Deprotonation and oligomerization in photo-, Radiolytically, and electrochemically induced redox reactions in hydrophobic alkylalkylimidazolium ionic liquids

Journal of Physical Chemistry B

Volumn 114, Issue 1, 2010, Pages 368-375

  Shkrob, Ilya A ^a  

^a ARGONNE NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIMERS; EXTRACTION; HYDROPHOBICITY; IONIZATION OF LIQUIDS; MASS SPECTROMETRY; METAL IONS; METAL RECOVERY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLIGOMERIZATION; PHOTODEGRADATION; PHOTOLYSIS; POSITIVE IONS; PROTONS; RADIATION CHEMISTRY; REACTION KINETICS; REDOX REACTIONS;

ALKYLIMIDAZOLIUM; CARBENE CHEMISTRY; CARBENES; COUNTER ANIONS; DICATIONS; EXPERIMENTAL DATA; INDUCED DEGRADATION; ION RADICALS; MASS SPECTRA; NEUTRAL RADICAL; NEUTRAL SPECIES; NMR SPECTRUM; ONE-ELECTRON REDUCTIONS; PROTICITY; RADICAL CATIONS; RADICAL CHEMISTRY; RADICAL PRECURSOR; RADICAL REACTIONS; REACTION SCHEMES; SOLVENT PROPERTIES; TETRAMERS;

IONIC LIQUIDS;

EID: 75649113365     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp9081678     Document Type: Article

References (53)

1. Welton, T. Chem. Rev. 1999, 99, 2071.
2. Earle, M. J.; Seddon, K. P. Pure Appl. Chem. 2000, 72, 1391.
3. Cocalia, V. A.; Gutowski, K. E.; Rogers, R. D. Coord. Chem. Rev. 2006, 250, 755.
4. Dietz, M. L. Sep. Sci. Technol. 2006, 41, 2047.
5. Stepinski, D. C.; Young, B. A.; Jensen, M. P.; Rickert, P. G.; Dzielawa, J. A.; Dilger, A. A.; Rausch, D. J.; Dietz, M. L. Separations for the Nuclear Fuel Cycle in the 21st Century; Lumetta, G., Nash, K. L., Clark, S. B., Friese, J. I., Eds.; ACS Press, 2006; p 233. Jensen, M. P.; Neuefeind, J.; Beitz, J. V.; Skanthakumar, S.; Soderholm, L J. Am. Chem. Soc. 2003, 125, 15466.
6. Luo, H.; Dai, S.; Bonnesen, P. V.; Haverlock, T. J.; Moyer, B. A.; Buchanan, A. C., III Solvent Extr. Ion Exch. 2006, 24, 19.
7. Nikitenko, S. I.; Cannes, C.; Le Naour, C.; Moisy, P.; Trubert, D. Inorg. Chem. 2005, 44, 9497.
8. Chaumont, A.; Wipff, G. Inorg. Chem. 2004, 43, 5891.
9. Visser, A. E.; Jensen, M. P.; Laszak, I.; Nash, K. L.; Choppin, G. R.; Rogers, R. D. Inorg. Chem. 2003, 42, 2197.
10. Dietz, M. L.; Dzielawa, J. A. Chem. Commun. 2001, 2124.
11. Dietz, M. L.; Dzielawa, J. A.; Laszak, I.; Young, B. A.; Jensen, M. P. Green Chem. 2003, 5, 682.
12. Dietz, M. L.; Stepinski, D. C. Green Chem. 2005, 7, 747.
13. Huang, J.-F.; Baker, G. A.; Luo, H.; Hong, K.; Li, Q.-F.; Bjerrum, N. J.; Sheng, D. Green Chem. 2006, 8, 599.
14. Yuan, L.; Peng, J.; Xu, L.; Zhai, M.; Li, J.; Wei, G. J. Chem. Soc., Dalton Trans. 2008, 6358
15. J. Phys. Chem. B 2009, 113, 8948.
16. For the recent overview, see: Matsumoto, H. Electrocheical Aspects of Ionic Liquids; Ohno, H., Ed.; John Wiley & Sons: Hoboken, NJ, 2005; p 35.
17. Wishart, J. F. Energy Environ. Sci. 2009, 2, 956.
18. For a reiew of the current applications, see: MacFarlane, D.; Forsyth, M. The Handbook of Ionic Liquids, Electrochemistry; John-Wiley & Sons: Hoboken, NJ, 2009.
19. Tsuda, T.; Hussey, C. L. Modern Aspects of Electrochemistry; White, R. E., Vayenas, C. G., Eds.; Springer: Munich, 2008.
20. Xiao, L.; Johnson, K. E. J. Electrochem. Soc. 2003, 150, E307.
21. Kroon, M. C.; Bujs, W.; Peters, C. J.; Witkamp, G.-J. Green Chem. 2006, 8, 241.
22. Berton, L.; Nikitenko, S. I.; Bisel, I.; Berthon, C.; Faucon, M.; Saucerotte, B.; Zorz, N.; Moisy, Ph. J. Chem. Soc., Dalton Trans. 2006, 2526. (Observe that the structure given for the m/z = 275.2 mass given in Scheme 2 therein is inconsistent with either this mass or the deprotonation of the dication with m/z = 556.2 shown in Scheme 1 therein. This apparent error has been corrected in section 3 of this study).
23. Kuhl, O. Chem. Soc. Rev. 2007, 36, 592.
24. Herrmann, W. A.; Kocher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162.
25. Adler, R. W. Carbene Chemistry: From Fleeting Intermediates to Powerful Reagents; Bertrand, G., Ed.; Marcel Dekker: New York, 2002; p 153.
26. Shkrob, I. A.; Chemerisov, S. D.; Wishart, J. F. J. Phys. Chem. B 2007, 111, 11786.
27. Takahashi, K.; Sato, T.; Katsumura, Y.; Yang, J.; Kondoh, T.; Yoshida, Y.; et al. Radiat. Phys. Chem. 2008, 77, 1239.
28. Marcinek, A.; Zielonka, J.; Gebicki, J.; Gordon, C. M.; Dunkin, I. R. J. Phys. Chem. A 2001, 105, 9305.
29. Grodkowski, J.; Neta, P. J. Phys. Chem. A 2002, 106, 11130.
30. (a) Chandrasekhar, N.; Endres, F.; Unterreiner, A.-N. Phys. Chem. Chem. Phys. 2006, 8, 3192.
31. Chandrasekhar, N.; Unterreiner, A.-N. Z. Phys. Chem. 2006, 220, 1235.
32. Brands, H.; Chandrasekhar, N.; Unterreiner, A.-N. J. Phys. Chem. B 2007, 111, 4830.
33. Schalk, O.; Brands, H.; Balaban, T. S.; Unterreiner, A.-N. J. Phys. Chem. A 2008, 112, 1719.
34. Chandrasekhar, N.; Schalk, O.; Unterreiner, A.-N. J. Phys. Chem. B 2008, 112, 15718.
35. (b) Wang, Z.; Zhang, L.; Chen, X.; Cukier, R. I.; Bu, Y. J. Phys. Chem. B 2009, 113, 8222.
36. Shkrob, I. A.; Wishart, J. F. J. Phys. Chem. B 2009, 113, 5582.
37. Le Rouzo, G.; Lamouroux, C.; Dauvois, V.; Dannoux, A.; Legand, S.; Durand, D.; Moisy, P.; Moutiers, G. J. Chem. Soc., Dalton Trans. 2009, 6175.
38. Allen, D.; Baston, G.; Bradley, A. E.; Gorman, T.; Haile, A.; Hamblett, I.; Hatter, J. E.; Healey, M. J. F.; Hodgson, B.; Lewin, R.; Lovell, K. V.; Newton, B.; Pitner, W. R.; Rooney, D. W.; Sanders, D.; Seddon, K. R.; Sims, H. E.; Thied, R. C. Green. Chem. 2002, 4, 152.
39. Yan, L.; Peng, J.; Zhai, M.; Li, J.; Wei, G. Radiat. Phys. Chem. 2009, 78, 737.
40. Katoh, R.; Takahashi, K. Radiat. Phys. Chem. 2009, 78, 1126.
41. Tarabek, P.; Liu, S.; Haygarth, K.; Bartels, D. M. Radiat. Phys. Chem. 2009, 78, 168.
42. Elles, C. G.; Shkrob, I. A.; Crowell, R. A.; Landahl, E. C.; Arms, D. A.; Dufresne, E. M. J. Chem. Phys. 2008, 128, 061102. and references therein.
43. Lemal, D. M.; Lovald, R. A.; Kawano, K. I. J. Am. Chem. Soc. 1964, 86, 2518.
44. Chen, Y.-T.; Jordan, F. J. Org. Chem. 1991, 56, 5029.
45. Alder, R. W.; Chaker, L.; Paolini, F. P. J. Chem. Soc., Chem. Commun. 2004, 2172.
46. Qi, M.; Wu, G.; Chen, S.; Liu, Y. Radiat. Res. 2007, 167, 508.
47. (a) Becke, A. D. Phys. Rev.A 1988, 38, 3098.
48. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev.B 1988, 37, 785.
49. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.1;Gaussian, Inc.: Pittsburgh PA, 1998.
50. Ramnial, T.; McKenzie, I.; Gorodetsky, B.; Tsang, E. M. W.; Clyburne, J. A. C. Chem. Commun. 2004, 1054.
51. McKenzie, I.; Brodovitch, J.-C.; Percival, P. W.; Ramnial, T.; Clyburne, J. A. C. J. Am. Chem. Soc. 2003, 125, 11565.
52. Gorodetsky, B.; Ramnial, T.; Branda, N. R.; Clyburne, J. A. C. Chem. Commun. 2004, 1972.
53. Ohno, H. Electrodeposition from Ionic Liquids; Endres, F., Mac-Farlane, D., Abbott, A., Eds.; Wiley-VCH: Weinheim, 2008; p 67.