Physical properties, ion-ion interactions, and conformational states of ionic liquids with alkyl-phosphonate anions

Journal of Physical Chemistry B

Volumn 117, Issue 27, 2013, Pages 8172-8179

  Pitawala, Jagath ^a   Scheers, Johan ^a   Jacobsson, Per ^a   Matic, Aleksandar ^a  

^a CHALMERS UNIVERSITY OF TECHNOLOGY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

CALCULATIONS; IONIC CONDUCTIVITY; IONIC LIQUIDS; POSITIVE IONS;

ALKYL CHAIN LENGTHS; CATION-ANION INTERACTIONS; CONFORMATIONAL STATE; FIRST-PRINCIPLES CALCULATION; IMIDAZOLIUM CATION; ION-ION INTERACTION; TEMPERATURE BEHAVIOR; VOGEL-FULCHER-TAMMANN EQUATION;

NEGATIVE IONS;

EID: 84880148874     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp4042974     Document Type: Article

References (49)

1. Wilkes, J. S. A Short History of Ionic Liquids-from Molten Salts to Neoteric Solvents Green Chem. 2002, 4, 73-80
2. Ohno, H. Importance and Possibility of Ionic Liquids. In Electrochemical Aspects of Ionic Liquids; Ohno, H., Ed.; John Wiley & Sons, Inc.: Hoboken, NJ, 2005; pp 1-3.
3. Dzyuba, S. V.; Bartsch, R. A. Influence of Structural Variations in 1-Alkyl(aralkyl)-3-methylimidazolium Hexafluorophosphates and Bis(trifluoromethylsulfonyl)imides on Physical Properties of the Ionic Liquids ChemPhysChem. 2002, 3, 161-166
4. Tokuda, H.; Hayamizu, K.; Ishii, K.; Susan, M. A. B. H.; Watanabe, M. Physicochemical Properties and Structures of Room Temperature Ionic Liquids. 2. Variation of Alkyl Chain Length in Imidazolium Cation J. Phys. Chem. B 2005, 109, 6103-6110
5. Tokuda, H.; Ishii, K.; Susan, M. A. B. H.; Tsuzuki, S.; Hayamizu, K.; Watanabe, M. Physicochemical Properties and Structures of Room-Temperature Ionic Liquids. 3. Variation of Cationic Structures J. Phys. Chem. B 2006, 110, 2833-2839
6. Anderson, J. L.; Ding, R.; Ellern, A.; Armstrong, D. W. Structure and Properties of High Stability Geminal Dicationic Ionic Liquids J. Am. Chem. Soc. 2005, 127, 593-604
7. Appetecchi, G. B.; Montanino, M.; Zane, D.; Carewska, M.; Alessandrini, F.; Passerini, S. Effect of the Alkyl Group on the Synthesis and the Electrochemical Properties of N-Alkyl-N-methyl-pyrrolidinium b is(trifluoromethanesulfonyl)imide Ionic Liquids Electrochim. Acta 2009, 54, 1325-1332
8. MacFarlane, D. R.; Pringle, J. M.; Johansson, K. M.; Forsyth, S. A.; Forsyth, M. Lewis Base Ionic Liquids Chem. Commun. 2006, 1905-1917
9. Ueno, K.; Tokuda, H.; Watanabe, M. Ionicity in Ionic Liquids: Correlation with Ionic Structure and Physicochemical Properties Phys. Chem. Chem. Phys. 2010, 12, 1649-1658
10. Zhou, Z.-B.; Matsumoto, H.; Tatsumi, K. Structure and Properties of New Ionic Liquids Based on Alkyl- and Alkenyltrifluoroborates ChemPhysChem. 2005, 6, 1324-1332
11. 19F NMR Ionic Diffusion Coefficient, Viscosity, and Ionic Conductivity of Non-Chloroaluminate Room-Temperature Ionic Liquids J. Phys. Chem. B 2001, 105, 4603-4610
12. Matsumoto, H.; Kageyama, H.; Miyazaki, Y. Room Temperature Ionic Liquids Based on Small Aliphatic Ammonium Cations and Asymmetric Amide Anions Chem. Commun. 2002, 1726-1727
13. Tokuda, H.; Hayamizu, K.; Ishii, K.; Susan, M. A. B. H.; Watanabe, M. Physicochemical Properties and Structures of Room Temperature Ionic Liquids. 1. Variation of Anionic Species J. Phys. Chem. B 2004, 108, 16593-16600
14. Kunze, M.; Jeong, S.; Paillard, E.; Winter, M.; Passerini, S. Melting Behavior of Pyrrolidinium-Based Ionic Liquids and Their Binary Mixtures J. Phys. Chem. C 2010, 114, 12364-12369
15. Seki, S.; Kobayashi, T.; Kobayashi, Y.; Takei, K.; Miyashiro, H.; Hayamizu, K.; Tsuzuki, S.; Mitsugi, T.; Umebayashi, Y. Effects of Cation and Anion on Physical Properties of Room-Temperature Ionic Liquids J. Mol. Liq. 2010, 152, 9-13
16. Tokuda, H.; Tsuzuki, S.; Susan, M. A. B. H.; Hayamizu, K.; Watanabe, M. How Ionic Are Room-Temperature Ionic Liquids? An Indicator of the Physicochemical Properties J. Phys. Chem. B 2006, 110, 19593-19600
17. Wasserscheid, P.; Hal, R. V.; Bösmann, A. 1- n -Butyl-3- methylimidazolium ([bmim]) Octylsulfate-An Even 'Greener' Ionic Liquid Green Chem. 2002, 4, 400-404
18. Shah, F. U.; Glavatskih, S.; MacFarlane, D. R.; Somers, A.; Forsyth, M.; Antzutkin, O. N. Novel Halogen-Free Chelated Orthoborate-Phosphonium Ionic Liquids: Synthesis and Tribophysical Properties Phys. Chem. Chem. Phys. 2011, 13, 12865-12873
19. Bonhoîte, P.; Dias, A.-P.; Papageorgiou, N.; Kalyanasundaram, K.; Grätzel, M. Hydrophobic, Highly Conductive Ambient-Temperature Molten Salts Inorg. Chem. 1996, 35, 1168-1178
20. Henderson, W. A.; Passerini, S. Phase Behavior of Ionic Liquid-LiX Mixtures: Pyrrolidinium Cations and TFSI-Anions Chem. Mater. 2004, 16, 2881-2885
21. Martinelli, A.; Matic, A.; Jacobsson, P.; Börjesson, L. Phase Behavior and Ionic Conductivity in Lithium Bis(trifluoromethanesulfonyl)imide- Doped Ionic Liquids of the Pyrrolidinium Cation and Bis(trifluoromethanesulfonyl)imide Anion J. Phys. Chem. B 2009, 113, 11247-11251
22. Zhou, Q.; Fitzgerald, K.; Boyle, P. D.; Henderson, W. A. Phase Behavior and Crystalline Phases of Ionic Liquid-Lithium Salt Mixtures with 1-Alkyl-3-methylimidazolium Salts Chem. Mater. 2010, 22, 1203-1208
23. Kuhlmann, E.; Himmler, S.; Giebelhaus, H.; Wasserscheid, P. Imidazolium Dialkylphosphates-A Class of Versatile, Halogen-Free and Hydrolytically Stable Ionic Liquids Green Chem. 2007, 9, 233-242
24. Nishi, N.; Kawakami, T.; Shigematsu, F.; Yamamoto, M.; Kakiuchi, T. Fluorine-Free and Hydrophobic Room-Temperature Ionic Liquids, Tetraalkylammonium Bis(2-ethylhexyl)sulfosuccinates, and Their Ionic Liquid-Water Two-Phase Properties Green Chem. 2006, 8, 349-355
25. 2] in Dependence on Temperature at Atmospheric Pressure J. Chem. Eng. Data 2009, 54, 2576-2583
26. - Anions with Potential Application for Corrosion Mitigation of Magnesium Alloys Electrochim. Acta 2008, 54, 254-260
27. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A., Gaussian 09, revision A.1; Gaussian, Inc.: Wallingford, CT, 2009.
28. Ohno, H. Functional Design of Ionic Liquids Bull. Chem. Soc. Jpn. 2006, 79, 1665-1680
29. Holbrey, J. D.; Seddon, K. R. The Phase Behaviour of 1-Alkyl-3- methylimidazolium Tetrafluoroborates; Ionic Liquids and Ionic Liquid Crystals J. Chem. Soc., Dalton Trans. 1999, 2133-2139
30. Schreiner, C.; Zugmann, S.; Hartl, R.; Gores, H. J. J. Fractional Walden Rule for Ionic Liquids: Examples from Recent Measurements and a Critique of the So-Called Ideal KCl Line for the Walden Plot Chem. Eng. Data 2010, 55, 1784-1788
31. Appetecchi, G. B.; Montanino, M.; Carewska, M.; Moreno, M.; Alessandrini, F.; Passerini, S. Chemical-Physical Properties of Bis(perfluoroalkylsulfonyl) imide-Based Ionic Liquids Electrochim. Acta 2011, 56, 1300-1307
32. Leys, J.; Wübbenhorst, M.; Menon, C. P.; Rajesh, R.; Thoen, J.; Glorieux, C.; Nockemann, P.; Thijs, B.; Binnemans, K.; Longuemart, S. Temperature Dependence of the Electrical Conductivity of Imidazolium Ionic Liquids J. Chem. Phys. 2008, 128, 064509-1-064509-7
33. Tamman, G.; Hesse, W. Z. The Dependency of Viscosity on Temperature in Hypothermic Liquids Z. Anorg. Allg. Chem. 1926, 156, 245-257
34. Martinelli, A.; Matic, A.; Jacobsson, P.; Börjesson, L.; Fernicola, A.; Panero, S.; Scorsati, B.; Ohno, H. Physical Properties of Proton Conducting Membranes Based on a Protic Ionic Liquid J. Phys. Chem. B 2007, 111, 12462-12467
35. Bandrés, I.; Montaño, D. F.; Gascón, I.; Cea, P.; Lafuente, C. Study of the Conductivity Behavior of Pyridinium-Based Ionic Liquids Electrochim. Acta 2010, 55, 2252-2257
36. Lassègues, J. C.; Grondin, J.; Holomb, R.; Johansson, P. Raman and Ab Initio Study of the Conformational Isomerism in the 1-Ethyl-3-methyl- imidazolium Bis(trifluoromethanesulfonyl)imide Ionic Liquid J. Raman Spectrosc. 2007, 38, 551-558
37. Ribeiro, M. C. High Viscosity of Imidazolium Ionic Liquids with the Hydrogen Sulfate Anion: A Raman Spectroscopy Study J. Phys. Chem. B 2012, 116, 7281-7290
38. Jeon, Y.; Sung, J.; Seo, C.; Lim, H.; Cheong, H.; Kang, M.; Moon, B.; Ouchi, Y.; Kim, D. Structures of Ionic Liquids with Different Anions Studied by Infrared Vibration Spectroscopy J. Phys. Chem. B 2008, 112, 4735-4740
39. Grondin, J.; Lassègues, J. C.; Cavagnat, D.; Buffeteau, T.; Johansson, P.; Holomb, R. Revisited Vibrational Assignments of Imidazolium-Based Ionic Liquids J. Raman Spectrosc. 2011, 42, 733-743
40. Angenendt, K.; Johansson, P. Ionic Liquid Based Lithium Battery Electrolytes: Charge Carriers and Interactions Derived by Density Functional Theory Calculations J. Phys. Chem. B 2011, 115, 7808-7813
41. Doak, G. O.; Freedman, L. D. The Structure and Properties of the Dialkyl Phosphonates Chem. Rev. 1961, 61, 31-44
42. Georgiev, E. M.; Kaneti, J.; Troev, K.; Roundhill, D. M. An Ab-Initio Study of the Mechanism of the Atherton-Todd Reaction Between Dimethyl Phosphonate and Chlorosubstituted and Fluoro-Substituted Methanes J. Am. Chem. Soc. 1993, 115, 10964-10973
43. 2P(O)H J. Mol. Struct. 1992, 269, 1-21
44. Moravie, R. M.; Froment, F.; Corset, J. Vibrational-Spectra and Possible Conformers of Dimethylphosphonate by Normal Mode Analysis Spectrochim. Acta 1989, 45, 1015-1024
45. Strajbl, M.; Baumruk, V.; Florián, J.; Bednárová, L.; Rosenberg, I.; Stepánek, J. Molecular Structure, Vibrational Spectra and Quantum Mechanical Force Fields of Modified Oligonucleotide Linkages: 1. Methyl Methoxymethanphosphonate J. Mol. Struct. 1997, 415, 161-177
46. Carauta, A. N. M.; de Souza, V.; Hollauer, E.; Téllez, S. Vibrational Study of Dialkylphosphonates: Di-n-Propyl- and Di-i- Propylphosphonates by Semiempirical and Ab Initio Methods Spectrochim. Acta, Part A 2004, 60, 41-51
47. Carauta, A. N. M.; de M. Carneiro, J. W.; Soto, C. A. T. Conformational and Vibrational Study of Di-n-Propyl and Di-i-Propylphosphonates by MM/QM Method Int. J. Quantum Chem. 2005, 103, 763-774
48. Umebayashi, Y.; Fujimori, T.; Sukizaki, T.; Asada, M.; Fujii, K.; Kanzaki, R.; Ishiguro, S.-I. Evidence of Conformational Equilibrium of 1-Ethyl-3-methylimidazolium in Its Ionic Liquid Salts: Raman Spectroscopic Study and Quantum Chemical Calculations J. Phys. Chem. A 2005, 109, 8976-8982
49. Meyrick, C. I.; Thompson, H. W. Vibrational Spectra of Alkyl Esters of Phosphorus Oxy-Acids J. Chem. Soc. 1950, 225-229