Quantum mechanical continuum solvation models for ionic liquids

Journal of Physical Chemistry B

Volumn 116, Issue 30, 2012, Pages 9122-9129

  Bernales, Varinia S ^a   Marenich, Aleksandr V ^b   Contreras, Renato ^a   Cramer, Christopher J ^b   Truhlar, Donald G ^b  

^a UNIVERSITY OF CHILE   (Chile)

^b University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FREE ENERGY; QUANTUM THEORY; SOLVATION; SOLVENTS;

AVERAGE VALUES; CONTINUUM SOLVATION MODELS; DESCRIPTORS; ENERGY OF SOLVATION; MACROSCOPIC SOLVENTS; QUANTUM MECHANICAL; QUANTUM MECHANICAL CONTINUUM SOLVATION; SOLVATION FREE ENERGIES; SOLVATION MODELS; SOLVENT PARAMETER;

IONIC LIQUIDS;

EID: 84864780534     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp304365v     Document Type: Article

References (111)

1. Welton, T. Chem. Rev. 1999, 99, 2071-2084
2. Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 997-1000
3. Earle, M. J.; Seddon, K. R. Pure Appl. Chem. 2000, 72, 1391-1398
4. Olivier-Bourbigou, H.; Magna, L. J. Mol. Catal. A: Chem. 2002, 182-183, 419-437
5. Anderson, J. L.; Armstrong, D. W. Anal. Chem. 2003, 75, 4851-4858
6. Marsh, K. N.; Boxall, J. A.; Lichtenthaler, R. Fluid Phase Equilib. 2004, 219, 93-98
7. Garcia, M. T.; Gathergood, N.; Scammells, P. J. Green Chem. 2005, 7, 9-14
8. Yang, Z.; Pan, W. Enzyme Microb. Technol. 2005, 37, 19-28
9. Cocalia, V. A.; Gutowski, K. E.; Rogers, R. D. Coord. Chem. Rev. 2006, 250, 755-764
10. Wang, R. H.; Piekarski, M. M.; Shreeve, J. M. Org. Biomol. Chem. 2006, 4, 1878-1886
11. Pinkert, A.; Marsh, K. N.; Pang, S.; Staiger, M. P. Chem. Rev. 2009, 109, 6712-6728
12. Soukup-Hein, R. J.; Warnke, M. M.; Armstrong, D. W. Annu. Rev. Anal. Chem. 2009, 2, 145-168
13. Nelson, W. M. ACS Symp. Ser. 2002, 818, 30-41
14. Krossing, I.; Slattery, J. M.; Daguenet, C.; Dyson, P. J.; Oleinikova, A.; Weingartner, H. J. Am. Chem. Soc. 2006, 128, 13427-13434
15. Weingaertner, H. Angew. Chem., Int. Ed. 2008, 47, 654-670
16. Giesen, D. J.; Chambers, C. C.; Hawkins, G. D.; Cramer, C. J.; Truhlar, D. G. ACS Symp. Ser. 1998, 677, 285-300
17. Chambers, C. C.; Giesen, D. J.; Hawkins, G. D.; Vaes, W. H. J.; Cramer, C. J.; Truhlar, D. G. In Rational Drug Design; Truhlar, D. G.; Howe, W. J.; Hopfinger, A. J.; Blaney, J. M.; Dammkoehler, R. A., Eds.; Springer: New York, 1999; pp 51-72.
18. Cramer, C. J.; Truhlar, D. G. In Free Energy Calculations in Rational Drug Design; Reddy, M. R.; Erion, M. D., Eds.; Kluwer Academic/Plenum: New York, 2001; pp 63-95.
19. Thompson, J. D.; Cramer, C. J.; Truhlar, D. G. J. Chem. Phys. 2003, 119, 1661-1670
20. Storer, J. W.; Giesen, D. J.; Hawkins, G. D.; Lynch, G. C.; Cramer, C. J.; Truhlar, D. G.; Liotard, D. A. ACS Symp. Ser. 1994, 568, 24-49
21. Chuang, Y.-Y.; Cramer, C. J.; Truhlar, D. G. Int. J. Quantum Chem. 1998, 70, 887-896
22. Cramer, C. J.; Truhlar, D. G. Chem. Rev. 1999, 99, 2161-2200
23. Truhlar, D. G.; Pliego, J. R. In Continuum Solvation Models in Chemical Physics: From Theory to Applications; Mennucci, B.; Cammi, R., Eds.; Wiley: Chichester, U.K., 2008; pp 338-365.
24. Kim, Y.; Mohrig, J. R.; Truhlar, D. G. J. Am. Chem. Soc. 2010, 132, 11071-11082
25. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry; VCH: New York, 1990.
26. Cramer, C. J.; Truhlar, D. G. In Quantitative Treatments of Solute/Solvent Interactions; Politzer, P.; Murray, J. S., Eds.; Elsevier: Amsterdam, The Netherlands, 1994; Vol. 1, pp 9-54.
27. Cramer, C. J. Essentials of Computational Chemistry: Theories and Models, 2 nd ed.; John Wiley & Sons: Chichester, U.K., 2004.
28. Orozco, M.; Luque, F. J. Chem. Rev. 2000, 100, 4187-4225
29. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999-3093
30. Cramer, C. J.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 760-768
31. Mennucci, B. J. Phys. Chem. Lett. 2010, 1, 1666-1674
32. Anderson, J. L.; Ding, J.; Welton, T.; Armstrong, D. W. J. Am. Chem. Soc. 2002, 124, 14247-14254
33. Abraham, M. H.; Zissimos, A. M.; Huddleston, J. G.; Willauer, H. D.; Rogers, R. D.; Acree, W. E. Ind. Eng. Chem. Res. 2003, 42, 413-418
34. Abraham, M. H.; Acree, W. E. Green Chem. 2006, 8, 906-915
35. Acree, W. E.; Abraham, M. H. J. Chem. Technol. Biotechnol. 2006, 81, 1441-1446
36. Mintz, C.; Acree, W. E. Phys. Chem. Liq. 2007, 45, 241-249
37. Sprunger, L. M.; Proctor, A.; Acree, W. E.; Abraham, M. H. Fluid Phase Equilib. 2008, 265, 104-111
38. Bini, R.; Chiappe, C.; Mestre, V. L.; Pomelli, C. S.; Welton, T. Org. Biomol. Chem. 2008, 6, 2522-2529
39. Lei, Z. G.; Chen, B. H.; Li, C. Y.; Liu, H. Chem. Rev. 2008, 108, 1419-1455
40. Hanke, C. G.; Atamas, N. A.; Lynden-Bell, R. M. Green Chem. 2002, 4, 107-111
41. Chaumont, A.; Wipff, G. Phys. Chem. Chem. Phys. 2003, 5, 3481-3488
42. Chaumont, A.; Engler, E.; Wipff, G. Inorg. Chem. 2003, 42, 5348-5356
43. Shim, Y.; Duan, J. S.; Choi, M. Y.; Kim, H. J. J. Chem. Phys. 2003, 119, 6411-6414
44. Chaumont, A.; Wipff, G. J. Phys. Chem. B 2004, 108, 3311-3319
45. Deschamps, J.; Costa Gomes, M. F.; Pádua, A. A. H. ChemPhysChem 2004, 5, 1049-1052
46. Del Popolo, M. G.; Lynden-Bell, R. M.; Kohanoff, J. J. Phys. Chem. B 2005, 109, 5895-5902
47. Del Popolo, M. G.; Kohanoff, J.; Lynden-Bell, R. M. J. Phys. Chem. B 2006, 110, 8798-8803
48. Derecskei, B.; Derecskei-Kovacs, A. Mol. Simul. 2006, 32, 109-115
49. Bhargava, B. L.; Balasubramanian, S. J. Phys. Chem. B 2007, 111, 4477-4487
50. Hardacre, C.; Holbrey, J. D.; Nieuwenhuyzen, M.; Youngs, T. G. A. Acc. Chem. Res. 2007, 40, 1146-1155
51. Köddermann, T.; Paschek, D.; Ludwig, R. ChemPhysChem 2007, 8, 2464-2470
52. Lynden-Bell, R. M.; Del Popolo, M. G.; Youngs, T. G. A.; Kohanoff, J.; Hanke, C. G.; Harper, J. B.; Pinilla, C. C. Acc. Chem. Res. 2007, 40, 1138-1145
53. Padua, A. A. H.; Gomes, M. F.; Lopes, J. Acc. Chem. Res. 2007, 40, 1087-1096
54. Schurhammer, R.; Wipff, G. J. Phys. Chem. B 2007, 111, 4659-4668
55. Moreno, M.; Castiglione, F.; Mele, A.; Pasqui, C.; Raos, G. J. Phys. Chem. B 2008, 112, 7826-7836
56. Bessac, F.; Maseras, F. J. Comput. Chem. 2008, 29, 892-899
57. Chaumont, A.; Wipff, G. J. Phys. Chem. B 2008, 112, 12014-12023
58. Derecskei, B.; Derecskei-Kovacs, A. Mol. Simul. 2008, 34, 1167-1175
59. Shim, Y.; Kim, H. J. J. Phys. Chem. B 2008, 112, 11028-11038
60. Borodin, O. J. Phys. Chem. B 2009, 113, 11463-11478
61. Izgorodina, E. I.; Bernard, U. L.; MacFarlane, D. R. J. Phys. Chem. A 2009, 113, 7064-7072
62. Ficke, L. E.; Brennecke, J. F. J. Phys. Chem. B 2010, 114, 10496-10501
63. Teague, C. M.; Dai, S.; Jiang, D. E. J. Phys. Chem. A 2010, 114, 11761-11767
64. Bruzzone, S.; Malvaldi, M.; Chiappe, C. Phys. Chem. Chem. Phys. 2007, 9, 5576-5581
65. Chiappe, C.; Malvaldi, M.; Pomelli, C. S. J. Chem. Theory Comput. 2009, 6, 179-183
66. Malvaldi, M.; Bruzzone, S.; Chiappe, C.; Gusarov, S.; Kovalenko, A. J. Phys. Chem. B 2009, 113, 3536-3542
67. Diedenhofen, M.; Eckert, F.; Klamt, A. J. Chem. Eng. Data 2003, 48, 475-479
68. Mu, T.; Rarey, J.; Gmehling, J. Ind. Eng. Chem. Res. 2007, 46, 6612-6629
69. Cramer, C. J.; Truhlar, D. G. In Trends and Perspectives in Modern Computational Science; Maroulis, G.; Simos, T. E., Eds.; Brill Academic: Amsterdam, The Netherlands, 2006; Vol. 6, pp 112-140.
70. Cramer, C. J.; Truhlar, D. G. Acc. Chem. Res. 2009, 42, 493-497
71. Giesen, D. J.; Gu, M. Z.; Cramer, C. J.; Truhlar, D. G. J. Org. Chem. 1996, 61, 8720-8721 (erratum 8765 (2000) 5886)
72. Giesen, D. J.; Hawkins, G. D.; Liotard, D. A.; Cramer, C. J.; Truhlar, D. G. Theor. Chem. Acc. 1997, 98, 85-109
73. Hawkins, G. D.; Li, J.; Zhu, T.; Chambers, C. C.; Giesen, D. J.; Liotard, D. A.; Cramer, C. J.; Truhlar, D. G. ACS Symp. Ser. 1998, 712, 201-219
74. Hawkins, G. D.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 1998, 102, 3257-3271
75. Thompson, J. D.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. A 2004, 108, 6532-6542
76. Marenich, A. V.; Olson, R. M.; Kelly, C. P.; Cramer, C. J.; Truhlar, D. G. J. Chem. Theory Comput. 2007, 3, 2011-2033
77. Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2009, 113, 6378-6396 (see eq 16 of this reference for the variation of oxygen radii as a function of solvent σα 2H)
78. Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Chem. Theory Comput. 2009, 5, 2447-2464
79. Ribeiro, R. F.; Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2011, 115, 14556-14562
80. Tomasi, J.; Mennucci, B.; Cances, E. J. Mol. Struct.: THEOCHEM 1999, 464, 211-226
81. Wakai, C.; Oleinikova, A.; Ott, M.; Weingärtner, H. J. Phys. Chem. B 2005, 109, 17028-17030
82. Hu, X.; Zhang, S.; Qu, C.; Zhang, Q.; Lu, L.; Ma, X.; Zhang, X.; Deng, Y. Soft Matter 2011, 7, 5941-5943
83. Martino, W.; de la Mora, J. F.; Yoshida, Y.; Saito, G.; Wilkes, J. Green Chem. 2006, 8, 390-397
84. Hunger, J.; Stoppa, A.; Schrödle, S.; Hefter, G.; Buchner, R. ChemPhysChem 2009, 10, 723-733
85. Daguenet, C.; Dyson, P. J.; Krossing, I.; Oleinikova, A.; Slattery, J.; Wakai, C.; Weingärtner, H. J. Phys. Chem. B 2006, 110, 12682-12688
86. Tariq, M.; Forte, P. A. S.; Gomes, M. F. C.; Lopes, J. N. C.; Rebelo, L. P. N. J. Chem. Thermodyn. 2009, 41, 790-798
87. Huddleston, J. G.; Visser, A. E.; Reichert, W. M.; Willauer, H. D.; Broker, G. A.; Rogers, R. D. Green Chem. 2001, 3, 156-164
88. Singh, T.; Kumar, A. J. Phys. Chem. B 2008, 112, 12968-12972
89. Jaitely, V.; Karatas, A. l.; Florence, A. T. Int. J. Pharm. 2008, 354, 168-173
90. Kamlet, M. J.; Abboud, J. L. M.; Taft, R. W. Prog. Phys. Org. Chem. 1981, 13, 485-630
91. Crowhurst, L.; Mawdsley, P. R.; Perez-Arlandis, J. M.; Salter, P. A.; Welton, T. Phys. Chem. Chem. Phys. 2003, 5, 2790-2794
92. Kamlet, M. J.; Abboud, J. L. M.; Abraham, M. H.; Taft, R. W. J. Org. Chem. 1983, 48, 2877-2887
93. Winget, P.; Dolney, D. M.; Giesen, D. J.; Cramer, C. J.; Truhlar, D. G. Minnesota Solvent Descriptor Database; University of Minnesota: Minneapolis, MN, 2009.
94. Jin, H.; O'Hare, B.; Dong, J.; Arzhantsev, S.; Baker, G. A.; Wishart, J. F.; Benesi, A. J.; Maroncelli, M. J. Phys. Chem. B 2008, 112, 81-92
95. Kobrak, M. N. J. Phys. Chem. B 2007, 111, 4755-4762
96. Kobrak, M. N. Green Chem. 2008, 10, 80-86
97. Tokuda, H.; Tsuzuki, S.; Susan, M.; Hayamizu, K.; Watanabe, M. J. Phys. Chem. B 2006, 110, 19593-19600
98. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Gaussian 09, revision A.02; Gaussian, Inc.: Wallingford, CT, 2010.
99. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215-241
100. Lynch, B. J.; Zhao, Y.; Truhlar, D. G. J. Phys. Chem. A 2003, 107, 1384
101. Li, J.; Cramer, C. J.; Truhlar, D. G. Theor. Chem. Acc. 1998, 99, 192-196
102. Zhao, Y.; Schultz, N. E.; Truhlar, D. G. J. Chem. Theory Comput. 2006, 2, 364-382
103. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
104. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Gaussian 03, revision D.01; Gaussian, Inc.: Wallingford, CT, 2004.
105. Marenich, A. V.; Hawkins, G. D.; Liotard, D. A.; Cramer, C. J.; Truhlar, D. G. GESOL, version 2008; University of Minnesota: Minneapolis, MN, 2008.
106. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100
107. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
108. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
109. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627
110. Paulechka, Y. U.; Zaitsau, D. H.; Kabo, G. J.; Strechan, A. A. Thermochim. Acta 2005, 439, 158-160
111. Physical/Chemical Property Database (PhysProp); SRC Environmental Science Center: Syracuse, NY, 2012, http://www.syrres.com (accessed April 20, 2012).