Abstract
Although many ionic liquids have been reported, their polarity is not completely understood. Different empirical polarity scales for molecular solvents always lead to different polarity orders when they are applied on ionic liquids. Based on a literature survey, this review summarizes the recent polarity scales of ionic liquids according to the following 4 classes: (1) equilibrium and kinetic rate constants of chemical reactions; (2) empirical polar parameters of ionic liquids; (3) spectral properties of probe molecules; (4) multiparameter approaches. In addition, their interrelations are presented. A systematic understanding of the relationship between different polarity parameters of ionic liquids is of great importance for finding a universal set of parameters that can be used to predict the polarities of ionic liquids quantitatively. The potential utilization of the electron paramagnetic resonance in this field is also addressed.
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References
Reichardt C. Solvents and Solvent Effects in Organic Chemistry. Weinheim: Wiley-VCH, 2003
Katritzky AR, Fara DC, Yang HF, Tamm K, Tamm T, Karelson M. Chem Rev, 2004, 104: 175–198
Chiappe C, Pieraccini D. J Phys Org Chem, 2005, 18: 275–297
Hallett JP, Welton T. Chem Rev, 2011, 111: 3508–3576
Shukla SK, Kumar A. Clean Technol Envir, 2015, 17: 1111–1116
Weingaertner H. Angew Chem Int Ed, 2008, 47: 654–670
Xu YJ, Zhu X, Li HR. Sci Sinica Chim, 2014, 44: 877–888
Angelini G, Chiappe C, De Maria P, Fontana A, Gasparrini F, Pieraccini D, Pierini M, Siani G. J Org Chem, 2005, 70: 8193–8196
Zappacosta R, Di Crescenzo A, Di Profio P, Fontana A, Siani G. J Org Chem, 2015, 80: 2333–2338
Kirkwood JG. J Chem Phys, 1934, 2: 351–361
Onsager L. J Am Chem Soc, 1936, 58: 1486–1493
Kamlet MJ, Taft RW. J Am Chem Soc, 1976, 98: 377–383
Taft RW, Kamlet MJ. J Am Chem Soc, 1976, 98: 2886–2894
Yokoyama T, Taft RW, Kamlet MJ. J Am Chem Soc, 1976, 98: 3233–3237
Kamlet MJ, Abboud JL, Taft RW. J Am Chem Soc, 1977, 99: 6027–6038
Byrne R, Coleman S, Gallagher S, Diamond D. Phys Chem Chem Phys, 2010, 12: 1895–1904
Creary X, Willis ED, Gagnon M. J Am Chem Soc, 2005, 127: 18114–18120
Lancaster NL, Welton T, Young GB. J Chem Soc Perk T 2, 2001, 12: 2267–2270
Lancaster NL, Salter PA, Welton T, Young GB. J Org Chem, 2002, 67: 8855–8861
Lancaster NL, Welton T. J Org Chem, 2004, 69: 5986–5992
Crowhurst L, Falcone R, Lancaster NL, Llopis-Mestre V, Welton T. J Org Chem, 2006, 71: 8847–8853
Weingartner H, Knocks A, Schrader W, Kaatze U. J Phys Chem A, 2001, 105: 8646–8650
Weingartner H. J Mol Liq, 2014, 192: 185–190
Wakai C, Oleinikova A, Ott M, Weingartner H. J Phys Chem B, 2005, 109: 17028–17030
Daguenet C, Dyson PJ, Krossing I, Oleinikova A, Slattery J, Wakai C, Weingartner H. J Phys Chem B, 2006, 110: 12682–12688
Weingartner H. Z Phys Chem, 2006, 220: 1395–1405
Huang MM, Weingartner H. ChemPhysChem, 2008, 9: 2172–2173
Huang MM, Jiang YP, Sasisanker P, Driver GW, Weingartner H. J Chem Eng Data, 2011, 56: 1494–1499
Bulut S, Klose P, Huang MM, Weingartner H, Dyson PJ, Laurenczy G, Friedrich C, Menz J, Kummerer K, Krossing I. Chem-Eur J, 2010, 16: 13139–13154
Ekimova M, Frohlich D, Stalke S, Lenzer T, Oum K. Chem- PhysChem, 2012, 13: 1854–1859
Jin H, Baker GA, Arzhantsev S, Dong J, Maroncelli M. J Phys Chem B, 2007, 111: 7291–7302
Luo HM, Baker GA, Dai S. J Phys Chem B, 2008, 112: 10077–10081
Jin H, O’Hare B, Dong J, Arzhantsev S, Baker GA, Wishart JF, Benesi AJ, Maroncelli M. J Phys Chem B, 2008, 112: 81–92
Deng LS, Wang Q, Chen YL, Zhang ZF, Tang J. J Mol Liq, 2013, 187: 246–251
Chen YL, Wang Q, Zhang ZF, Tang J. Ind Eng Chem Res, 2012, 51: 15293–15298
Zhang ZH, Wei J, Ma XX, Xu WG, Tong J, Guan W, Yang JZ. Sci Sinica Chim, 2014, 44: 1005–1013
Wei J, Bu XX, Guan W, Xing NN, Fang DW, Wu Y. Rsc Adv, 2015, 5: 70333–70338
Zaitsau DH, Yermalayeu VA, Emel’yanenko VN, Verevkin SP, Welz-biermann U, Schubert T. Sci China Chem, 2012, 55: 1525–1531
Wei J, Ma TY, Ma XX, Guan W, Liu QS, Yang JZ. Rsc Adv, 2014, 4: 30725–30732
Hong M, Liu RJ, Yang HX, Guan W, Tong J, Yang JZ. J Chem Thermodyn, 2014, 70: 214–218
Jarvas G, Quellet C, Dallos A. Fluid Phase Equilibr, 2011, 309: 8–14
Reichardt C. ACS Sym Ser, 2005, 7: 339–351
Reichardt C. Angew Chem Int Ed, 1965, 4: 29–40
Carmichael AJ, Seddon KR. J Phys Org Chem, 2000, 13: 591–595
Zhang SG, Qi XJ, Ma XY, Lu LJ, Deng YQ. J Phys Chem B, 2010, 114: 3912–3920
Muldoon MJ, Gordon CM, Dunkin IR. J Chem Soc Perk T 2, 2001, 4: 433–435
Akdogan Y, Heller J, Zimmermann H, Hinderberger D. Phys Chem Chem Phys, 2010, 12: 7874–7882
Mladenova BY, Kattnig DR, Grampp G. J Phys Chem B, 2011, 115: 8183–8198
Kawai A, Hidemori T, Shibuya K. Chem Lett, 2004, 33: 1464–1465
Strehmel V, Lungwitz R, Rexhausen H, Spange S. New J Chem, 2010, 34: 2125–2131
Strehmel V, Laschewsky A, Stoesser R, Zehl A, Herrmann W. J Phys Org Chem, 2006, 19: 318–325
Strehmel V. Macromol Symp, 2007, 254: 25–33
Nunes P, Nagy NV, Alegria E, Pombeiro AJL, Correia I. Inorg Chim Acta, 2014, 409: 465–471
Nunes P, Nagy NV, Alegria E, Pombeiro AJL, Correia I. J Mol Struct, 2014, 1060: 142–149
Strehmel V, Berdzinski S, Rexhausen H. J Mol Liq, 2014, 192: 153–170
Fujisawa T, Fukuda M, Terazima M, Kimura Y. J Phys Chem A, 2006, 110: 6164–6172
Kimura Y, Fukuda M, Fujisawa T, Terazima M. Chem Lett, 2005, 34: 338–339
Cha DK, Kloss AA, Tikanen AC, Fawcett WR. Phys Chem Chem Phys, 1999, 1: 4785–4790
Fletcher KA, Storey IA, Hendricks AE, Pandey S, Pandey S. ACS Sym Ser, 2001, 3: 210–215
Karmakar R, Samanta A. J Phys Chem A, 2002, 106: 6670–6675
Karmakar R, Samanta A. J Phys Chem A, 2003, 107: 7340–7346
Mandal PK, Samanta A. J Phys Chem B, 2005, 109: 15172–15177
Kashyap HK, Biswas R. J Phys Chem B, 2010, 114: 16811–16823
Zech O, Hunger J, Sangoro JR, Iacob C, Kremer F, Kunz W, Buchner R. Phys Chem Chem Phys, 2010, 12: 14341–14350
Contreras R, Aizman A, Tapia RA, Cerda-Monje A. J Phys Chem B, 2013, 117: 1911–1920
Klein R, Zech O, Maurer E, Kellermeier M, Kunz W. J Phys Chem B, 2011, 115: 8961–8969
Kurnia KA, Lima F, Claudio AFM, Coutinho JAP, Freire MG. Phys Chem Chem Phys, 2015, 17: 18980–18990
Crowhurst L, Mawdsley PR, Perez-Arlandis JM, Salter PA, Welton T. Phys Chem Chem Phys, 2003, 5: 2790–2794
Wu YS, Sasaki T, Kazushi K, Seo T, Sakurai K. J Phys Chem B, 2008, 112: 7530–7536
Acree WE, Abraham MH. J Chem Technol Biot, 2006, 81: 1441–1446
Abraham MH. Chem Soc Rev, 1993, 22: 73–83
Poole SK, Poole CF. Analyst, 1995, 120: 289–294
Poole CF. J Chromatogr A, 2004, 1037: 1–1
Lee SB. J Chem Technol Biot, 2005, 80: 133–137
Del Valle JC, Blanco FG, Catalan J. J Phys Chem B, 2015, 119: 4683–4692
Pandey A, Rai R, Pal M, Pandey S. Phys Chem Chem Phys, 2014, 16: 1559–1568
Kawai A, Hidemori T, Shibuya K. Chem Phys Lett, 2005, 414: 378–383
Miyake Y, Akai N, Kawai A, Shibuya K. J Phys Chem A, 2011, 11: 6347–6356
Baker GA, Rachford AA, Castellano FN, Baker SN. ChemPhysChem, 2013, 14: 1025–1030
Aparicio S, Atilhan M, Khraisheh M, Alcalde R. J Phys Chem B, 2011, 115: 12473–12486
Singh T, Rao KS, Kumar A. ChemPhysChem, 2011, 12: 836–845
Simijonovic D, Petrovic ZD, Petrovic VP. J Mol Liq, 2013, 179: 98–103
Ladesov AV, Kosyakov DS, Bogolitsyn KG, Gorbova NS. Russ J Phys Chem A, 2015, 89: 1814–1820
Zhang PF, Gong YT, Lv YQ, Guo Y, Wang Y, Wang CM, Li HR. Chem Commun, 2012, 48: 2334–2336
Funasako Y, Mochida T, Takahashi K, Sakurai T, Ohta H. Chem-Eur J, 2012, 18: 11929–11936
Ding F, Zheng JJ, Chen YQ, Chen KH, Cui GK, Li HR, Wang CM. Ind Eng Chem Res, 2014, 53: 18568–18574
Shen MM, Che SY, Zhang YY, Yao J, Li HR. J Chem Eng Data, 2014, 59: 3960–3968
Ueda T, Mochida T. Organometallics, 2015, 34: 1279–1286
Komurasaki A, Funasako Y, Mochida T. Dalton T, 2015, 44: 7595–7605
Funasako Y, Kaneshige K, Inokuchi M, Hosokawa H, Mochida T. J Organomet Chem, 2015, 797: 120–124
Lynden-bell RM, Del Popolo MG, Youngs TGA, Kohanoff J, Hanke CG, Harper JB, Pinilla CC. Acc Chem Res, 2007, 40: 1138–1145
Fumino K, Ludwig R. J Mol Liq, 2014, 192: 94–102
Derecskei B, Derecskei-Kovacs A. Mol Sim, 2008, 34: 1167–1175
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Wang, X., Chen, K., Yao, J. et al. Recent progress in studies on polarity of ionic liquids. Sci. China Chem. 59, 517–525 (2016). https://doi.org/10.1007/s11426-016-5579-y
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DOI: https://doi.org/10.1007/s11426-016-5579-y