Artículos de revistas
Solid, Solution And Gas Phase Interactions Of An Imidazolium-based Task-specific Ionic Liquid Derived From Natural Kojic Acid
Registro en:
Journal Of The Brazilian Chemical Society. Sociedade Brasileira De Quimica, v. 25, n. 12, p. 2280 - 2294, 2014.
1035053
10.5935/0103-5053.20140220
2-s2.0-84919344061
Autor
Neto B.A.D.
Mota A.A.R.
Gatto C.C.
Machado G.
Fasciotti M.
De Oliveira H.C.B.
Ferreira D.A.C.
Bianchi O.
Eberlin M.N.
Institución
Resumen
An imidazolium-based task-specific ionic liquid derived from the natural kojic acid had its supramolecular interactions investigated in solid, solution and gas phase. The use of a set of techniques formed by single-crystal X-ray diffraction, nuclear magnetic resonance (NMR) spectroscopy, UV-Vis spectrophotometry, conductivity measurements, small angle X-ray scattering (SAXS), electrospray (tandem) mass spectrometry (ESI-MS(/MS)), and theoretical calculations allowed a deep investigation of the structural organization of the task-specific ionic liquid and its supramolecular interactions. 25 12 2280 2294 Fei, Z., Dyson, P.J., (2013) Chem. Commun., 49, p. 2594 Dupont, J., (2011) Acc. Chem. Res., 44, p. 1223 Dupont, J., Scholten, J.D., (2010) Chem. Soc. Rev., 39, p. 1780 Plechkova, N.V., Seddon, K.R., (2008) Chem. Soc. Rev., 37, p. 123 Hallett, J.P., Welton, T., (2011) Chem. Rev., 111, p. 3508 Scholten, J.D., Leal, B.C., Dupont, J., (2012) ACS Catal., 2, p. 184 Dupont, J., Meneghetti, M.R., (2013) Curr. Opin. Colloid Interface Sci., 18, p. 54 Dupont, J., Eberlin, M.N., (2013) Curr. Org. Chem., 17, p. 257 Petkovic, M., Seddon, K.R., Rebelo, L.P.N., Pereira, C.S., (2011) Chem. Soc. Rev., 40, p. 1383 Suarez, P.A.Z., Ramalho, H.F., (2013) Curr. Org. Chem., 17, p. 229 Olivier-Bourbigou, H., Magna, L., Morvan, D., (2010) Appl. Catal., A, 373, p. 1 Dong, K., Zhang, S.J., (2012) Chem. Eur. J., 18, p. 2748 Van Rantwijk, F., Sheldon, R.A., (2007) Chem. Rev., 107, p. 2757 Parvulescu, V.I., Hardacre, C., (2007) Chem. Rev., 107, p. 2615 Tang, S.K., Baker, G.A., Zhao, H., (2012) Chem. Soc. Rev., 41, p. 4030 Freire, M.G., Claudio, A.F.M., Araujo, J.M.M., Coutinho, J.A.P., Marrucho, I.M., Lopes, J.N.C., Rebelo, L.P.N., (2012) Chem. Soc. Rev., 41, p. 4966 Niedermeyer, H., Hallett, J.P., Villar-Garcia, I.J., Hunt, P.A., Welton, T., (2012) Chem. Soc. Rev., 41, p. 7780 Riduan, S.N., Zhang, Y.G., (2013) Chem. Soc. Rev., 42, p. 9055 Bica, K., Gaertner, P., (2008) Eur. J. Org. Chem., p. 3235 Prechtl, M.H.G., Scholten, J.D., Neto, B.A.D., Dupont, J., (2009) Curr. Org. Chem., 13, p. 1259 Sharma, R., Mahajan, R.K., (2014) RSC Adv., 4, p. 748 Weingartner, H., Cabrele, C., Herrmann, C., (2012) Phys. Chem. Chem. Phys., 14, p. 415 Ueno, K., Tokuda, H., Watanabe, M., (2010) Phys. Chem. Chem. Phys., 12, p. 1649 Fumino, K., Reichert, E., Wittler, K., Hempelmann, R., Ludwig, R., (2012) Angew. Chem., Int. Ed., 51, p. 6236 Tsuzuki, S., Tokuda, H., Mikami, M., (2007) Phys. Chem. Chem. Phys., 9, p. 4780 Peppel, T., Roth, C., Fumino, K., Paschek, D., Kockerling, M., Ludwig, R., (2011) Angew. Chem., Int. Ed., 50, p. 6661 Lassegues, J.C., Grondin, J., Cavagnat, D., Johansson, P., (2009) J. Phys. Chem. A, 113, p. 6419 Danten, Y., Cabaco, M.I., Besnard, M., (2009) J. Phys. Chem. A, 113, p. 2873 Zhao, W., Leroy, F., Heggen, B., Zahn, S., Kirchner, B., Balasubramanian, S., Muller-Plathe, F., (2009) J. Am. Chem. Soc., 131, p. 15825 Wang, X.Q., Yu, L., Jiao, J.J., Zhang, H.N., Wang, R., Chen, H., (2012) J. Mol. Liq., 173, p. 103 Schrekker, H.S., Silva, D.O., Gelesky, M.A., Stracke, M.P., Schrekker, C.M.L., Gonc¸alves, R.S., Dupont, J., (2008) J. Braz.Chem. Soc., 19, p. 426 Cho, C.W., Jungnickel, C., Stolte, S., Preiss, U., Arning, J., Ranke, J., Krossing, I., Thoming, J., (2012) ChemPhysChem, 13, p. 780 Twu, P., Zhao, Q.C., Pitner, W.R., Acree, W.E., Baker, G.A., Anderson, J.L., (2011) J. Chromatogr. A, 1218, p. 5311 Luo, S.C., Sun, S.W., Deorukhkar, A.R., Lu, J.T., Bhattacharyya, A., Lin, I.J.B., (2011) J. Mater. Chem., 21, p. 1866 Liu, X.M., Song, Z.X., Wang, H.J., (2009) Struct. Chem., 20, p. 509 Gutowski, K.E., Maginn, E.J., (2008) J. Am. Chem. Soc., 130, p. 14690 Yu, G.R., Zhang, S.J., Zhou, G.H., Liu, X.M., Chen, X.C., (2007) AIChE J., 53, p. 3210 Paul, A., Samanta, A., (2007) J. Phys. Chem. B, 111, p. 4724 Zhang, Q.H., Li, Z.P., Zhang, J., Zhang, S.G., Zhu, L.Y., Yang, J., Zhang, X.P., Deng, Y.Q., (2007) J. Phys. Chem. B, 111, p. 2864 Saha, S., Hamaguchi, H.O., (2006) J. Phys. Chem. B, 110, p. 2777 Fei, Z.F., Zhao, D.B., Geldbach, T.J., Scopelliti, R., Dyson, P.J., (2005) Eur. J. Inorg. Chem., 860 Lee, K.M., Chang, H.C., Jiang, J.C., Lu, L.C., Hsiao, C.J., Lee, Y.T., Lin, S.H., Lin, I.J.B., (2004) J. Chem. Phys., 120, p. 8645 Stancik, C.M., Lavoie, A.R., Schutz, J., Achurra, P.A., Lindner, P., Gast, A.P., Waymouth, R.M., (2004) Langmuir, 20, p. 596 Allen, J.J., Schneider, Y., Kail, B.W., Luebke, D.R., Nulwala, H., Damodaran, K., (2013) J. Phys. Chem. B, 117, p. 3877 Katsyuba, S.A., Vener, M.V., Zvereva, E.E., Fei, Z.F., Scopelliti, R., Laurenczy, G., Yan, N., Dyson, P.J., (2013) J. Phys. Chem. B, 117, p. 9094 Lee, S.G., (2006) Chem. Commun., p. 1049 Lombardo, M., Trombini, C., (2010) ChemCatChem, 2, p. 135 Sebesta, R., Kmentova, I., Toma, S., (2008) Green Chem., 10, p. 484 Zhang, H., Cui, H., (2009) Langmuir, 25, p. 2604 Lissner, E., De Souza, W.F., Ferrera, B., Dupont, J., (2009) ChemSusChem, 2, p. 962 Li, J.Z., Peng, Y.Q., Song, G.H., (2005) Catal. Lett., 102, p. 159 Dong, F., Jun, L., Xinli, Z., Zhiwen, Y., Zuliang, L., (2007) J. Mol. Catal. A: Chem., 274, p. 208 Safari, J., Zarnegar, Z., (2014) New J. Chem., 38, p. 358 Sharma, N., Sharma, U.K., Kumar, R., Richa, Sinha, A.K., (2012) RSC Adv., 2, p. 10648 Wang, L., Li, H.J., Li, P.H., (2009) Tetrahedron, 65, p. 364 Siyutkin, D.E., Kucherenko, A.S., Struchkova, M.I., Zlotin, S.G., (2008) Tetrahedron Lett., 49, p. 1212 Anjaiah, S., Chandrasekhar, S., Gree, R., (2004) Tetrahedron Lett., 45, p. 569 Geldbach, T.J., Dyson, P.J., (2004) J. Am. Chem. Soc., 126, p. 8114 Zhu, A.L., Jiang, T., Han, B.X., Huang, J., Zhang, J.C., Ma, X.M., (2006) New J. Chem., 30, p. 736 Ramos, L.M., Guido, B.C., Nobrega, C.C., Corrêa, J.R., Silva, R.G., De Oliveira, H.C.B., Gomes, A.F., Neto, B.A.D., (2013) Chem. Eur. J., 19, p. 4156 Alvim, H.G.O., De Lima, T.B., De Oliveira, H.C.B., Gozzo, F.C., De Macedo, J.L., Abdelnur, P.V., Silva, W.A., Neto, B.A.D., (2013) ACS Catal., 3, p. 1420 Alvim, H.G.O., Bataglion, G.A., Ramos, L.M., De Oliveira, A.L., De Oliveira, H.C.B., Eberlin, M.N., De Macedo, J.L., Neto, B.A.D., (2014) Tetrahedron, 70, p. 3306 Oliveira, F.F.D., Dos Santos, M.R., Lalli, P.M., Schmidt, E.M., Bakuzis, P., Lapis, A.A.M., Monteiro, A.L., Neto, B.A.D., (2011) J. Org. Chem., 76, p. 10140 Medeiros, G.A., Da Silva, W.A., Bataglion, G.A., Ferreira, D.A.C., De Oliveira, H.C.B., Eberlin, M.N., Neto, B.A.D., (2014) Chem. Commun., 50, p. 338 Rodrigues, T.S., Silva, V.H.C., Lalli, P.M., De Oliveira, H.C.B., Da Silva, W.A., Coelho, F., Eberlin, M.N., Neto, B.A.D., (2014) J. Org. Chem., 79, p. 5239 Alvim, H.G.O., Lima, T.B., De Oliveira, A.L., De Oliveira, H.C.B., Silva, F.M., Gozzo, F.C., Souza, R.Y., Neto, B.A.D., (2014) J. Org. Chem., 79, p. 3383 Diniz, J.R., Correa, J.R., Moreira, D.D., Fontenele, R.S., De Oliveira, A.L., Abdelnur, P.V., Dutra, J.D.L., Neto, B.A.D., (2013) Inorg. Chem., 52, p. 10199 Dos Santos, M.R., Diniz, J.R., Arouca, A.M., Gomes, A.F., Gozzo, F.C., Tamborim, S.M., Parize, A.L., Neto, B.A.D., (2012) ChemSusChem, 5, p. 716 Dos Santos, M.R., Gomes, A.F., Gozzo, F.C., Suarez, P.A.Z., Neto, B.A.D., (2012) ChemSusChem, 5, p. 2383 Dos Santos, M.R., Coriolano, R., Godoi, M.N., Monteiro, A.L., De Oliveira, H.C.B., Eberlin, M.N., Neto, B.A.D., (2014) New J. Chem., 38, p. 2958 Mota, A.A.R., Gatto, C.C., Machado, G., De Oliveira, H.C.B., Fasciotti, M., Bianchi, O., Eberlin, M.N., Neto, B.A.D., (2014) J. Phys. Chem. C, 118, p. 17878 Dupont, J., Suarez, P.A.Z., De Souza, R.F., Burrow, R.A., Kintzinger, J.P., (2000) Chem. Eur. J., 6, p. 2377 Consorti, C.S., Suarez, P.A.Z., De Souza, R.F., Burrow, R.A., Farrar, D.H., Lough, A.J., Loh, W., Dupont, J., (2005) J. Phys. Chem. B, 109, p. 4341 Steiner, T., (2002) Angew. Chem., Int. Ed., 41, p. 48 Corvo, M.C., Sardinha, J., Menezes, S.C., Einloft, S., Seferin, M., Dupont, J., Casimiro, T., Cabrita, E.J., (2013) Angew. Chem., Int. Ed., 52, p. 13024 Otrelo-Cardoso, A.R., Schwuchow, V., Rodrigues, D., Cabrita, E.J., Leimkuehler, S., Romao, M.J., Santos-Silva, T., (2014) PLoS One, 9, p. e87295 Figueiredo, A.M., Sardinha, J., Moore, G.R., Cabrita, E.J., (2013) Phys. Chem. Chem. Phys., 15, p. 19632 Casimiro, M.H., Corvo, M.C., Ramos, A.M., Cabrita, E.J., Ramos, A.M., Ferreira, L.M., (2013) Mater. Chem. Phys., 138, p. 11 Vold, R.L., Waught, J.S., Klein, M.P., Phelps, D.E., (1968) Chem. Phys., 48, p. 3831 Desando, M.A., Lahajnar, G., Sepe, A., (2010) J. Colloid Interface Sci., 345, p. 338 Spickermann, C., Thar, J., Lehmann, S.B.C., Zahn, S., Hunger, J., Buchner, R., Hunt, P.A., Kirchner, B., (2008) J. Chem. Phys., 129, p. 104505 Vila, J., Gines, P., Rilo, E., Cabeza, O., Varela, L.M., (2006) Fluid Phase Equilib., 247, p. 32 Bowers, J., Butts, C.P., Martin, P.J., Vergara-Gutierrez, M.C., Heenan, R.K., (2004) Langmuir, 20, p. 2191 Zhang, H.C., Liang, H.J., Wang, J.J., Li, K., (2007) Z. Phys. Chem., 221, p. 1061 Neumann, B., (2001) J. Phys. Chem. B, 105, p. 8268 Wang, Y.D., Cakmak, M., (2001) Polymer, 42, p. 4233 Korgel, B.A., Fitzmaurice, D., (1999) Phys. Rev. B: Condens. Matter Mater. Phys., 59, p. 14191 Verma, R., Marand, H., Hsiao, B., (1996) Macromolecules, 29, p. 7767 Schatzbe, P., (1967) J. Phys. Chem., 71, p. 4569 Perera, A., Sokolic, F., Zoranic, L., (2007) Phys. Rev. E: Stat., Nonlinear, Soft Matter Phys., 75, p. 060502 Barhdadi, R., Troupel, M., Comminges, C., Laurent, M., Doherty, A., (2011) J. Phys. Chem. B, 116, p. 277 Coelho, F., Eberlin, M.N., (2011) Angew. Chem., Int. Ed., 50, p. 5261 Bader, R.F.W., (1991) Chem. Rev., 91, p. 893 Bader, R.F.W., Popelier, P.L.A., Keith, T.A., (1994) Angew. Chem., Int. Ed., 33, p. 620 Bone, R.G.A., Bader, R.F.W., (1996) J. Phys. Chem., 100, p. 10892 Hernandez-Trujillo, J., Bader, R.F.W., (2000) J. Phys. Chem. A, 104, p. 1779 Bader, R.F.W., (1998) J. Phys. Chem. A, 102, p. 7314 Popelier, P.L.A., (1999) J. Phys. Chem. A, 103, p. 2883 O'Brien, S.E., Popelier, P.L.A., (1999) Can. J. Chem., 77, p. 28 Popelier, P.L.A., (1998) J. Phys. Chem. A, 102, p. 1873 Koch, U., Popelier, P.L.A., (1995) J. Phys. Chem., 99, p. 9747 Bushmarinov, I.S., Lyssenko, K.A., Antipin, M.Y., (2009) Russ. Chem. Rev., 78, p. 283