14. Davis, J. G.; Gierszal, K. P.; Wang, P.; Ben-Amotz, D. Water Structural Transformation at Molecular Hydrophobic Interfaces Nature 2012, 491, 582-585
15. Galamba, N. Waters Structure around Hydrophobic Solutes and the Iceberg Model J. Phys. Chem. B 2013, 117, 2153-2159
16. Raschke, T. M.; Levitt, M. Nonpolar Solutes Enchance Water Structure Within Hydration Shells while Reducing Interactions Between Them Proc. Natl. Acad. Sci. 2005, 102, 6777-6782
17. Qvist, J.; Halle, B. Thermal Signature of Hydrophobic Hydration Dynamics J. Am. Chem. Soc. 2008, 130, 10345-10353
18. Tomlinson-Phillips, J.; Davis, J.; Ben-Amotz, D.; Spångberg, D.; Pejov, L.; Hermansson, K. Structure and Dynamics of Water Dangling OH bonds in Hydrophobic Hydration Shells. Comparison of Simulation and Experiment J. Phys. Chem. A 2011, 115, 6177-6183
19. 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
20. Huang, N.; Schlesinger, D.; Nordlund, D.; Huang, C.; Tyliszczak, T.; Weiss, T. M.; Acremann, Y.; Pettersson, L. G. M.; Nilsson, A. Microscopic Probing of the Size Dependence in Hydrophobic Solvation J. Chem. Phys. 2012, 136 (074507) 1-7
21. Garde, S.; Patel, A. J. Unraveling the Hydrophobic Effect, One Molecule at a Time Proc. Natl. Acad. Sci. 2011, 108, 16491-16492
22. King, J. T.; Arthur, E. J.; Brooks, C. L.; Kubarych, K. J. Site-Specific Hydration Dynamics of Globular Proteins and the Role of Constrained Water in Solvent Exchange with Amphiphilic Cosolvents J. Phys. Chem. B 2012, 116, 5604-5611
23. Chandler, D. Interfaces and the Driving Force of Hydrophobic Assembly Nature 2005, 437, 640-647
24. Petersen, C.; Bakulin, A. A.; Pavelyev, V. G.; Pshenichnikov, M. S. Femtosecond Midinfrared Study of Aggregation Behavior in Aqueous Solutions of Amphiphilic Molecules J. Chem. Phys. 2010, 133 (164514) 1-8
25. Bakulin, A. A.; Pshenichnikov, M. S.; Bakker, H. J.; Petersen, C. Hydrophobic Molecules Slow Down the Hydrogen-Bond Dynamics of Water J. Phys. Chem. A 2011, 115, 1821-1829
26. Mazur, K.; Heisler, I. A.; Meech, S. R. Aqueous Solvation of Amphiphilic Solutes: Concentration and Temperature Dependent Study of the Ultrafast Polarisability Relaxation Dynamics Phys. Chem. Chem. Phys. 2012, 14, 6343-6351
27. Rahman, H. M. A.; Hefter, G.; Buchner, R. Hydrophilic and Hydrophobic Hydration of Sodium Propanoate and Sodiun Butanoate in Aqueous Solution J. Phys. Chem. B 2013, 117, 2142-2152
28. Schülke, W. Electron Dynamics by Inelastic X-Ray Scattering; Oxford University Press: Oxford, U. K., 2007.
29. Nilsson, A.; Nordlund, D.; Waluyo, I.; Huang, N.; Ogasawara, H.; Kaya, S.; Bergmann, U.; Näslund, L.-Å.; Öström, H.; Wernet, P. X-ray Absorption Spectroscopy and X-ray Raman Scattering of Water and Ice; an Experimental View J. Electron Spectrosc. Relat. Phenom. 2010, 177, 99-129
30. Wernet, P.; Nordlund, D.; Bergmann, U.; Cavalleri, M.; Odelius, M.; Ogasawara, H.; Näslund, L. Å.; Hirsch, T. K.; Ojamäe, L.; Glatzel, P. The Structure of the First Coordination Shell in Liquid Water Science 2004, 304, 995-999
31. Tse, J. S.; Shaw, D. M.; Klug, D. D.; Patchkovskii, S.; Vankó, G.; Monaco, G.; Krisch, M. X-ray Raman Spectroscopic Study of Water in the Condensed Phases Phys. Rev. Lett. 2008, 100 (095502) 1-4
32. Sahle, C. J.; Sternemann, C.; Schmidt, C.; Lehtola, S.; Jahn, S.; Simonelli, L.; Huotari, S.; Hakala, M.; Pylkkänen, T.; Nyrow, A. Microscopic Structure of Water at Elevated Pressures and Temperatures Proc. Natl. Acad. Sci. U.S.A. 2013, 110, 6301-6306
33. Pylkkänen, T.; Sakko, A.; Hakala, M.; Hämäläinen, K.; Monaco, G.; Huotari, S. Temperature Dependence of the Near-Edge Spectrum of Water J. Phys. Chem. B 2011, 115, 14544-14550
34. Juurinen, I.; Pylkkänen, T.; Ruotsalainen, K. O.; Sahle, C. J.; Monaco, G.; Hämäläinen, K.; Huotari, S.; Hakala, M. Saturation Behavior in X-ray Raman Scattering Spectra of Aqueous LiCl J. Phys. Chem. B 2013, 117, 16506-16511
35. 2O Phys. Rev. Lett. 2005, 94 (025502) 1-4
36. Huang, N.; Nordlund, D.; Huang, C.; Bergmann, U.; Weiss, T. M.; Pettersson, L. G. M.; Nilsson, A. X-ray Raman Scattering Provides Evidence for Interfacial Acetonitrile-Water Dipole Interactions in Aqueous Solutions J. Chem. Phys. 2011, 135 (164509) 1-6
37. Pylkkänen, T.; Giordano, V. M.; Chervin, J.-C.; Sakko, A.; Hakala, M.; Soininen, J. A.; Hämäläinen, K.; Monaco, G.; Huotari, S. Role of Non-Hydrogen-Bonded Molecules in the Oxygen K-Edge Spectrum of Ice J. Phys. Chem. B 2010, 114, 3804-3808
38. Nagasaka, M.; Mochizuki, K.; Leloup, V.; Kosugi, N. Local Structures of Methanol-Water Binary Solutions Studied by Soft X-ray Absorption Spectroscopy J. Phys. Chem. B 2014, 118, 4388-4396
39. Bergmann, U.; Wernet, P.; Glatzel, P.; Cavalleri, M.; Pettersson, L. G. M.; Nilsson, A.; Cramer, S. P. X-ray Raman Spectroscopy at the Oxygen K Edge of Water and Ice: Implications on Local Structure Models Phys. Rev. B 2002, 66 (092107) 1-4
40. Fister, T. T.; Nagle, K. P.; Vila, F. D.; Seidler, G. T.; Hammer, C.; Cross, J. O.; Rehr, J. J. Intermediate-Range Order in Water Ices: Nonresonant Inelastic X-ray Scattering Measurements and Real-Space Full Multiple Scattering Calculations Phys. Rev. B 2009, 79 (174117) 1-7
41. Huang, C.; Wikfeldt, K. T.; Tokushima, T.; Nordlund, D.; Harada, Y.; Bergmann, U.; Niebuhr, M.; Weiss, T. M.; Horikawa, Y.; Leetmaa, M. The Inhomogeneous Structure of Water at Ambient Conditions Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 15214-15218
42. 2O in a Liquid Microjet: Hydrogen Bonds and Nuclear Dynamics Phys. Rev. B 2012, 85 (155104) 1-6
43. Lange, K. M.; Könnecke, R.; Soldatov, M.; Golnak, R.; Rubensson, J.-E.; Soldatov, A.; Aziz, E. F. On the Origin of the Hydrogen-Bond-Network Nature of Water: X-Ray Absorption and Emission Spectra of Water-Acetonitrile Mixtures Angew. Chem., Int. Ed. 2011, 50, 10621-10625
44. Verbeni, R.; Pylkkänen, T.; Huotari, S.; Simonelli, L.; Vankó, G.; Martel, K.; Henriquet, C.; Monaco, G. Multiple-Element Spectrometer for Non-Resonant Inelastic X-ray Spectroscopy of Electronic Excitations J. Synchrotron Radiat. 2009, 16, 469-476
45. Huotari, S.; Pylkkänen, T.; Verdeni, R.; Monaco, G.; Hämäläinen, K. Direct Tomography with Chemical-Bond Contrast Nat. Mater. 2011, 10, 489-493
46. Pylkkänen, T.; Lehtola, J.; Hakala, M.; Sakko, A.; Monaco, G.; Huotari, S.; Hämäläinen, K. Universal Signature of Hydrogen Bonding in the Oxygen K-Edge Spectrum of Alcohols J. Phys. Chem. B 2010, 114, 13076-13083
47. Berendsen, H. J. C.; van der Spoel, D.; van Drunen, R. Gromacs-a Message-Passing Parallel Molecular-Dynamics Implementation Comput. Phys. Commun. 1995, 91, 43-56
48. Jorgensen, W. L.; Chandrasekhar, J.; Madura, J. D.; Impey, R. W.; Klein, M. L. Comparison of Simple Potential Functions for Simulating Liquid Water J. Chem. Phys. 1983, 79, 926-935
49. Jorgensen, W. L.; Maxwell, D. S.; Tirado-Rives, J. Development and Testing of the OPLS All-Atom Force Field on Conformational Energetics and Properties of Organic Liquids J. Am. Chem. Soc. 1996, 118, 11225-11236
50. Lehtola, J.; Hakala, M.; Sakko, A.; Hämäläinen, K. ERKALE-A Flexible Program Package for X-ray Properties of Atoms and Molecules J. Chem. Phys. 2012, 33, 1572-1585
51. Lehtola, S. ERKALE-HF/DFT from Hel (2012). http://erkale.googlecode.com, (accessed Nov 15, 2013).
52. Triguero, L.; Pettersson, L. G. M.; Agren, H. Calculations of Near-Edge X-ray-Absorption Spectra of Gas-Phase and Chemisorbed Molecules by Means of Density-Functional and Transition-Potential Theory Phys. Rev. B 1998, 58, 8097-8110
53. Perdew, J. P.; Burke, K.; Ernzerhof, M. Generalized Gradient Approximation Made Simple Phys. Rev. Lett. 1996, 77, 3865-3868
54. Perdew, J. P.; Burke, K.; Ernzerhof, M. Generalized Gradient Approximation Made Simple Phys. Rev. Lett. 1996, 77, 3865.
55. Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1997, 78, 1396-1396
56. Hammer, B.; Hansen, L. B.; Norskov, J. K. Improved Adsorption Energetics within Density-Functional Theory Using Revised Perdew-Burke-Ernzerhof Functionals Phys. Rev. B 1999, 59, 7413-7421
57. Kutzelnigg, W.; Fleischer, U.; Schindler, M. NMR Basic Principles and Progress; Springer Verlag, Berlin/Heidelberg, 1991; Vol. 213; pp 165-262.
58. Dunning, T. H. Gaussian Basis Sets for Use in Correlated Molecular Calculations. I. The Atoms Boron Through Neon and Hydrogen J. Chem. Phys. 1989, 90, 1007-1023
59. Leetmaa, M.; Ljungberg, M. P.; Lyubartsev, A.; Nilsson, A.; Pettersson, L. G. M. Theoretical Approximations to X-ray Absorption Spectroscopy of Liquid Water and Ice J. Electron Spectrosc. Relat. Phenom. 2010, 177, 135-157
60. Wilson, K. R.; Cavalleri, M.; Rude, B. S.; Schaller, R. D.; Catalano, T.; Nilsson, A.; Saykally, R. J.; Pettersson, L. G. M. X-ray Absorption Spectroscopy of Liquid Methanol Microjets: Bulk Electronic Structure and Hydrogen Bonding Network J. Phys. Chem. B 2005, 109, 10194-10203
61. Guo, J.-H.; Luo, Y.; Augustsson, A.; Kashtanov, S.; Rubensson, J.-E.; Shuh, D.; Zhuang, V.; Ross, P.; Ågren, H.; Nordgren, J. The Molecular Structure of Alcohol-Water Mixtures Determined by Soft-X-ray Absorption and Emission Spectroscopy J. Electron Spectrosc. Relat. Phenom. 2004, 137-140, 425-428
62. Chen, W.; Wu, X.; Car, R. X-ray Absorption Signatures of the Molecular Environment in Water and Ice Phys. Rev. Lett. 2010, 105 (017802) 1-4
63. Nordlund, D.; Ogasawara, H.; Andersson, K. J.; Tatarkhanov, M.; Salmerón, M.; Pettersson, L. G. M.; Nilsson, A. Sensitivity of X-ray Absorption Spectroscopy to Hydrogen Bond Topology Phys. Rev. B 2009, 80 (233404) 1-4
64. Kaya, S.; Schlesinger, D.; Yamamoto, S.; Newberg, J. T.; Bluhm, H.; Ogasawara, H.; Kendelewicz, T.; Brown, G. E.; Pettersson, L. G. M.; Nilsson, A. Highly Compressed Two-Dimensional Form of Water at Ambient Conditions Sci. Rep. 2013, 3 (1074) 1-5
65. Myneni, S.; Luo, Y.; Näslund, L. Å.; Cavalleri, M.; Ojamäe, L.; Ogasawara, H.; Pelmenschikov, A.; Wernet, P.; Väterlein, P.; Heske, C. Spectroscopic Probing of Local Hydrogen-Bonding Structures in Liquid Water J. Phys.: Condens. Matter 2002, 14, L213-L219
66. Cavalleri, M.; Ogasawara, H.; Pettersson, L. G. M.; Nilsson, A. The Interpretation of X-ray Absorption Spectra of Water and Ice Chem. Phys. Lett. 2002, 364, 363-370
67. Iannuzzi, M. X-ray Absorption Spectra of Hexagonal Ice and Liquid Water by All-Electron Gaussian and Augmented Plane Wave Calculations J. Chem. Phys. 2008, 128 (204506) 1-12
68. Smith, J. D.; Cappa, C. D.; Messer, B. M.; Drisdell, W. S.; Cohen, R. C.; Saykally, R. J. Probing the Local Structure of Liquid Water by X-ray Absorption Spectroscopy J. Phys. Chem. B 2006, 110, 20038-20045
69. Heugen, U.; Schwaab, G.; Brüdermann, E.; Heyden, M.; Yu, X.; Leitner, D. M.; Havenith, M. Solute-Induced Retardation of Water Dynamics Probed Directly by Terahertz Spectroscopy Proc. Nat. Acad. Sci. 2006, 103, 12301-12306
70. Stirnemann, G.; Sterpone, F.; Laage, D. Water Hydrogen Bond Dynamics in Aqueous Solutions of Amphiphiles J. Phys. Chem. B 2011, 115, 3254-3262
71. Sarma, R.; Paul, S. The Effect of Aqueous Solutions of Trimethylamine- N -oxide on Pressure Induced Modifications of Hydrophobic Interactions J. Chem. Phys. 2012, 137 (094502) 1-11
72. Vrhovšek, A.; Gereben, O.; Jamnik, A.; Pusztai, L. Hydrogen Bonding and Molecular Aggregates in Liquid Methanol, Ethanol, and 1-Propanol J. Phys. Chem. B 2011, 115, 13473-13488