Elucidation of ionic interactions in the protic ionic liquid solutions by isothermal titration calorimetry

Journal of Physical Chemistry B

Volumn 118, Issue 15, 2014, Pages 4160-4168

  Rai, Gitanjali ^a   Kumar, Anil ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CALORIMETRY; ENTHALPY; ETHYLENE GLYCOL; HYDROGEN BONDS; ISOTHERMS; ORGANIC SOLVENTS; SOLVENTS; TITRATION;

HYDROGEN BONDED NETWORK; ION INTERACTION MODEL; ISOTHERMAL CALORIMETRIC TITRATIONS; ISOTHERMAL TITRATION CALORIMETRY; PARTIAL MOLAR ENTHALPY; PROTIC IONIC LIQUIDS; RELATIVE APPARENT MOLAR ENTHALPY; SOLVENT PROPERTIES;

IONIC LIQUIDS;

EID: 84898987604     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp5019179     Document Type: Article

References (82)

1. Earle, J. M.; Seddon, K. R. Ionic Liquids: Green Solvents for the Future Pure Appl. Chem. 2000, 72, 1391-1398
2. Rogers, R. D.; Seddon, K. R. Ionic Liquids as Green Solvents: Progress and Prospects; ACS Symposium Series; American Chemical Society: Washington, DC, 2003; Vol. 856.
3. Wassercheid, P.; Welton, T. Ionic liquids in Synthesis; Wiley-VCH: Weinheim, Germany, 2003.
4. Seddon, K. R.; Rogers, R. D. Ionic Liquids III A: Fundamentals, Progress, Challenges and Opportunities; ACS Symposium Series; American Chemical Society: Washington, DC, 2005; Vol. 901.
5. Seddon, K. R.; Rogers, R. D. Ionic Liquids III B: Fundamentals, Progress, Challenges and Opportunities; ACS Symposium Series; American Chemical Society: Washington, DC, 2005; Vol. 902.
6. Earle, J. M.; Esperanca, M. S. S. J.; Gilea, A. M.; Lopes, C. N. J.; Rebelo, P. N. L.; Magee, J. W.; Seddon, K. R.; Widegren, J. A. The Distillation and Volatility of Ionic Liquids Nature 2006, 439, 831-834
7. Deetlefs, M.; Seddon, K. R.; Shara, M. Predicting Physical Properties of Ionic Liquids Phys. Chem. Chem. Phys. 2006, 8, 642-649
8. Johnson, K. E. What's an Ionic Liquid? Electrochem. Soc. Interface 2007, 16, 38-41
9. Hee, Z.; Margulis, C. J. Room-Temperature Ionic Liquids: Slow Dynamics, Viscosity, and the Red Edge Effect Acc. Chem. Res. 2007, 40, 1097-1105
10. Hardacre, C.; Holbrey, J. B.; Nieuwenhuyzen, N.; Youngs, T. G. A. Structure and Solvation in Ionic Liquids Acc. Chem. Res. 2007, 40, 1146-1155
11. Saha, S.; Hamaguchi, H. Effect of Water on the Molecular Structure and Arrangement of Nitrile-Functionalized Ionic Liquids J. Phys. Chem. B 2006, 110, 2777-2781
12. Cammarata, L.; Kazarian, S. G.; Salter, P. A.; Welton, T. Molecular States of Water in Room Temperature Ionic Liquids Phys. Chem. Chem. Phys. 2001, 3, 5192-5200
13. Mele, A.; Tran, C. D.; Lacerda, S. H. D. P. The structure of a Room temperature Ionic Liquid With and Without Trace Amounts of Water: The Role of C-H-O and C-H-F Interactions in 1-n-Butyl-3-Methylimidazolium Tetrafluoroborate Angew. Chem., Int. Ed. 2003, 42, 4364-4366
14. 4] J. Solution Chem. 2006, 35, 1337-1346
15. Khupse, N. D.; Kumar, A. Dramatic Change in Viscosities of Pure Ionic Liquids Upon Addition of Molecular Solvents J. Solution Chem. 2009, 38, 589-600
16. Rai, G.; Kumar, A. An Enthalpic Approach to Delineate the Interactions of Cations of Imidazolium-based Ionic Liquids with Molecular Solvents Phys. Chem. Chem. Phys. 2011, 13, 14715-14722
17. Rai, G.; Kumar, A. A Reversal from Endothermic to Exothermic Behavior of Imidazolium-Based Ionic Liquids in Molecular Solvents Chem. Phys. Lett. 2010, 496, 143-147
18. Rai, G.; Kumar, A. Probing Thermal Interaction of Ionic Liquids with Dimethyl Sulfoxide ChemPhysChem 2012, 13, 1927-1933
19. 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
20. Frank, H. S.; Wen, W. Y. Ion-solvent interaction. Structural Aspects of Ion-Solvent Interaction in Aqueous Solutions: A Suggested Picture of Water Structure Discuss. Faraday Soc. 1957, 24, 133-140
21. Kauzmann, W. Some factors in the Interpretation of Protein Denaturation Adv. Protein Chem. 1959, 2, 1-63
22. For example see: Marczak, W.; Vervekin, S. P.; Heintz, A. Enthalpies of Solution of Organic Solutes in the Ionic Liquid 1-methyl-3-ethylimidazolium bis-(trifluoromethyl-sulfonyl) Amide J. Solution Chem. 2003, 32, 519-526
23. 4mim][Gly] at 298.15 K J. Chem. Eng. Data 2009, 54, 2871-2873
24. Waliszewski, D.; Stepniak, I.; Piekarski, H.; Lewandowski, A. Heat Capacities of Ionic Liquids and Their Heats of Solutions in Molecular Liquids Thermochim. Acta 2005, 433, 149-152
25. 4 in Water Thermochim. Acta 2005, 437, 196-197
26. 4] Fluid Phase Equilib. 2006, 247, 80-83
27. ∞ using Modified UNIFAC (Dortmund) Fluid Phase Equilib. 2007, 258, 168-178
28. Fang, D.-W.; Sun, Y.-C.; Wang, Z-W Wang, Solution Enthalpies of Ionic Liquid 1-Hexyl-3-methylimidazolium Chloride J. Chem. Eng. Data 2008, 53, 259-261
29. Guan, G.; Li, L.; Ma, X.-X.; Tong, J.; Fang, D.-W.; Yang, J.-Z. Study on the Enthalpy of Solution and Enthalpy of Dilution for the Ionic Liquid [C3mim][Val] (1-propyl-3-methylimidazolium valine) J. Chem. Thermodyn. 2012, 47, 209-212
30. Hector, T.; Uhlig, L.; Gmehling, J. Prediction of Different Thermodynamic Properties for Systems of Alcohols and Sulfate-based Ionic Liquids Using Modified UNIFAC Fluid Phase Equilib. 2013, 338, 135-140
31. 2] using GLC J. Chem. Thermodyn. 2011, 43, 499-504 and references cited therein
32. Domańska, U. Physico-Chemical Properties and Phase Behaviour of Pyrrolidinium-Based Ionic Liquids Int. J. Mol. Sci. 2010, 11, 1825-1841
33. 4] + water as a case study to model ionic liquid aqueous solutions Green Chem. 2004, 6, 369-381
34. 2O Systems: A Thermodynamic Study J. Phys. Chem. B 2004, 108, 19451-19457
35. Ficke, L. E.; Brennecke, J. F. Interactions of Ionic Liquids and Water J. Phys. Chem. B 2010, 114, 10496-10501
36. Ficke, L. E.; Rodriguez, H.; Brennecke, J. F. Heat Capacities and Excess Enthalpies of 1-Ethyl-3-methylimidazolium-Based Ionic Liquids and Water J. Chem. Eng. Data 2008, 53, 2112-2119
37. Ficke, L. E.; Novak, R. R.; Brennecke, J. F. Thermodynamic and Thermophysical Properties of Ionic Liquid + Water Systems J. Chem. Eng. Data 2010, 55, 4946-4950
38. 2] Pyridinium Ionic Liquids Family and Their Mixtures with the Soft Statistical Associating Fluid Theory Equation of State J. Phys. Chem. B 2012, 116, 9089-9100
39. Paduszynski, K.; Domańska, U. Thermodynamic Modeling of Ionic Liquid Systems: Development and Detailed Overview of Novel Methodology Based on the PC-SAFT J. Phys. Chem. B 2012, 116, 5002-5018
40. Domańska, U.; Zawadzki, M.; Paduszynski, K.; Krolikowski, M. Perturbed-Chain SAFT as a Versatile Tool for Thermodynamic Modeling of Binary Mixtures Containing Isoquinolinium Ionic Liquids J. Phys. Chem. B 2012, 116, 8191-8200
41. Paduszynski, K.; Krolikowski, M.; Domańska, U. Excess Enthalpies of Mixing of Piperidinium Ionic Liquids with Short-Chain Alcohols: Measurements and PC-SAFT Modeling J. Phys. Chem. B 2013, 117, 3884-3891
42. Ohno, H.; Yoshizawa, M. Ion Conductive Characteristics of Ionic Liquids Prepared by Neutralization of Alkylimidazoles Solid State Ionics 2002, 154-155, 303-309
43. Anouti, M.; Jacquemin, J.; Lemordant, D. Transport Properties of Protic Ionic Liquids: Pure and Aqueous Solutions: Effects of Anion and Cation Structure Fluid Phase Equilib. 2010, 297, 13-22
44. Anouti, M.; Caillon-Caravanier, M.; Dridi, Y.; Galiano, H.; Lemordanti, D. Synthesis and Characterization of New Pyrrolidinium Based Protic Ionic Liquids. Good and Superionic Liquids J. Phys. Chem. B 2008, 112, 13335-13343
45. Duan, Z.; Gu, Y.; Zhang, J.; Zhu, L.; Deng, Y. Protic Pyridinium Ionic Liquids: Synthesis, Acidity Determination and their Performances for Acid Catalysis J. Mol. Catal. A: Chem. 2006, 250, 163-168
46. Greaves, T. L.; Drummond, C. J. Protic Ionic Liquids: Properties and Applications Chem. Rev. 2008, 108, 206-237
47. 2O J. Phys. Chem. B 1999, 103, 2981-2983
48. Fumino, K.; Wulf, A.; Ludwig, R. Wasserstoffbrucken in protischen ionischen Flussigkeiten- Ahnlichkeiten mit Wasser Angew. Chem. 2009, 121, 3230-3233
49. Fumino, K.; Wulf, A.; Ludwig, R. Hydrogen Bonding in Protic ionic Liquids: Reminiscent of Water Angew. Chem., Int. Ed. 2009, 48, 3184-3186
50. Wulf, A.; Fumino, K.; Ludwig, R. Spectroscopic Evidence for an Enhanced Anion-Cation Interaction from Hydrogen Bonding in Pure Ionic Liquids Angew. Chem., Int. Ed. 2010, 49, 449-453
51. Padua, A. A. H.; Costa Gomes, M. F.; Lopes, J. N. A. C. Molecular Solutes in Ionic Liquids: A Structural Perspective Acc. Chem. Res. 2007, 40, 1087-1096
52. Huang, M. M.; Weingartner, H. Protic Ionic Liquids with Unusually High Dielectric Permittivities ChemPhysChem 2008, 9, 2172-2173
53. Kruger, M.; Brundermann, E.; Funker, S.; Weingartner, H.; Havenith, M. Communications: Polarity Fluctuations of Protic Ionic Liquid Ethyl Ammonium Nitrate in the Tetrahertz Regime J. Chem. Phys. 2010, 132, 101101-101104
54. Crowhurst, L.; Mawdsley, M. R.; Perez-Arlandis, J. M.; Salter, P. A.; Welton, T. Solvent-solute interactions in ionic liquids Phys. Chem. Chem. Phys. 2003, 5, 2790-2794
55. Bockris, J. O. M.; Reddy, A. K. N. Modern Electrochemistry; Plenum Press: New York, 1970.
56. Pierotti, R. A. A Scaled Particle Theory of Aqueous and Nonaqueous Solutions Chem. Rev. 1976, 76, 717-726
57. 6 Inclusion Crystal Chem. Commun. 2006, 2445-2447
58. Tsuzuki, S.; Mikami, M.; Yamada, S. Origin of Attraction, Magnitude, and Directionality of Interactions in Benzene Complexes with Pyridinium Cations J. Am. Chem. Soc. 2007, 129, 8656-8662
59. Freire, M. G.; Neves, C. M. S. S.; Carvalho, P. J.; Gardas, R. L.; Fernandes, I. M.; Santos, L. M. N. B. F.; Coutinho, J. A. P. Mutual Solubilities of Water and Hydrophobic Ionic Liquids J. Phys. Chem. B 2007, 111, 13082-13089
60. Tanford, C. The Hydrophobic Effect: Formation of Micelles and Biological Membranes; Wiley-Interscience: New York, 1980; p 25.
61. Wu, J.; Prausnitz, J. M. Pairwise- Additive Hydrophobic Effect for Alkanes in Water Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 9512-9515
62. Stillinger, F. H. Structure of Aqueous Solutions of Nonpolar Solutes from the Standpoint of Scaled-Particle Theory J. Solution Chem. 1973, 2, 141-158
63. Pratt, L.; Pohorille, A. Theory of Hydrophobicity: Transient Cavities in Molecular liquids Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 2995-2999
64. Hou, J.; Zhang, Z.; Madsen, L. A. Cation/Anion Associations in Ionic Liquids Modulated by Hydration and Ionic Medium J. Phys. Chem. B 2011, 115, 4576-4582
65. Messikomer, E. E.; Wood, R. H. The Enthalpy of Dilution of Aqueous Sodium Chloride at 298.15 to 373.15 K, Measured with a Flow Calorimeter J. Chem. Thermodyn. 1975, 7, 119-130
66. Mayrath, J. E.; Wood, R. H. Enthalpy of Dilution of Aqueous Sodium Chloride at 348.15 to 472.95 K Measured with a Flow Calorimeter J. Chem. Thermodyn. 1982, 14, 15-26
67. Clarke, E. C.; Glew, D. N. Evaluation of Thermodynamic Functions for Aqueous Sodium Chloride from Equilibrium and Calorimetric Measurements Below 154°C J. Phys. Chem. Ref. Data 1985, 14, 489
68. Marcus, Y. Ion solvation; Wiley-Interscience: Chichester, U.K., 1985.
69. Lankford, J. I.; Criss, C. C. M. Partial molar Heat Capacities of Selected Electrolytes and Benzene in Methanol and Dimethylsulfoxide at 25, 40 and 80°C J. Solution Chem. 1987, 16, 885-906
70. 4] and Water/Dimethyl Sulfoxide J. Phys. Chem. B 2010, 114, 8689-8700
71. Marcus, Y. The Properties of Organic Liquids That are Relevant to Their Use as Solvating Solvents Chem. Soc. Rev. 1993, 22, 409-416
72. Taft, R. W.; Abboud, J. L. M.; Kamlet, M. J.; Abraham, M. H. Linear Solvation Energy Relations J. Solution Chem. 1985, 14, 153-186
73. Harned, H. S.; Owen, B. B. The Physical Chemistry of Electrolyte Solutions; Reinhold Publications: 1950.
74. Pitzer, K. S. Thermodynamics of electrolytes. I. Theoretical Basis and General Equations J. Phys. Chem. 1973, 77, 268-277
75. Pitzer, K. S. Ionic Fluids: Near-Critical and Related Properties J. Phys. Chem. 1995, 99, 13070-13077
76. Pitzer, K. S. In Ion Interaction Approach: Theory and Data Correlation; Pytkowicz, R. M., Ed.; CRC Press: Boca Raton, FL, 1990.
77. Greaves, T. L.; Weerawardena, A.; Fong, C.; Krodkiewska, I.; Drummond, C. J. Protic Ionic Liquids: Solvents with Tunable Phase Behavior and Physicochemical Properties J. Phys. Chem. B 2006, 110, 22479-22487
78. Greaves, T. L.; Weerawardena, A.; Krodkiewska, I.; Drummond, C. J. Protic Ionic Liquids: Physicochemical Properties and Behavior as Amphiphile Self-Assembly Solvents J. Phys. Chem. B 2008, 112, 896-905
79. a from Aqueous Solutions J. Am. Chem. Soc. 2003, 125, 15411-15419
80. Atkin, R.; Warr, G. G. The Smallest Amphiphiles: Nanostructure in Protic Room-Temperature Ionic Liquids with Short Alkyl Groups J. Phys. Chem. B 2008, 112, 4164-4166
81. Greaves, T. L.; Keneddy, D. F.; Mudie, S. T.; Drummond, C. J. Diversity Observed in the Nanostructure of Protic Ionic Liquids J. Phys. Chem. B 2010, 114, 10022-10031
82. Miran, M. S.; Kinoshita, H.; Yasuda, T.; Susan, M. A. B. H.; Watanabe, M. Hydrogen Bonds in Protic Ionic Liquids and Their Correlation with Physicochemical Properties Chem. Commun. 2011, 47, 12676-12678