Vapors from ionic liquids: Reconciling simulations with mass spectrometric data

Journal of Physical Chemistry Letters

Volumn 3, Issue 23, 2012, Pages 3435-3441

  Neto, Brenno A D ^a   Meurer, Eduardo C ^b   Galaverna, Renan ^b   Bythell, Benjamin J ^c   Dupont, Jairton ^d   Graham Cooks, R ^e   Eberlin, Marcos N ^b  

^a UNIVERSITY OF BRASILIA   (Brazil)

^b UNIVERSITY OF CAMPINAS   (Brazil)

^c FLORIDA STATE UNIVERSITY   (United States)

^d FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

^e PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

APROTIC; DFT CALCULATION; GAS-PHASE DISSOCIATION; INTERNAL ENERGIES; ION PAIRS; LASER-INDUCED ACOUSTIC DESORPTIONS; MASS SPECTROMETRIC DATA; THEORETICAL SIMULATION;

DENSITY FUNCTIONAL THEORY; DISSOCIATION; DISTILLATION; IONS; MASS SPECTROMETERS; THERMAL DESORPTION;

IONIC LIQUIDS;

EID: 84870800796     PISSN: None     EISSN: 19487185     Source Type: Journal    
DOI: 10.1021/jz301608c     Document Type: Article

References (45)

1. Welton, T. Room-Temperature Ionic Liquids. Solvents for Synthesis and Catalysis Chem. Rev. 1999, 99, 2071-2083
2. Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Ionic Liquid (Molten Salt) Phase Organometallic Catalysis Chem. Rev. 2002, 102, 3667-3691
3. Seddon, K. R. Ionic Liquids: A Taste of the Future Nat. Mater. 2003, 2, 363-365
4. Rogers, R. D.; Seddon, K. R. Ionic Liquids - Solvents of the Future? Science 2003, 302, 792-793
5. Plechkova, N. V.; Seddon, K. R. Applications of Ionic Liquids in the Chemical Industry Chem. Soc. Rev. 2008, 37, 123-150
6. Hallett, J. P.; Welton, T. Room-Temperature Ionic Liquids: Solvents for Synthesis and Catalysis Chem. Rev. 2011, 111, 3508-3576
7. Dupont, J. On the Solid, Liquid and Solution Structural Organization of Imidazolium Ionic Liquids J. Braz. Chem. Soc 2004, 15, 341-350
8. Antonietti, M.; Kuang, D. B.; Smarsly, B.; Yong, Z. Ionic Liquids for the Convenient Synthesis of Functional Nanoparticles and Other Inorganic Nanostructures. Angew. Chem., Int. Ed. 2004, 43, 4988-4992
9. Dupont, J.; Scholten, J. D. On the Structural and Surface Properties of Transition-Metal Nanoparticles in Ionic Liquids Chem. Soc. Rev. 2010, 39, 1780-1804
10. Neto, B. A. D.; Spencer, J. The Impressive Chemistry, Applications and Features of Ionic Liquids: Properties, Catalysis & Catalysts and Trends J. Braz. Chem. Soc. 2012, 23, 987-1007
11. Gozzo, F. C.; Santos, L. S.; Augusti, R.; Consorti, C. S.; Dupont, J.; Eberlin, M. N. Gaseous Supramolecules of Imidazolium Ionic Liquids: Magic Numbers and Intrinsic Strengths of Hydrogen Bonds Chem. - Eur. J. 2004, 10, 6187-6193
12. Holopainen, S.; Nousiainen, M.; Puton, J.; Sillanpaa, M.; Bardi, U.; Tolstogouzov, A. Evaporation of Ionic Liquids at Atmospheric Pressure: Study by Ion Mobility Spectrometry Talanta 2011, 83, 907-915
13. Hogan, C. J.; de la Mora, J. F. Ion-Pair Evaporation from Ionic Liquid Clusters J. Am. Soc. Mass Spectrom. 2010, 21, 1382-1386
14. Earle, M. J.; Esperanca, J.; Gilea, M. A.; Lopes, J. N. C.; Rebelo, L. P. N.; Magee, J. W.; Seddon, K. R.; Widegren, J. A. Distillation and Volatility of Ionic Liquids Nature 2006, 439, 831-834
15. Taylor, A. W.; Lovelock, K. R. J.; Deyko, A.; Licence, P.; Jones, R. G. High Vacuum Distillation of Ionic Liquids and Separation of Ionic Liquid Mixtures Phys. Chem. Chem. Phys. 2010, 12, 1772-1783
16. Leal, J. P.; da Piedade, M. E. M.; Lopes, J. N. C.; Tomaszowska, A. A.; Esperanca, J.; Rebelo, L. P. N.; Seddon, K. R. Bridging the Gap between Ionic Liquids and Molten Salts: Group 1 Metal Salts of the Bistriflamide Anion in the Gas Phase J. Phys. Chem. B 2009, 113, 3491-3498
17. Wasserscheid, P. Volatile Times for Ionic Liquids Nature 2006, 439, 797-797
18. Rai, N.; Maginn, E. J. Vapor-liquid Coexistence and Critical Behavior of Ionic Liquids via Molecular Simulations J. Phys. Chem. Lett. 2011, 2, 1439-1443
19. Rai, N.; Maginn, E. J. Critical Behaviour and Vapour-Liquid Coexistence of 1-Alkyl-3-Methylimidazolium Bis(Trifluoromethylsulfonyl)Amide Ionic Liquids via Monte Carlo Simulation Faraday Discuss 2012, 154, 53-69
20. Berg, R. W.; Lopes, J. N. C.; Ferreira, R.; Rebelo, L. P. N.; Seddon, K. R.; Tomaszowska, A. A. Raman Spectroscopic Study of the Vapor Phase of L-Methylimidazolium Ethanoate, A Protic Ionic Liquid J. Phys. Chem. A. 2010, 114, 10834-10841
21. Gross, J. H. Molecular Ions of Ionic Liquids in the Gas Phase J. Am. Soc. Mass Spectrom. 2008, 19, 1347-1352
22. Leal, J. P.; Esperanca, J.; da Piedade, M. E. M.; Lopes, J. N. C.; Rebelo, L. P. N.; Seddon, K. R. The Nature of Ionic Liquids in the Gas Phase J. Phys. Chem. A. 2007, 111, 6176-6182
23. Leal, J. P.; da Piedade, M. E. M.; Lopes, J. N. C.; Tomaszowska, A. A.; Esperanca, J.; Rebelo, L. P. N.; Seddon, K. R. Bridging the Gap between Ionic Liquids and Molten Salts: Group 1 Metal Salts of the Bistriflamide Anion in the Gas Phase J. Phys. Chem. B. 2009, 113, 3491-3498
24. Chaban, V. V.; Prezhdo, O. V. Ionic Vapor: What Does It Consist Of? J. Phys. Chem. Lett. 2012, 3, 1657-1662
25. Neto, B. A. D.; Santos, L. S.; Nachtigall, F. M.; Eberlin, M. N.; Dupont, J. On the Species Involved in the Vaporization of Imidazolium Ionic Liquids in a Steam-Distillation-Like Process Angew. Chem., Int. Ed. 2006, 45, 7251-7254
26. Smith, E. F.; Rutten, F. J. M.; Villar-Garcia, I. J.; Briggs, D.; Licence, P. Ionic Liquids in Vacuo: Analysis of Liquid Surfaces Using Ultra-High-Vacuum Techniques Langmuir 2006, 22, 9386-9392
27. Armstrong, J. P.; Hurst, C.; Jones, R. G.; Licence, P.; Lovelock, K. R. J.; Satterley, C. J.; Villar-Garcia, I. J. Vapourisation of Ionic Liquids Phys. Chem. Chem. Phys. 2007, 9, 982-990
28. Chambreau, S. D.; Boatz, J. A.; Vaghjiani, G. L.; Koh, C.; Kostko, O.; Golan, A.; Leone, S. R. Thermal Decomposition Mechanism of 1-Ethyl-3- methylimidazolium Bromide Ionic Liquid J. Phys. Chem. A. 2012, 116, 5867-5876
29. Vitorino, J.; Leal, J. P.; Licence, P.; Lovelock, K. R. J.; Gooden, P. N.; da Piedade, M. E. M.; Shimizu, K.; Rebelo, L. P. N.; Lopes, J. N. C. Vaporisation of a Dicationic Ionic Liquid Revisited ChemPhysChem. 2010, 11, 3673-3677
30. Ballone, P.; Pinilla, C.; Kohanoff, J.; Del Popolo, M. G. Nano-Indentation of a Room-Temperature Ionic Liquid Film on Silica: A Computational Experiment J. Phys. Chem. B. 2007, 111, 4938-4950
31. Kelkar, M. S.; Maginn, E. J. Calculating the Enthalpy of Vaporization for Ionic Liquid Clusters J. Phys. Chem. B. 2007, 111, 9424-9427
32. McLafferty, F. W.; Turecek, F. Interpretation of Mass Spectra, 4 th ed.; University Science Books: Saussalito, CA, 1993.
33. Esperanca, J.; Lopes, J. N. C.; Tariq, M.; Santos, L.; Magee, J. W.; Rebelo, L. P. N. Volatility of Aprotic Ionic Liquids-A Review J. Chem. Eng. Data 2010, 55, 3-12
34. de Hoffmann, E.; Stroobant, V. Mass Spectrometry: Principles and Applications, 3 rd ed.; Wiley: New York, 2007.
35. Chen, H.; Zheng, O. Y.; Cooks, R. G. Thermal Production and Reactions of Organic Ions at Atmospheric Pressure Angew. Chem., Int. Ed. 2006, 45, 3656-3660
36. Dow, A. M.; Wittrig, A. R.; Kenttamaa, H. I. Laser-Induced Acoustic Desorption (LIAD) Mass Spectrometry Eur. J. Mass Spectrom. 2012, 18, 77-92
37. Lovelock, K. R. J.; Deyko, A.; Corfield, J. A.; Gooden, P. N.; Licence, P.; Jones, R. G. Vaporisation of a Dicationic Ionic Liquid ChemPhysChem 2009, 10, 337-340
38. Deyko, A.; Lovelock, K. R. J.; Licence, P.; Jones, R. G. The Vapour Of Imidazolium-Based Ionic Liquids: A Mass Spectrometry Study Phys. Chem. Chem. Phys. 2011, 13, 16841-16850
39. Lovelock, K. R. J.; Deyko, A.; Licence, P.; Jones, R. G. Vaporisation of an Ionic Liquid near Room Temperature Phys. Chem. Chem. Phys. 2010, 12, 8893-8901
40. Deyko, A.; Lovelock, K. R. J.; Corfield, J. A.; Taylor, A. W.; Gooden, P. N.; Villar-Garcia, I. J.; Licence, P.; Jones, R. G.; Krasovskiy, V. G.; Chernikova, E. A.; Kustov, L. M. Measuring and Predicting Delta H-vap(298) Values of Ionic Liquids Phys. Chem. Chem. Phys. 2009, 11, 8544-8555
41. Dupont, J. From Molten Salts to Ionic Liquids: A Nano Journey Acc. Chem. Res. 2011, 44, 1223-1231
42. Becke, A. D. a New Mixing of Hartree-Fock and Local Density-Functional Theories J. Chem. Phys. 1993, 98, 1372-1377
43. Becke, A. D. Density-Functional Thermochemistry. III. The Role of Exact Exchange J. Chem. Phys. 1993, 98, 5648-5652
44. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields J. Phys. Chem. 1994, 98, 11623-11627
45. 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.