Anion nucleophilicity in ionic liquids: a comparison with traditional molecular solvents of different polarity

被引：40
作者：
Landini, D
Maia, A
机构：
[1] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy
[2] CNR, Ist ISTM, I-20133 Milan, Italy
来源：
TETRAHEDRON LETTERS | 2005年 / 46卷 / 23期
关键词：
nucleophilic substitutions; anion reactivity; ionic liquids; hydrogen bonding effect; water effect;
D O I：
10.1016/j.tetlet.2005.04.044
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The nucleophilic reactivity of a homogeneous series of anions (halides, pseudohalides and organic anions) in the ionic liquids [hexmim] [ClO4] and [hexmim] [PF6] has been measured in their reaction with n-alkyl methanesulfonates, and compared with that found in traditional molecular solvents of different polarity, that is, chlorobenzene, DMSO, and MeOH. (c) 2005 Elsevier Ltd. All rights reserved.
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页码：3961 / 3963
页数：3
相关论文
共 32 条
[1]   Key role of water for nucleophilic substitutions in phase-transfer-catalyzed processes: A mini-review [J].
Albanese, D ;
Landini, D ;
Maia, A ;
Penso, M .
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2001, 40 (11) :2396-2401
[2]   EVIDENCE FOR HYDROGEN-BONDING IN SOLUTIONS OF 1-ETHYL-3-METHYLIMIDAZOLIUM HALIDES, AND ITS IMPLICATIONS FOR ROOM-TEMPERATURE HALOGENOALUMINATE(III) IONIC LIQUIDS [J].
AVENT, AG ;
CHALONER, PA ;
DAY, MP ;
SEDDON, KR ;
WELTON, T .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1994, (23) :3405-3413
[3]   Temperature-dependent microscopic solvent properties of 'dry' and 'wet' 1-butyl-3-methylimidazolium hexafluorophosphate: correlation with ET(30) and Kamlet-Taft polarity scales [J].
Baker, SN ;
Baker, GA ;
Bright, FV .
GREEN CHEMISTRY, 2002, 4 (02) :165-169
[4]  
BIANCHI L, 2003, TETRAHEDRON LETT, V44, P2027
[5]  
BIANCHI L, 2003, TETRAHEDRON LETT, V44, P6583
[6]  
Cammarata L, 2001, PHYS CHEM CHEM PHYS, V3, P5192, DOI 10.1039/b106900d
[7]   Magnitudes and chemical consequences of R3N+-C-H•••O=C hydrogen bonding [J].
Cannizzaro, CE ;
Houk, KN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (24) :7163-7169
[8]   Electrophilic catalysis in nucleophilic substitution reactions in ionic liquids [J].
Cavazza, M ;
Pietra, F .
TETRAHEDRON LETTERS, 2004, 45 (18) :3633-3634
[9]   Nucleophilic displacement reactions in ionic liquids:: Substrate and solvent effect in the reaction of NaN3 and KCN with alkyl halides and tosylates [J].
Chiappe, C ;
Pieraccini, D ;
Saullo, P .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (17) :6710-6715
[10]   Solvent-solute interactions in ionic liquids [J].
Crowhurst, L ;
Mawdsley, PR ;
Perez-Arlandis, JM ;
Salter, PA ;
Welton, T .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2003, 5 (13) :2790-2794
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