Radiation stability of cations in ionic liquids. 3. Guanidinium cations

Journal of Physical Chemistry B

Volumn 117, Issue 46, 2013, Pages 14400-14407

  Shkrob, Ilya A ^a   Marin, Timothy W ^a,b   Bell, Jason R ^c   Luo, Huimin ^c   Dai, Sheng ^c  

^a ARGONNE NATIONAL LABORATORY   (United States)

^b BENEDICTINE UNIVERSITY   (United States)

^c OAK RIDGE NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL MECHANISM; CHEMICAL PATHWAYS; ELECTRON PARAMAGNETIC RESONANCE SPECTROSCOPY; GUANIDINIUM CATIONS; METAL ION SEPARATION; RADIATION STABILITY; RADIONUCLIDE SEPARATIONS; ROOM TEMPERATURE IONIC LIQUIDS;

ELECTRON SPIN RESONANCE SPECTROSCOPY; IONIC LIQUIDS; MASS SPECTROMETRY; METAL IONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RADIATION CHEMISTRY; RADIATION DAMAGE; RADIOISOTOPES; RADIOLYSIS; SEPARATION;

POSITIVE IONS;

EID: 84888629623     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp408253y     Document Type: Article

References (44)

1. Xie, H.; Zhang, S.; Duan, H. An Ionic Liquid Based on a Cyclic Guanidinium Cation Is an Efficient Medium for the Selective Oxidation of Benzyl Alcohols Tetrahedron Lett. 2004, 45, 2013-2015
2. Wang, P.; Zakeeruddin, S. M.; Graetzel, M.; Kantlehner, W.; Mezger, J.; Stoyanov, E. V.; Scherr, O. Novel Room Temperature Ionic Liquids of Hexaalkyl Substituted Guanidinium Salts for Dye-Sensitized Solar Cells Appl. Phys. A: Mater. Sci. Process. 2004, 79, 73-77
3. Gao, Y.; Arritt, S. W.; Twamley, B.; Shreeve, J. M. Guanidinium-Based Ionic Liquids Inorg. Chem. 2005, 44, 1704-1712
4. Kulkarni, P. S.; Branco, L. C.; Crespo, J. G.; Nunes, M. C.; Raymundo, A.; Afonso, C. A. M. Comparison of Physicochemical Properties of New Ionic Liquids Based on Imidazolium, Quaternary Ammonium, and Guanidinium Cations Chem.-Eur. J. 2007, 2007, 8478-8488
5. Bogdanov, M. G.; Petkova, D.; Hristeva, S.; Svinyarov, I.; Kantlehnerb, W. New Guanidinium-Based Room-Temperature Ionic Liquids. Substituent and Anion Effect on Density and Solubility in Water Z. Naturforsch. 2010, 65b, 37-48
6. 2 Capture by Guanidinium-Based Ionic Liquids: A Theoretical Study J. Phys. Chem. B 2010, 115, 3466-3477
7. Rad-Moghadam, K.; Youseftabar-Miri, L. Tetramethylguanidinium Triflate: An Efficient Catalyst Solvent for the Convergent Synthesis of Fused Spiro[1,4-Dihydropyridine-Oxindole] Compounds J. Fluorine Chem. 2012, 135, 213-219
8. Li, S.; Lin, Y.; Xie, H.; Zhang, S.; Xu, J. Brønsted Guanidine Acid-Base Ionic Liquids: Novel Reaction Media for the Palladium-Catalyzed Heck Reaction Org. Lett. 2006, 8, 391-394
9. Wang, W.; Shao, L.; Cheng, W.; Yang, J.; He, M. Brønsted Acidic Ionic Liquids as Novel Catalysts for Prins Reaction Catal. Commun. 2008, 9, 337-341
10. 2 by Ionic Liquids Chem. Commun. 2006, 4027-4029
11. Fang, S.; L., Y.; J., W.; Zhang, H.; K., T.; Kamijima, K. Guanidinium-Based Ionic Liquids as New Electrolytes for Lithium Battery J. Power Sources 2009, 191, 619-622
12. 4 Battery Performance with a Guanidinium-Based Ionic Liquid as the Electrolyte Chin. Sci. Bull. 2011, 56, 2906-2910
13. Welton, T. Room-Temperature Ionic Liquids. Solvents for Synthesis and Catalysis Chem. Rev. 1999, 99, 2071-2083
14. Hallett, J. P.; Welton, T. Room-Temperature Ionic Liquids: Solvents for Synthesis and Catalysis. 2 Chem. Rev. 2011, 111, 3508-3576
15. Plechkova, N. V.; Seddon, K. R. Applications of Ionic Liquids in the Chemical Industry Chem. Soc. Rev. 2008, 37, 123-150
16. Smiglak, M.; Metlen, A.; Rogers, R. D. The Second Evolution of Ionic Liquids: From Solvents and Separations to Advanced Materials-Energetic Examples from the Ionic Liquid Cookbook Acc. Chem. Res. 2007, 1182-1192
17. Sun, X. Q.; Luo, H. M.; Dai, S. Ionic Liquids-Based Extraction: A Promising Strategy for the Advanced Nuclear Fuel Cycle Chem. Rev. 2012, 112, 2100-2128
18. 6] During Extraction of Strontium Ions Dalton Trans. 2008, 6358-6360
19. 2N] under Gamma Irradiation Dalton Trans. 2008, 924-931
20. Tarabek, P.; Shengyan, L.; Haygarth, K.; Bartels, D. M. Hydrogen Gas Yields in Irradiated Room-Temperature Ionic Liquids Radiat. Phys. Chem. 2009, 78, 168-172
21. Wishart, J. F.; Shkrob, I. A. The Radiation Chemistry of Ionic Liquids and Its Implications for Their Use in Nuclear Fuel Processing; American Chemical Society: Washington, DC, 2009; pp 119-134.
22. Le Rouzo, G.; Lamouroux, C.; Dauvois, V.; Dannoux, A.; Legand, S.; Durand, D.; Moisy, P.; G., M. Anion Effect on Radiochemical Stability of Room-Temperature Ionic Liquids under Gamma Irradiation Dalton Trans. 2009, 6175-6184
23. Berthon, L.; Chabronnel, M.-C. Radiolysis of Solvents Used in Nuclear Fuel Reprocessing. In Ion Exchange and Solvent Extraction, A Series of Advances; Moyer, B. A., Ed.; CRC Press: Boca Raton, FL, 2010; Vol. 19, pp 429-513.
24. Dhiman, S. B.; Goff, G. S.; Runde, W.; LaVerne, J. A. Hydrogen Production in Aromatic and Aliphatic Ionic Liquids J. Phys. Chem. B 2013, 117, 6782-6788
25. Wishart, J. F. Ionic Liquid Radiation Chemistry. In Ionic Liquids: Coiled for Action; Seddon, K. R.; Rogers, R. D., Eds.; Wiley, Ltd.: Chichester, U.K., 2013; in press.
26. Shkrob, I. A.; Marin, T. W.; Chemerisov, S. D.; Hatcher, J. L.; Wishart, J. F. Radiation Induced Redox Reactions and Fragmentation of Constituent Ions in Ionic Liquids. 2. Imidazolium Cations J. Phys. Chem. B 2011, 115, 3889-3902
27. Shkrob, I. A.; Wishart, J. F. Free Radical Chemistry in Room-Temperature Ionic Liquids. In Encyclopedia of Radicals in Chemistry, Biology and Materials; Chatgilialoglu, C.; Studer, A., Eds.; John Wiley & Sons, Ltd.: Chichester, U.K., 2012; pp 433-448.
28. 2N Dalton Trans. 2006, 2526-2534
29. Wishart, J. F. Ionic Liquids and Ionizing Radiation: Reactivity of Highly Energetic Species J. Phys. Chem. Lett. 2010, 1, 3225-3231
30. MacFarlane, D. R.; Forsyth, S. A.; Golding, J.; Deacon, G. B. Ionic Liquids Based on Imidazolium, Ammonium and Pyrrolidinium Salts of the Dicyanamide Anion Green Chem. 2002, 4, 444-448
31. Shkrob, I. A.; Chemerisov, S. D.; Wishart, J. F. The Initial Stages of Radiation Damage in Ionic Liquids and Ionic Liquid-Based Extraction Systems J. Phys. Chem. B 2007, 111, 11786-11793
32. Shkrob, I. A.; Wishart, J. F. Charge Trapping in Imidazolium Ionic Liquids J. Phys. Chem. B 2009, 113, 5582-5592
33. Shkrob, I. A.; Marin, T. W.; Wishart, J. F. Ionic Liquids Based on Polynitrile Anions: Hydrophobicity, Low Proton Affinity, and High Radiolytic Resistance Combined J. Phys. Chem. B 2013, 117, 7084-7094
34. Shkrob, I. A.; Marin, T. W.; Wishart, J. F. Radiation Stability of Cations in Ionic Liquids. 2. Improved Radiation Resistance through Charge Delocalization in 1-Benzylpyridinium. J. Phys. Chem. B 2013, DOI: 10.1021/jp408242b.
35. Shkrob, I. A.; Marin, T. W.; Luo, H.; Dai, S. Radiation Stability of Cations in Ionic Liquids. 1. Alkyl and Benzyl Derivatives of 5-Membered Ring Heterocycles. J. Phys. Chem. B 2013, DOI: 10.1021/jp4082432.
36. Becke, A. D. Density-Functional Exchange-Energy Approximation with Correct Asymptotic Behavior Phys. Rev. A 1988, 38, 3098-3100
37. Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron Density Phys. Rev. B 1988, 37, 785-789
38. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, V. G.; Montgomery, J. A., Jr.; Vreven, K. N.; Kudin, J. C.; Burant, J. C. Gaussian 03, rev. C.02; Gaussian, Inc.: Wallingford, CT, 2004.
39. 3, and Dialkylphosphoric Acids in Room-Temperature Ionic Liquids J. Phys. Chem. B 2011, 115, 10927-10942
40. Shkrob, I. A.; Marin, T. W.; Chemerisov, S. D.; Wishart, J. F. Radiation-Induced Redox Reactions and Fragmentation of Constituent Ions in Ionic Liquids. I. Anions J. Phys. Chem. B 2011, 115, 3872-3888
41. Shkrob, I. A.; Marin, T. W.; Crowell, R. A.; Wishart, J. F. Photo- and Radiation- Chemistry of Halide Anions in Ionic Liquids J. Phys. Chem. A 2013, 117, 5742-5756
42. Shaffer, S. A.; Turecek, F.; Cerny, R. L. The (Dimethylamino)Methyl Radical. A Neutralization-Reionization and Ab Initio Study J. Am. Chem. Soc. 1993, 115, 12117-12124
43. Hao, C.; Seymour, J. L.; Turecek, F. Electron Super-Rich Radicals in the Gas Phase. A Neutralization-Reionization Mass Spectrometric and Ab Initio/RRKM Study of Diaminohydroxymethyl and Triaminomethyl Radicals J. Phys. Chem. A 2007, 111, 8829-8843
44. Olah, G. A.; Burrichter, A.; Rasul, G.; Hachoumy, M.; Prakash, G. K. S. 1h, 13c, 15n Nmr and Ab Initio/IGLO/GIAO-MP2 Study of Mono-, Di-, Tri-, and Tetraprotonated Guanidine J. Am. Chem. Soc. 1997, 119, 12929-12933