Side chain fluorination and anion effect on the structure of 1-butyl-3-methylimidazolium ionic liquids

Journal of Chemical Physics

Volumn 139, Issue 8, 2013, Pages

  Weber, Henry ^a   Hollóczki, Oldamur ^a   Pensado, Alfonso S ^a   Kirchner, Barbara ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ANION EFFECTS; MOLECULAR DYNAMICS SIMULATIONS; MOST LIKELY; SIDE-CHAINS; WEAKLY COORDINATING ANIONS;

FLUORINATION; FLUORINE; HALOGENATION; IONIC LIQUIDS; MOLECULAR DYNAMICS; NEGATIVE IONS; POSITIVE IONS;

CHAINS;

EID: 84903372371     PISSN: 00219606     EISSN: None     Source Type: Journal    
DOI: 10.1063/1.4818540     Document Type: Article

References (123)

1. N. V. Plechkova, and K. R. Seddon, Chem. Soc. Rev. 37, 123-150 (2008). 10.1039/b006677j
2. T. Welton, Chem. Rev. 99, 2071-2083 (1999). 10.1021/cr980032t
3. T. Welton, Coord. Chem. Rev. 248, 2459-2477 (2004). 10.1016/j.ccr.2004. 04.015
4. M. Armand, F. Endres, D. R. MacFarlane, H. Ohno, and B. Scrosati, Nature Mater. 8, 621-629 (2009). 10.1038/nmat2448
5. A. Visser, R. Swatloski, W. Reichert, R. Mayton, S. Sheff, A. Wierzbicki, J. Davis, and R. Rogers, Chem. Commun. 2001, 135-136. 10.1039/b008041l
6. P. Wasserscheid, and W. Keim, Angew. Chem., Int. Ed. 39, 3772-3789 (2000). 10.1002/1521-3773(20001103)39:21<3772::AID-ANIE3772>3.0.CO;2-5
7. J. Davis and K. Forrester, Tetrahedron Lett. 40, 1621-1622 (1999). 10.1016/S0040-4039(99)00025-8
8. A. Wierzbicki and J. H. Davis Jr., in Proceedings of the Symposium on Advances in Solvent Selection and Substitution for Extraction (AIChE, New York, 2000).
9. J. Davis, Chem. Lett. 33, 1072-1077 (2004). 10.1246/cl.2004.1072
10. E. Bates, R. Mayton, I. Ntai, and J. Davis, J. Am. Chem. Soc. 124, 926-927 (2002). 10.1021/ja017593d
11. G. Song, Y. Cai, and Y. Peng, J. Comb. Chem. 7, 561-566 (2005). 10.1021/cc049844v
12. J. H. Hildebrand, J. M. Prausnitz, and R. L. Scott, Regular and Related Solutions (Van Nostrand Reinhold Co., New York, 1970).
13. A. Grosse and G. Cady, Ind. Eng. Chem. 39, 367-374 (1947). 10.1021/ie50447a627
14. C. Tzschucke, C. Markert, W. Bannwarth, S. Roller, A. Hebel, and R. Haag, Angew. Chem., Int. Ed. 41, 3964-4000 (2002). 10.1002/1521-3773(20021104)41: 21<3964::AID-ANIE3964>3.0.CO;2-3
15. I. Horváth and J. Rábai, Science 266, 72-75 (1994). 10.1126/science.266.5182.72
16. D. W. Zhu, Synthesis 1993, 953-954. 10.1055/s-1993-25975
17. I. Klement and P. Knochel, Synlett 1995, 1113-1114. 10.1055/s-1995-5195
18. I. Horváth, G. Kiss, R. Cook, J. Bond, P. Stevens, J. Rabái, and E. Mozeleski, J. Am. Chem. Soc. 120, 3133-3143 (1998). 10.1021/ja9738337
19. V. Chechik and R. Crooks, J. Am. Chem. Soc. 122, 1243-1244 (2000). 10.1021/ja9936870
20. A. Endres and G. Maas, Tetrahedron Lett. 40, 6365-6368 (1999). 10.1016/S0040-4039(99)01332-5
21. M. Cavazzini, G. Pozzi, S. Quici, D. Maillard, and D. Sinou, Chem. Commun. 2001, 1220-1221. 10.1039/b103074b
22. M. Cavazzini, A. Manfredi, F. Montanari, S. Quici, and G. Pozzi, Eur. J. Org. Chem. 2001, 4639-4649. 10.1002/1099-0690(200112)2001:24<4639::AID- EJOC4639>3.0.CO;2-W
23. B. Betzemeier and P. Knochel, Angew. Chem., Int. Ed. Engl. 36, 2623-2624 (1997). 10.1002/anie.199726231
24. S. Schneider and W. Bannwarth, Angew. Chem., Int. Ed. 39, 4142-4145 (2000). 10.1002/1521-3773(20001117)39:22<4142::AID-ANIE4142>3.0.CO;2-0
25. S. Schneider and W. Bannwarth, Helv. Chim. Acta 84, 735-742 (2001). 10.1002/1522-2675(20010321)84:3<735::AID-HLCA735>3.0.CO;2-L
26. C. Markert and W. Bannwarth, Helv. Chim. Acta 85, 1877-1882 (2002). 10.1002/1522-2675(200207)85:7<1877::AID-HLCA1877>3.0.CO;2-5
27. A. Studer, S. Hadida, R. Ferritto, S. Kim, P. Jeger, P. Wipf, and D. Curran, Science 275, 823-826 (1997). 10.1126/science.275.5301.823
28. D. Curran, Synlett 2001, 1488-1496. 10.1055/s-2001-16800
29. R. D. Fowler, J. M. Hamilton, J. S. Kasper, C. E. Weber, W. B. Burford, and H. C. Anderson, Ind. Eng. Chem. 39, 375-378 (1947). 10.1021/ie50447a628
30. N. Kuhn, H. Bohnen, J. Fahl, D. Blaser, and R. Boese, Chem. Ber./Recl. 129, 1579-1586 (1996). 10.1002/cber.19961291228
31. N. Kuhn, G. Weyers, D. Blaser, and R. Boese, Z. Naturforsch. B 56, 1235-1237 (2001).
32. N. N. Yarovenko and M. H. Raksha, Zh. Obshch. Khim. 29, 2159 (1959).
33. L. M. Yagupolskii, N. V. Kondratenko, G. N. Timofeyeva, M. I. Dronkina, and Y. L. Yagupolskii, Zh. Org. Khim. 16, 2508-2513 (1980).
34. L. M. Yagupolskii, T. M. Sokolenko, K. I. Petko, and Y. L. Yagupolskii, J. Fluorine Chem. 126, 667-670 (2005). 10.1016/j.jfluchem.2005.03.003
35. R. Singh, S. Manandhar, and J. Shreeve, Synthesis 2003, 1579-1585. 10.1055/s-2003-40515
36. P. Bonhôte, A. Dias, N. Papageorgiou, K. Kalyanasundaram, and M. Grätzel, Inorg. Chem. 35, 1168-1178 (1996). 10.1021/ic951325x
37. B. R. Caes, J. B. Binder, J. J. Blank, and R. T. Raines, Green Chem. 13, 2719-2722 (2011). 10.1039/c1gc15776k
38. C. Lu, D. VanDerveer, and D. D. DesMarteau, Org. Lett. 10, 5565-5568 (2008). 10.1021/ol802399z
39. T. Merrigan, E. Bates, S. Dorman, and J. Davis, Chem. Commun. 2000, 2051-2052. 10.1039/b005418f
40. J. Crosthwaite, M. Muldoon, J. Dixon, J. Anderson, and J. Brennecke, J. Chem. Thermodyn. 37, 559-568 (2005). 10.1016/j.jct.2005.03.013
41. J. E. Bara, C. J. Gabriel, T. K. Carlisle, D. E. Camper, A. Finotello, D. L. Gin, and R. D. Noble, Chem. Eng. J. 147, 43-50 (2009). 10.1016/j.cej.2008. 11.021
42. D. Almantariotis, T. Gefflaut, A. A. H. Pádua, J. Y. Coxam, and M. F. Costa Gomes, J. Phys. Chem. B 114, 3608-3617 (2010). 10.1021/jp912176n
43. M. Döbbelin, R. Marcilla, C. Tollan, J. A. Pomposo, J.-R. Sarasua, and D. Mecerreyes, J. Mater. Chem. 18, 5354-5358 (2008). 10.1039/b808723g
44. R. J. LeSuer and W. E. Geiger, J. Electroanal. Chem. 594, 20-26 (2006). 10.1016/j.jelechem.2006.05.016
45. D. Ondo, M. Tkadlecová, V. Dohnal, J. Rak, J. Kvíč ala, J. K. Lehmann, A. Heintz, and N. Ignatiev, J. Phys. Chem. B 115, 10285-10297 (2011). 10.1021/jp205039g
46. G. D. Smith, O. Borodin, J. J. Magda, R. H. Boyd, Y. Wang, J. E. Bara, S. Miller, D. L. Gin, and R. D. Noble, Phys. Chem. Chem. Phys. 12, 7064-7076 (2010). 10.1039/c001387k
47. H. Feng, J. Zhou, and Y. Qian, J. Chem. Phys. 135, 144501 (2011). 10.1063/1.3641486
48. J. J. Hettige, H. K. Kashyap, H. V. R. Annapureddy, and C. J. Margulis, J. Phys. Chem. Lett. 4, 105-110 (2013). 10.1021/jz301866f
49. S. Yeganegi, A. Soltanabadi, and D. Farmanzadeh, J. Phys. Chem. B 116, 11517-11526 (2012). 10.1021/jp3059933
50. E. Bodo, L. Gontrani, A. Triolo, and R. Caminiti, J. Phys. Chem. Lett. 1, 1095-1100 (2010). 10.1021/jz100146r
51. E. Bodo, L. Gontrani, R. Caminiti, N. V. Plechkova, K. R. Seddon, and A. Triolo, J. Phys. Chem. B 114, 16398-16407 (2010). 10.1021/jp1093299
52. W. Pan, Y. Qi, R. Wang, Z. Han, D. Zhang, and J. Zhan, Chemosphere 91, 157-164 (2013). 10.1016/j.chemosphere.2012.12.021
53. Y. Zhao, X. Liu, J. Wang, and S. Zhang, ChemPhysChem 13, 3126-3133 (2012). 10.1002/cphc.201200286
54. E. D. Hazelbaker, S. Budhathoki, A. Katihar, J. K. Shah, E. J. Maginn, and S. Vasenkov, J. Phys. Chem. B 116, 9141-9151 (2012). 10.1021/jp304528d
55. H. Liu, E. Maginn, A. E. Visser, N. J. Bridges, and E. B. Fox, Ind. Eng. Chem. Res. 51, 7242-7254 (2012). 10.1021/ie300222a
56. K. Shimizu, M. Tariq, L. P. N. Rebelo, and J. N. Canongia Lopes, J. Mol. Liq. 153, 52-56 (2010); 10.1016/j.molliq.2009.07.012
57. in Proceedings of the Annual Meeting of the European-Molecular-Liquid- Group (EMLG), Fund Calouste Gulbenkian, Lisbon, Portugal, 31 August-4 September 2008.
58. M. J. Muldoon, S. N. V. K. Aki, J. L. Anderson, J. K. Dixon, and J. F. Brennecke, J. Phys. Chem. B 111, 9001-9009 (2007). 10.1021/jp071897q
59. M. Gonzalez-Miquel, J. Palomar, S. Omar, and F. Rodriguez, Ind. Eng. Chem. Res. 50, 5739-5748 (2011). 10.1021/ie102450x
60. A. Martín and M. Dolores Bermejo, J. Supercrit. Fluids 55, 852-859 (2010). 10.1016/j.supflu.2010.10.012
61. J. L. Anthony, J. L. Anderson, E. J. Maginn, and J. F. Brennecke, J. Phys. Chem. B 109, 6366-6374 (2005). 10.1021/jp046404l
62. S. Stolte, J. Arning, U. Bottin-Weber, M. Matzke, F. Stock, K. Thiele, M. Uerdingen, U. Welz-Biermann, B. Jastorff, and J. Ranke, Green Chem. 8, 621-629 (2006). 10.1039/b602161a
63. D. Xiao, J. R. Rajian, A. Cady, S. Li, R. A. Bartsch, and E. L. Quitevis, J. Phys. Chem. B 111, 4669-4677 (2007). 10.1021/jp066481b
64. S. Plimpton, J. Comput. Phys. 117, 1-19 (1995); See http://lammps.sandia. gov for detailed information about the LAMMPS program package. 10.1006/jcph.1995.1039
65. W. D. Cornell, P. Cieplak, C. I. Bayly, I. R. Gould, K. M. Merz, D. M. Ferguson, D. C. Spellmeyer, T. Fox, J. W. Caldwell, and P. A. Kollman, J. Am. Chem. Soc. 117, 5179-5197 (1995). 10.1021/ja00124a002
66. R. W. Hockney and J. W. Eastwood, Computer Simulation Using Particles (Adam Hilger, 1989).
67. M. Deserno and C. Holm, J. Chem. Phys. 109, 7694-7701 (1998). 10.1063/1.477415
68. J. N. Canongia Lopes, J. Deschamps, and A. Pádua, J. Phys. Chem. B 108, 2038-2047 (2004). 10.1021/jp0362133
69. J. N. Canongia Lopes and A. Pádua, J. Phys. Chem. B 108, 16893-16898 (2004). 10.1021/jp0476545
70. J. N. Canongia Lopes and A. Pádua, J. Phys. Chem. B 110, 19586-19592 (2006). 10.1021/jp063901o
71. K. Shimizu, D. Almantariotis, M. F. Costa Gomes, A. A. H. Pádua, and J. N. Canongia Lopes, J. Phys. Chem. B 114, 3592-3600 (2010). 10.1021/jp9120468
72. W. L. Jorgensen, D. S. Maxwell, and J. Tirado-Rives, J. Am. Chem. Soc. 118, 11225-11236 (1996). 10.1021/ja9621760
73. Z. Y. Yu, M. P. Jacobson, J. Josovitz, C. S. Rapp, and R. A. Friesner, J. Phys. Chem. B 108, 6643-6654 (2004). 10.1021/jp037821l
74. J. Wang, R. M. Wolf, J. W. Caldwell, P. A. Kollman, and D. A. Case, J. Comp. Chem. 25, 1157-1174 (2004). 10.1002/jcc.20035
75. U. C. Singh and P. A. Kollman, J. Comput. Chem. 5, 129 (1984). 10.1002/jcc.540050204
76. P. Hohenberg and W. Kohn, Phys. Rev. B 136, B864 (1964). 10.1103/PhysRev.136.B864
77. W. Kohn and L. Sham, Phys. Rev. 140, A1133 (1965). 10.1103/PhysRev.140. A1133
78. A. Becke, Phys. Rev. A 38, 3098-3100 (1988). 10.1103/PhysRevA.38.3098
79. C. Lee, W. Yang, and R. Parr, Phys. Rev. B 37, 785-789 (1988). 10.1103/PhysRevB.37.785
80. J. VandeVondele and J. Hutter, J. Chem. Phys. 127, 114105 (2007). 10.1063/1.2770708
81. S. Goedecker, M. Teter, and J. Hutter, Phys. Rev. B 54, 1703-1710 (1996). 10.1103/PhysRevB.54.1703
82. C. Hartwigsen, S. Goedecker, and J. Hutter, Phys. Rev. B 58, 3641-3662 (1998). 10.1103/PhysRevB.58.3641
83. S. Grimme, J. Comput. Chem. 27, 1787-1799 (2006). 10.1002/jcc.20495
84. W. Hehre, R. Ditchfield, and J. Pople, J. Chem. Phys. 56, 2257 (1972). 10.1063/1.1677527
85. M. Francl, W. Pietro, W. Hehre, J. Binkley, M. Gordon, D. Defrees, and J. Pople, J. Chem. Phys. 77, 3654-3665 (1982). 10.1063/1.444267
86. J. VandeVondele, M. Krack, F. Mohamed, M. Parrinello, T. Chassaing, and J. Hutter, Comput. Phys. Commun. 167, 103-128 (2005). 10.1016/j.cpc.2004.12.014
87. See http://cp2k.berlios.de/ for information on the CP2K developers group, 2004.
88. See supplementary material at http://dx.doi.org/10.1063/1.4818540 E-JCPSA6-139-043332 for general information, different radial distribution, and combined distribution functions for all investigated systems.
89. S. Nosé, J. Chem. Phys. 81, 511-519 (1984). 10.1063/1.447334
90. S. Nosé, Mol. Phys. 52, 255-268 (1984). 10.1080/00268978400101201
91. G. Martyna, M. Klein, and M. Tuckerman, J. Chem. Phys. 97, 2635-2643 (1992). 10.1063/1.463940
92. G. F. Voronoi, J. Reine Angew. Math. 134, 198-287 (1908). 10.1515/crll.1908.134.198
93. J. M. S. S. Esperança, J. N. Canongia Lopes, M. Tariq, L. M. N. B. F. Santos, J. W. Magee, and L. P. N. Rebelo, J. Chem. Eng. Data 55, 3-12 (2010). 10.1021/je900458w
94. O. Hollóczki, D. Gerhard, K. Massone, L. Szarvas, B. Németh, T. Veszprémi, and L. Nyulászi, New J. Chem. 34, 3004-3009 (2010). 10.1039/c0nj00380h
95. S. P. Verevkin, D. H. Zaitsau, V. N. Emel'yanenko, and A. Heintz, J. Phys. Chem. B 115, 12889-12895 (2011). 10.1021/jp207397v
96. M. Brehm and B. Kirchner, J. Chem. Inf. Model. 51, 2007-2023 (2011). 10.1021/ci200217w
97. J. Huddleston, A. Visser, W. Reichert, H. Willauer, G. Broker, and R. Rogers, Green Chem. 3, 156-164 (2001). 10.1039/b103275p
98. M. B. Shiflett, D. J. Kasprzak, C. P. Junk, and A. Yokozeki, J. Chem. Thermodyn. 40, 25-31 (2008). 10.1016/j.jct.2007.06.003
99. H. Tokuda, S. Tsuzuki, M. A. B. H. Susan, K. Hayamizu, and M. Watanabe, J. Phys. Chem. B 110, 19593-19600 (2006). 10.1021/jp064159v
100. H. Tokuda, K. Hayamizu, K. Ishii, M. Abu Bin Hasan Susan, and M. Watanabe, J. Phys. Chem. B 108, 16593-16600 (2004). 10.1021/jp047480r
101. J. Jacquemin, P. Husson, V. Mayer, and I. Cibulka, J. Chem. Eng. Data 52, 2204-2211 (2007). 10.1021/je700224j
102. See http://ilthermo.boulder.nist.gov for Ionic Liquids Database-ILThermo.
103. M. Connolly, J. Am. Chem. Soc. 107, 1118-1124 (1985). 10.1021/ja00291a006
104. O. Borodin, J. Phys. Chem. B 113, 11463-11478 (2009). 10.1021/jp905220k
105. S. P. Verevkin, D. H. Zaitsau, V. N. Emel'yanenko, A. V. Yermalayeu, C. Schick, H. Liu, E. J. Maginn, S. Bulut, I. Krossing, and R. Kalb, J. Phys. Chem. B 117, 6473-6486 (2013). 10.1021/jp311429r
106. H. Luo, G. A. Baker, and S. Dai, J. Phys. Chem. B 112, 10077-10081 (2008). 10.1021/jp805340f
107. D. H. Zaitsau, S. P. Verevkin, V. N. Emel'yanenko, and A. Heintz, ChemPhysChem 12, 3609-3613 (2011). 10.1002/cphc.201100618
108. P. A. Hunt, B. Kirchner, and T. Welton, Chem.-Eur. J. 12, 6762-6775 (2006). 10.1002/chem.200600103
109. M. Brehm, H. Weber, A. S. Pensado, A. Stark, and B. Kirchner, Phys. Chem. Chem. Phys. 14, 5030-5044 (2012). 10.1039/c2cp23983c
110. F. Malberg, A. S. Pensado, and B. Kirchner, Phys. Chem. Chem. Phys. 14, 12079-12082 (2012). 10.1039/c2cp41878a
111. A. S. Pensado, M. Brehm, J. Thar, A. P. Seitsonen, and B. Kirchner, ChemPhysChem 13, 1845-1853 (2012). 10.1002/cphc.201100917
112. L. L. Burger and G. H. Cady, J. Am. Chem. Soc. 73, 4243-4246 (1951). 10.1021/ja01153a061
113. A. Mele, G. Romanó, M. Giannone, E. Ragg, G. Fronza, G. Raos, and V. Marcon, Angew. Chem., Int. Ed. 45, 1123-1126 (2006). 10.1002/anie.200503745
114. M. Kohagen, M. Brehm, J. Thar, W. Zhao, F. Mueller-Plathe, and B. Kirchner, J. Phys. Chem. B 115, 693-702 (2011). 10.1021/jp109612k
115. J. Thar, M. Brehm, A. P. Seitsonen, and B. Kirchner, J. Phys. Chem. B 113, 15129-15132 (2009). 10.1021/jp908110j
116. Y. Wang and G. Voth, J. Am. Chem. Soc. 127, 12192-12193 (2005). 10.1021/ja053796g
117. J. N. Canongia Lopes and A. A. H. Pádua, J. Phys. Chem. B 110, 3330-3335 (2006). 10.1021/jp056006y
118. S. B. C. Lehmann, M. Roatsch, M. Schoppke, and B. Kirchner, Phys. Chem. Chem. Phys. 12, 7473-7486 (2010). 10.1039/b921246a
119. I. Skarmoutsos, D. Dellis, R. P. Matthews, T. Welton, and P. A. Hunt, J. Phys. Chem. B 116, 4921-4933 (2012). 10.1021/jp209485y
120. M. Kohagen, M. Brehm, Y. Lingscheid, R. Giernoth, J. Sangoro, F. Kremer, S. Naumov, C. Iacob, J. Kaerger, R. Valiullin, and B. Kirchner, J. Phys. Chem. B 115, 15280-15288 (2011). 10.1021/jp206974h
121. P. A. Hunt, J. Phys. Chem. B 111, 4844-4853 (2007). 10.1021/jp067182p
122. O. Hollóczki, Z. Kelemen, L. Könczöl, D. Szieberth, L. Nyulászi, A. Stark, and B. Kirchner, ChemPhysChem 14, 315-320 (2013). 10.1002/cphc.201200970
123. K. Shimizu, M. Tariq, M. F. Costa Gomes, L. P. N. Rebelo, and J. N. Canongia Lopes, J. Phys. Chem. B 114, 5831-5834 (2010). 10.1021/jp101910c