[en] The Broensted acidity level was evaluated for several ionic liqs. ([BMIm][BF4], [BMIm][PF6], [BMIm][SbF6], [BMIm][OTf], [BMIm][NTf2], [HNET3][NTf2], and [HBIm][NTf2]) to which a strong acid, such as HNTf2 [NTf2=N(CF3SO2)2] and HOTf (OTf=CF3SO3), has been added. The main purpose is to tentatively measure the influence on the resulting acidity of (i) the solvent anion or cation structure and (ii) the added acid nature. The evaluation method is based on the detn. of the Hammett acidity functions H0 using UV/visible spectroscopy. The acidity of protons is mainly detd. by their solvation state, and consequently, the properties of protons depend on both the nature of the solvent and the nature and concn. of the acid. In practice, for the investigated ionic liqs., the cation as well as the added acid nature does not play a dominant role, whereas changing the anion nature may lead to very different acidities. Indeed, for a similar content of added acid, the measured acidity levels are in the order PF6- > BF4- > NTf2- > OTf-. The problems of the influence of impurities on the final acidity and of the dissocg. character of the ionic liq. are addressed.
Disciplines :
Chemistry
Author, co-author :
Robert, Thierry ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie analytique et électrochimie
Magna, Lionel; Institut Francais du Petrole - IFP
Olivier-Bourbigou, Hélène; Institut Français du Pétrol - IFP
Gilbert, Bernard ; Université de Liège - ULiège > Département de chimie (sciences) > Département de chimie (sciences)
Language :
English
Title :
A Comparison of the Acidity Levels in Room-Temperature Ionic Liquids
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Bibliography
H. Olivier-Bourbigou, in Catalysis in Nonaqueous Ionic Liquids, in Multiphase Homogeneous Catalysis, B. Cornils, W. A. Herrmann, I. T. Horvath, W. Leitner, S. Mecking, H. Olivier-Bourbigou, and, D. Vogt, Editors, Wiley-VCH, Weinheim (2005); Z. Conrad Zhang, Adv. Catal. 0065-2342, 49, 153 (2006) 10.1016/S0360-0564(05)49003-3; V. I. Parvulescu and C. Hardacre, Chem. Rev. (Washington, D.C.) 0009-2665, 107, 2615 (2007) 10.1021/cr050948h; R. Giernoth, Top. Curr. Chem. 0071-7894, 276, 1 (2007) 10.1007/128-016; P. Wasserscheid and T. Welton, in Ionic Liquids in Synthesis, P. Wasserscheid, and, T. Welton, Editors, Wiley-VCH, Weinheim (2008); J. Ross and J. Xiao, Green Chem. 1463-9262, 4, 129 (2002) 10.1039/b109847k; P. Wasserscheid, M. Sesing, and W. Korth, Green Chem. 1463-9262, 4, 134 (2002). 10.1039/b109845b
D. R. MacFarlane, J. M. Pringle, K. M. Johansson, and S. A. Forsyth, Chem. Commun. (Cambridge) 1359-7345, 2006, 1905; K. E. Johnson, R. M. Pagni, and J. Bartmess, Monatsch. Chem. 0026-9247, 138, 1077 (2007) 10.1007/s00706-007- 0755-6; A. A. M. Lapis, B. A. D. Neto, J. Scholten, F. M. Nachtigall, M. N. Eberlin, and J. Dupont, Tetrahedron Lett. 0040-4039, 47, 6775 (2006) 10.1016/j.tetlet.2006.07.073; A. C. Pinto, A. A. M. Lapis, B. V. da Silva, R. S. Bastos, J. Dupont, and B. A. D. Neto, Tetrahedron Lett. 0040-4039, 49, 5639 (2008). 10.1016/j.tetlet.2008.07.067
I. C. Quarmby, R. A. Mantz, L. M. Goldenberg, and R. A. Osteryoung, Anal. Chem. 0003-2700, 66, 3558 (1994) 10.1021/ac00093a004; P. Koronaios, D. King, and R. A. Osteryoung, Inorg. Chem. 0020-1669, 37, 2028 (1998) 10.1021/ic971345u; J. P. Pauly, Ph.D. Thesis, Universit́ de Lìge, Belgium (1997).
D. King, R. Mantz, and R. Osteryoung, J. Am. Chem. Soc. 0002-7863, 118, 11933 (1996) 10.1021/ja961935b; G. P. Smith, A. S. Dworkin, R. M. Pagni, and S. P. Zingg, J. Am. Chem. Soc. 0002-7863, 111, 525 (1989). 10.1021/ja00184a020
A. C. Cole, J. L. Jensen, I. Ntai, K. L. T. Tran, K. J. Weaver, D. C. Forbes, and J. H. Davis, Jr., J. Am. Chem. Soc. 0002-7863, 124, 5962 (2002) 10.1021/ja026290w; Y. Gu, F. Shi, and Y. Deng, Catal. Commun. 1566-7367, 4, 597 (2003). 10.1016/j.catcom.2003.09.004
A. Fernicola, B. Scrosati, and H. Ohno, Ionics 0947-7047, 12, 95 (2006). 10.1007/s11581-006-0023-5
G. Driver and K. Johnson, Green Chem. 1463-9262, 5, 163 (2003). 10.1039/b211548d
T. L. Greaves and C. J. Drummod, Chem. Rev. (Washington, D.C.) 0009-2665, 108, 206 (2008) 10.1021/cr068040u; D. R. MacFarlane and K. R. Seddon, Aust. J. Chem. 0004-9425, 60, 3 (2007) 10.1071/CH06478; K. M. Johanson, E. I. Izgorodina, M. Forsyth, D. R. MacFarlane, and K. R. Seddon, Phys. Chem. Chem. Phys. 1463-9076, 10, 2972 (2008) 10.1039/b801405a; M. Anouti, M. Caillon-Caravanier, C. Le Floch, and D. Lemordant, J. Phys. Chem. B 1089-5647, 112, 9412 (2008) 10.1021/jp803489n; T. L. Greaves, A. Weerawardena, C. Fong, I. Krodkiewska, and C. J. Drummod, J. Phys. Chem. B 1089-5647, 110, 22479 (2006). 10.1021/jp0634048
X. Li, W. Eli, and G. Li, Catal. Commun. 1566-7367, 9, 2264 (2008) 10.1016/j.catcom.2008.05.015; V. Singh, S. Kaur, V. Sapehiyia, J. Singh, and G. L. Kad, Catal. Commun. 1566-7367, 6, 57 (2005) 10.1016/j.catcom.2004.10.011; J. Fraga-Dubreuil, K. Bourahla, M. Rahmouni, J. P. Bazureau, and J. Hamelin, Catal. Commun. 1566-7367, 3, 185 (2002). 10.1016/S1566-7367(02)00087-0
S. Liu, C. Xie, S. Yu, and F. Liu, Catal. Commun. 1566-7367, 9, 2030 (2008). 10.1016/j.catcom.2008.03.045
T. Robert, H. Olivier-Bourbigou, L. Magna, and B. Gilbert, ECS Trans. 1938-5862, 3 (35), 71 (2007). 10.1149/1.2798648
C. Thomazeau, H. Olivier-Bourbigou, L. Magna, S. Luts, and B. Gilbert, J. Am. Chem. Soc. 0002-7863, 125, 5264 (2003). 10.1021/ja0297382
H. Xing, T. Wang, Z. Zhou, and Y. Dai, J. Mol. Catal. A: Chem. 1381-1169, 264, 53 (2007) 10.1016/j.molcata.2006.08.080; M. Anouti, M. Caillon-Caravanier, C. Le Floch, and D. Lemordant, J. Phys. Chem. B 1089-5647, 112, 9406 (2008) 10.1021/jp803483f; M. Anouti, M. Caillon-Caravanier, Y. Dridi, H. Galiano, and D. Lemordant, J. Phys. Chem. B 1089-5647, 112, 13335 (2008). 10.1021/jp805992b
Z. Duan, Y. Gu, J. Zhang, L. Zhu, and Y. Deng, J. Mol. Catal. A: Chem. 1381-1169, 250, 163 (2006) 10.1016/j.molcata.2006.01.035; Q. Bao, K. Qiao, D. Tomida, and C. Yokoyama, Catal. Commun. 1566-7367, 9, 1383 (2008) 10.1016/j.catcom.2007.12.002; X. Liu, J. Zhou, X. Guo, M. Liu, X. Ma, C. Song, and C. Wang, Ind. Eng. Chem. Res. 0888-5885, 47, 5298 (2008) 10.1021/ie070647t; Y. Zhao, J. Long, F. Deng, X. Liu, Z. Li, C. Xia, and J. Peng, Catal. Commun. 1566-7367, 10, 732 (2009) 10.1016/j.catcom.2008.11.030; D. Fang, Q. -R. Shi, J. Cheng, K. Gong, and Z. -L. Liu, Appl. Catal. A: Gen., 345, 158 (2008) 10.1016/j.apcata.2008.04.037; Y. -Y. Wang, W. Li, and L. -Y. Dai, Chin. J. Chem. 1001-604X, 26, 1390 (2008) 10.1002/cjoc.200890253; G. Cheng, X. Duan, X. Qi, and C. Lu, Catal. Commun. 1566-7367, 10, 201 (2008) 10.1016/j.catcom.2008.08. 019; Z. Du, Z. Li, S. Guo, J. Zhang, L. Zhu, and Y. Deng, J. Phys. Chem. B 1089-5647, 109, 19542 (2005). 10.1021/jp0529669
Z. Fei, D. Zhao, T. J. Geldbach, R. Scopelliti, and P. J. Dyson, Chem.-Eur. J. 0947-6539, 10, 4886 (2004). 10.1002/chem.200400145
Y. Chu, H. Deng, and J. Cheng, J. Org. Chem. 0022-3263, 72, 7790 (2007). 10.1021/jo070973i
P. Bonhôte, A. P. Papageorgiou, N. Kalyanasundaram, and M. Grätzel, Inorg. Chem. 0020-1669, 35, 1168 (1996) 10.1021/ic951325x; P. A. Z. Suarez, J. E. L. Dullius, S. Einloft, R. F. de Souza, and J. Dupont, Polyhedron 0277-5387, 15, 1217 (1996) 10.1016/0277-5387(95)00365-7; V. Gallo, P. Mastrorilli, C. F. Nobile, G. Romanazzi, and G. P. Suranna, Dalton Trans. 1477-9226, 23, 4339 (2002).
B. Tŕmillon, Chemistry in Non-Aqueous Solvents, Reidel, Dordrecht (1974); B. Tŕmillon, Electrochimie Analytique et Reactions en Solution, Vol. I, p. 294, Masson, Paris (1993); O. Popovych and R. P. T. Tomkins, Nonaqueous Solution in Chemistry, p. 224, Wiley-Interscience, Berlin (1981).
I. Billard, G. Moutiers, A. Labet, A. El Azzi, C. Gaillard, C. Mariet, and K. Lützenkirchen, Inorg. Chem. 0020-1669, 42, 1726 (2003) 10.1021/ic0260318; A. Paul, P. K. Mandal, and A. Samanta, Chem. Phys. Lett. 0009-2614, 402, 375 (2005). 10.1016/j.cplett.2004.12.060
D'Anna, A. J. Fry, J. Electroanal. Chem., 546, 35 K. J. Fraser, E. I. Izgorodina, M. Forsyth, J. L. Scott, and D. R. MacFarlane, Chem. Commun. (Cambridge), 2007, 3817; F. D’Anna and R. Noto, Tetrahedron, 63, 11681
S. Bruckenstein, J. Am. Chem. Soc. 0002-7863, 82, 307 (1960). 10.1021/ja01487a014
J. P. Hallett, C. L. Liotta, G. Ranieri, and T. Welton, J. Org. Chem. 0022-3263, 74, 1864 (2009). 10.1021/jo802121d
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