Prediction of the formation and stabilities of energetic salts and ionic liquids based on ab initio electronic structure calculations

Journal of Physical Chemistry B

Volumn 109, Issue 49, 2005, Pages 23196-23208

  Gutowski, Keith E ^a   Holbrey, John D ^a,b   Rogers, Robin D ^a   Dixon, David A ^a  

^a UNIVERSITY OF ALABAMA   (United States)

^b QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; COMPUTATIONAL METHODS; IONIZATION OF LIQUIDS; PROBABILITY DENSITY FUNCTION; PROTONS; THERMODYNAMICS;

CATION ACIDITIES; GAS-PHASE PROTONS; METHYLATING AGENTS; PROTONATION;

SALTS;

EID: 30544449819     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp053985l     Document Type: Article

References (90)

1. (a) Zhang, M. X.; Eaton, P. E.; Gilardi, R. Angew. Chem., Int. Ed. 2000, 39, 401.
2. (b) Chavez, D. E.; Hiskey, M. A.; Gilardi, R. D. Angew. Chem., Int. Ed. 2000, 39, 1791.
3. (c) Hammerl, A.; Klapötke, T. M.; Warchhold, M. Inorg. Chem. 2001, 40, 3570.
4. Schmidt, E. W. Hydrazine and its Derivatives: Preparation, Properties, Applications, 2nd Ed; John Wiley & Sons: New York, 2001.
5. U.S. Environmental Protection Agency. Integrated Risk Information System (IRIS) on Hydrazine/Hydrazine Sulfate; National Center for Environmental Assessment, Office of Research and Development: Washington, DC, 1999.
6. Drake, G.; Hawkins, T.; Brand, A.; Hall, L.; McKay, M.; Vij, A.; Ismail, I. Propellants, Explos., Pyrotech. 2003, 28, 174.
7. Trohalaki, S.; Pachter, R.; Drake, G. W.; Hawkins, T. Energy Fuels 2005, 19, 279.
8. (a) Ionic Liquids in Synthesis; Wasserscheid, P., Welton, T., Eds.; VCH - Wiley: Weinheim, 2002.
9. (b) Ionic Liquids: Industrial Applications to Green Chemistry; Rogers, R. D., Seddon, K. R., Eds.; ACS Symposium Series 818; American Chemical Society: Washington, DC, 2002.
10. (c) Ionic Liquids as Green Solvents: Progress and Prospects; Rogers, R. D., Seddon, K. R., Eds.; ACS Symposium Series 856; American Chemical Society: Washington, DC, 2003.
11. (d) Ionic Liquids IIIA: Fundamentals, Progress, Challenges, and Opportunities - Properties and Structure; Rogers, R. D., Seddon, K. R., Eds.; ACS Symposium Series 901; American Chemical Society: Washington, DC, 2005.
12. (e) Ionic Liquids IIIB: Fundamentals, Progress, Challenges, and Opportunities - Transformations and Processes; Rogers, R. D., Seddon, K. R., Eds.; ACS Symposium Series 902; American Chemical Society: Washington, DC, 2005.
13. (f) Ionic Liquids in Polymer Systems: Solvents, Additives, and Novel Applications; Brazel, C. S., Rogers, R. D., Eds.; ACS Symposium Series 913; American Chemical Society: Washington, DC, 2005.
14. (a) Welton, T. Chem. Rev. 1999, 99, 2071.
15. (b) Holbrey, J. D.; Seddon, K. R. Clean Prod. Proc. 1999, 1, 223.
16. (c) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772.
17. (d) Sheldon, R. Chem. Commun. 2001, 2399.
18. (e) Gordon, C. M. Appl. Catal., A 2001, 222, 101.
19. (f) Olivier-Bourbigou, H.; Magna, L. J. Mol. Catal., A: Chem. 2002, 182-183, 419.
20. (g) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667.
21. Kaplan, G.; Drake, G.; Tollison, K.; Hall, L.; Hawkins, T. J. Heterocycl. Chem. 2005, 42, 19.
22. Trohalaki, S.; Pachter, R.; Drake, G. W.; Hawkins, T. Energy Fuels 2005, 19, 279.
23. Ogihara, W.; Yoshizawa, M.; Ohto, H. Chem. Lett. 2004, 33, 1022.
24. Katritzky, A. R.; Singh, S.; Kirichemko, K.; Holbrey, J. D.; Smiglak, M. ; Reichert, W. M.; Rogers, R. D. Chem. Commun. 2005, 868.
25. Xue, H.; Gao, Y.; Twamley, B.; Shreeve, J. M. Inorg Chem. 2005, 44, 5068.
26. Xue, H.; Gao, Y.; Twamley, B.; Shreeve, J. M. Chem. Mater. 2005, 17, 191
27. (a) Haake, P.; Bausher, L. P. J. Phys. Chem. 1968, 72, 2213.
28. (b) Haake, P.; Bausher, L. P., Miller, W. B. J. Am. Chem. Soc. 1969, 91, 1113.
29. (c) Aldrich, H. S.; Alworth, W. L.; Clement, N. R. J. Am. Chem. Soc. 1978, 100, 2362.
30. Srinivasan, R.; Feenstra, J. S.; Park, S. T.; Xu, S.; Zewail, A. H. Science 2005, 307, 558.
31. Katritzky, A. R.; Yang, H.; Zhang, D.; Kirichenko, K.; Holbrey, J. D.; Reichert, W. M.; Smiglak, M.; Rogers, R. D. Submitted for publication in New J. Chem.
32. (a) Hilgeman, F. R.; Mouroux, F. Y. N.; Mok, D.; Holan, M. K. J. Chem. Eng. Data 1989, 34, 220.
33. (b) Burns, I. A.; Verrall, R. E. Thermochim. Acta 1974, 9, 277.
34. (c) Domalski, E. S.; Hearing, E. D. J. Phys. Chem. Ref. Data 1996, 1.
35. (d) Wasserscheid, P.; Van Hai, R.; Bösmann, A. Green Chem. 2002, 4, 400.
36. (e) Van Valkenburg, M. E.; Vaughn, R. L.; Williams, M.; Wilkes, J. S. Thermochim. Acta 2005, 425, 181.
37. (a) Jenkins, H. D. B.; Roobottom, H. K.; Passmore, J.; Glasser, L. Inorg. Chem. 1999, 38, 3609.
38. (b) Jenkins, H. D. B.; Tudela, D.; Glasser, L. Inorg. Chem, 2002, 41, 2364.
39. Dixon, D. A.; Gutowski, M. J. Phys. Chem. A 2005, 109, 5129.
40. Dixon, D. A.; Feller, D.; Christe, K. O.; Wilson, W. W.; Vij, A.; Vij, V.; Jenkins, H. D. B.; Olson, R. M.; Gordon, M. S. J. Am. Chem. Soc. 2004, 126, 834.
41. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT. 2004.
42. Aprà, E.; Windus, T. L.; Straatsma, T. P.; Bylaska, E. J.; de Jong, W.; Hirata, S.; Valiev, M.; Hackler, M.; Pollack, L.; Kowalski, K.; Harrison, R.; Dupuis, M.; Smith, D. M. A.; Nieplocha, J.; Tipparaju V.; Krishnan, M.; Auer, A. A.; Brown, E.; Cisneros, G.; Fann, G.; Fruchtl, H.; Garza, J.; Hirao, K.; Kendall, R.; Nichols, J.; Tsemekhman, K.; Wolinski, K.; Anchell, J.; Bernholdt, D.; Borowski, P.; Clark, T.; Clerc, D.; Dachsel, H.; Deegan, M.; Dyall, K.; Elwood, D.; Glendening, E.; Gutowski, M.; Hess, A.; Jaffe, J.; Johnson, B.; Ju, J.; Kobayashi, R.; Kutteh, R.; Lin, Z.; Littlefield, R.; Long, X.; Meng, B.; Nakajima, T.; Niu, S.; Rosing, M.; Sandrone, G.; Stave, M.; Taylor, H.; Thomas, G.; van Lenthe, J.; Wong, A.; Zhang, Z. NWChem, A Computational Chemistry Package for Parallel Computers, Version 4.7; Pacific Northwest National Laboratory: Richland, WA, 2005.
43. Kendall, R. A.; Apra, E.; Bernholdt, D. E.; Bylaska, E. J.; Dupuis, M.; Fann, G. I.; Harrison, R. J.; Ju, J.; Nichols, J. A.; Nieplocha, J.; Straatsma, T. P.; Windus, T. L.; Wong, A. T. Comput. Phys. Commun. 2000, 128, 260-283.
44. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
45. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 1372.
46. (c) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. 1988, 37, 785.
47. Kendall, R. A.; Dunning, T. H., Jr.; Harrison, R. J. J. Chem. Phys. 1992, 96, 6796.
48. Godbout, N.; Salahub, D. R.; Andzelm, J.; Wimmer, E. Can. J. Chem. 1992, 70, 560.
49. (a) Peterson, K. A. J. Chem. Phys. 2003, 119, 11099.
50. (b) Peterson, K. A.; Figgen, D.; Goll, E.; Stoll, H.; Dolg, M. J. Chem. Phys. 2003, 119, 11113.
51. Peterson, K. A.; Woon, D. E.; Dunning, T. H., Jr. J. Chem. Phys. 1994, 100, 7410.
52. Mallouk, T. E.; Rosenthal, G. L.; Muller, G.; Busasco, R.; Bartlett, N. Inorg. Chem. 1984, 23, 3167.
53. Glasser, L.; Jenkins, H. D. B. Thermochim. Acta 2004, 414, 125.
54. Glasser, L. Thermochim. Acta 2004, 421, 87.
55. Alexeev, Y.; Windus, T. L.; Zhan, C.-G.; Dixon, D. A. Int. J. Quantum Chem. 2005, 102, 775.
56. Martin, J. D. D.; Hepburn, J. W. J. Chem. Phys. 1998, 109, 8139.
57. Blondel, C.; Cacciani, P.; Desart, C.; Trainham, R. Phys. Rev. A 1989, 40, 3698.
58. Hanstorp, D.; Gustafsson, M. J. Phys. B 1992, 25, 1773.
59. Wang, X.-B.; Nicholas, J. B.; Wang, L.-S. J. Phys. Chem. A 2000, 104, 504.
60. Viggiano, A. A.; Henchman, M. J.; Dale, F.; Deakyne, C. A.; Paulson, J. F. J. Am. Chem. Soc. 1992, 114, 4299.
61. Koppel, I. A.; Taft, R. W.; Anvia, F.; Zhu, S.-Z.; Hu, L.-Q.; Sung, K.-S.; DesMarteau, D. D.; Yagupolskii. L. M.; Yagupolskii, Y. L.; Ignat'ev, N. V.; Kondratenko, N. V.; Volkonskii, A. Y.; Vlasov, V. M.; Notario, R.; Maria, P.-C. J. Am. Chem. Soc. 1994, 116, 3047.
62. (a) Chase, M. W., Jr. NIST-JANAF Tables, 4th ed. J. Phys. Chem. Ref. Data, Monograph 9, 1998, Suppl. 1.
63. (b) Berkowitz, J.; Ellison, G. B.; Gutman, D. J. Phys. Chem. 1994, 98, 2744.
64. Hunter, E. P.; Lias, S. G. J. Phys. Chem. Ref. Data 1998, 27, 413.
65. (a) Bolte, M.; Lerner, H. W. Acta Crystallogr., Sect. E 2001, 57, m231.
66. (b) Sofina, N.; Peters, E.-M.; Jansen, M. Z. Anorg. Allg. Chem. 2003, 629, 1431.
67. (c) Korus, G.; Jansen, M. Z. Anorg. Allg. Chem. 2001, 627, 1599.
68. (d) Pompetzki, M.; Friese, K.; Jansen, M. Acta Crystallogr., Sect. C 2003, 59, i117.
69. (e) Ganswein, B.; Brauer, G. Z. Anorg. Allg. Chem. 1975, 415, 125.
70. Chen, Z.; Fei, S.; Strauss, H. L. J. Phys. Chem. A 1997, 101, 1640.
71. Jenkins, H. D. B. Lattice Energies. In Handbook of Chemistry and Physics, 79th ed.; Lide, D. R., Ed.; CRC Press: Boca Raton, FL, 1998; Chapter 9, p 1222.
72. Hofmann, D. W. M. Acta Crystallogr., Sect. B 2002, 58, 489.
73. (a) Stephenson, M.; Malanowski, S. Handbook of the Thermodynamics of Organic Compounds; Elsevier: New York, 1987.
74. (b) Timmermans, J.; Mattaar, J. F. Bull. Soc. Chim. Belg. 1921, 30, 213.
75. (c) Howells, R. D.; McCown, J. D. Chem. Rev. 1977, 77, 69.
76. (d) Foeldi, Z. Chem. Ber. 1927, 60, 658.
77. (e) Lide, D. R. CRC Handbook of Chemistry and Physics, Internet Version 2005, http://www.hbcpnetbase.com; CRC Press: Boca Raton, FL, 2005.
78. (f) CRC Handbook of Data on Organic Compounds, 2nd ed.; Weast, R. C., Grasselli, J. G., Eds.; CRC Press: Boca Raton, FL, 1989.
79. (a) Trouton, F. Philos. Mag. 1884, 18, 54.
80. (b) Waser, J. Basic Chemical Thermodynamics; W. A. Benjamins, Inc.: New York, 1966.
81. Westwell, M. S.; Searle, M. S.; Wales, D. J.; Williams, D. H. J. Am. Chem. Soc. 1995, 117, 5013.
82. (a) Arduengo, A. J., III.; Dias, H. V. R.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1992, 114, 5530.
83. (b) Schöfer, S. J.; Kaftzik, N.; Wasserscheid, P.; Kragl, U. Chem. Commun. 2001, 425.
84. (c) Stenzel, O.; Raubenheimer, H. G.; Esterhuysen, C. J. Chem. Soc., Dalton Trans. 2002, 1132.
85. (d) Holbrey, J. D.; Reichert, W. M.; Swatloski, R. P.; Broker, G. A.; Pitner, W. R.; Seddon, K. R.; Rogers, R. D. Green Chem. 2002, 4, 407.
86. (e) Ricciardi, F.; Romanchick, W. A.; Joullié, M. M. J. Polym. Sci. 2003, 21, 1475.
87. (f) Arduengo, A. J., III.; Gamper, S. F.; Tamm, M.; Calabrese, J. C.; Davidson, F.; Craig, H. A. J. Am. Chem. Soc. 1995, 117, 572.
88. (g) Kuhn, N.; Henkel, G.; Kreutzberg, J. Z. Naturforsch. B 1991, 46, 1706.
89. (h) Ngo, H. L.; McEwen, A. B. Proc. - Electrochem. Soc. 1999, 98-15, 683.
90. (i) Chainese, A. R.; Kovacevic, A.; Zeglis, B. M.; Faller, J. W.; Crabtree, R. H. Organometallics 2004, 23, 2461.