On the characterization of some [bmim][X]/co-solvent binary mixtures: a multidisciplinary approach by using kinetic, spectrophotometric and conductometric investigations

被引:51
作者
D'Anna, Francesca [1 ]
Frenna, Vincenzo [1 ]
La Marca, Sandra [1 ]
Noto, Renato [1 ]
Pace, Vitalba [1 ]
Spinelli, Domenico [2 ]
机构
[1] Univ Palermo, Dipartimento Chim Organ E Paterno, I-90128 Palermo, Italy
[2] Univ Bologna, Dipartimento Chim Organ A Mangini, I-40126 Bologna, Italy
关键词
ionic liquids; binary mixtures; MHR reaction;
D O I
10.1016/j.tet.2007.11.033
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In order to study the intrinsic characteristics and to evaluate the structural variations determined by the addition of a co-solvent to 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim][BF4]) we examined the behaviour of some probes in [bmim][BF4]/co-solvent binary mixtures. The rate constants of the piperidino-catalyzed rearrangement of the Z-phenylhydrazone of the 3-benzoyl-5-phenyl-1,2,4-oxadiazole into the relevant 4-benzoylamino-2,5-diphenyl-1,2,3-triazole as well as the spectrometric properties of pyrene and Nile Red were evaluated. With the same purpose also H-1 NMR and conductivity measurements were carried out. By comparison the behaviour of 1-butyl-3-methylimidazolium bis-(trifluoromethylsulfonylimide)/1,4-dioxane mixtures has been analyzed. The whole of data confirms the presence of weak interactions that determine a partially preorganized structure for [bmim][X]. This is perturbed at some degrees by quantity and nature of guest molecules. For example conductivity measurements support the idea that different charged aggregates are present in the [bmim] [X]/co-solvent binary mixtures. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:672 / 680
页数:9
相关论文
共 65 条
[21]   Preparation of silica aerogel using ionic liquids as solvents [J].
Dai, S ;
Ju, YH ;
Gao, HJ ;
Lin, JS ;
Pennycook, SJ ;
Barnes, CE .
CHEMICAL COMMUNICATIONS, 2000, (03) :243-244
[22]   Investigation on aggregate formation of ionic liquids [J].
Dorbritz, S ;
Ruth, W ;
Kragl, U .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (09) :1273-1279
[23]   On the solid, liquid and solution structural organization of imidazolium ionic liquids [J].
Dupont, J .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2004, 15 (03) :341-350
[24]   Physico-chemical processes in imidazolium ionic liquids [J].
Dupont, Jairton ;
Suarez, Paulo A. Z. .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2006, 8 (21) :2441-2452
[25]   New integrated measurement protocol using capillary electrophoresis instrumentation for the determination of viscosity, conductivity and absorbance of ionic liquid-molecular solvent mixtures [J].
François, Y ;
Zhang, K ;
Varenne, A ;
Gareil, P .
ANALYTICA CHIMICA ACTA, 2006, 562 (02) :164-170
[26]   MONONUCLEAR HETEROCYCLIC REARRANGEMENTS .9. A KINETIC-STUDY OF THE REARRANGEMENT OF THE Z-PHENYLHYDRAZONE OF "3-BENZOYL-5-PHENYL-1,2,4-OXADIAZOLE INTO 4-BENZOYLAMINO-2,5-DIPHENYL-1,2,3-TRIAZOLE IN METHANOL, DIOXAN, ETHYL-ACETATE, AND ACETONITRILE [J].
FRENNA, V ;
VIVONA, N ;
CONSIGLIO, G ;
SPINELLI, D .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1983, (08) :1199-1202
[27]  
Gordon CM, 2003, ACS SYM SER, V856, P357
[28]   Effects of nonionic micelles on the rate of mononuclear heterocyclic rearrangement of (Z)-phenylhydrazones of 5-substituted 3-benzoyl-1,2,4-oxadiazoles [J].
Guernelli, S ;
Noto, R ;
Sbriziolo, C ;
Spinelli, D ;
Liveri, MLT .
JOURNAL OF COLLOID AND INTERFACE SCIENCE, 2001, 239 (01) :217-221
[29]   Host-guest interactions between β-cyclodextrin and the (Z)-phenylhydrazone of 3-benzoyl-5-phenyl-1,2,4-oxadiazole:: The first kinetic study of a ring-ring interconversion in a "confined environment" [J].
Guernelli, S ;
Laganà, MF ;
Spinelli, D ;
Lo Meo, P ;
Noto, R ;
Riela, S .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (09) :2948-2953
[30]   Solvatochromic parameters for binary mixtures of 1-(1-butyl)-3-methylimidazolium tetrafluoroborate with some protic molecular solvents [J].
Harifi-Mood, AR ;
Habibi-Yangjeh, A ;
Gholami, MR .
JOURNAL OF PHYSICAL CHEMISTRY B, 2006, 110 (13) :7073-7078