Synthesis of Chiral Room Temperature Ionic Liquids from Amino Acids - Application in Chiral Molecular Recognition

被引：57

作者：

Gonzalez, Laura ^{[1
]}

Altava, Belen ^{[1
]}

Bolte, Michael ^{[2
]}

Burguete, M. Isabel ^{[1
]}

Garcia-Verdugo, Eduardo ^{[1
]}

Luis, Santiago V. ^{[1
]}

机构：

[1] Univ Jaume 1, Dept Inorgan & Organ Chem, Castellon de La Plana 12070, Spain

[2] Goethe Univ Frankfurt, Inst Anorgan Chem, D-60438 Frankfurt, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 26期

关键词：

Ionic liquids; Chiral shift agents; Amino acids; Carboxylic acids; Molecular recognition; CENTER-DOT-O; PHYSICOCHEMICAL PROPERTIES; IMIDAZOLIUM SALTS; HYDROGEN-BONDS; VIBRATIONAL-SPECTRA; MAGNETIC-RESONANCE; SOLVENT PROPERTIES; PHASE-TRANSITIONS; RAMAN MICROSCOPY; WATER;

D O I：

10.1002/ejoc.201200607

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of structurally new room temperature chiral ionic liquids based on an imidazolium group and derived from natural amino acids have been synthesized and studied as chiral shift agents for the chiral discrimination of enantiomeric carboxylate salts. This family of imidazolium salts can be prepared by a simple synthetic approach and most of the components are liquid at room temperature. The solid to liquid transformation temperatures can be as low as 49 degrees C. The analysis of the supramolecular structure of the resulting CILs can be used advantageously to understand the potential for the selective recognition of different hosts.

引用

页码：4996 / 5009

页数：14

共 120 条

[1] Synthesis of new chiral imidazolium salts derived from amino acids: their evaluation in chiral molecular recognition [J].

Altava, Belen ;

Barbosa, Dalgi S. ;

Isabel Burguete, M. ;

Escorihuela, Jorge ;

Luis, Santiago V. .

TETRAHEDRON-ASYMMETRY, 2009, 20 (09) :999-1003

[2] Thermophysical Properties of Pure Ionic Liquids: Review of Present Situation [J].

Aparicio, Santiago ;

Atilhan, Mert ;

Karadas, Ferdi .

INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2010, 49 (20) :9580-9595

[3] 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

[4] Magnetic resonance spectroscopy in ionic liquids [J].

Bankmann, Dennis ;

Giernoth, Ralf .

PROGRESS IN NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY, 2007, 51 (01) :63-90

[5] Synthesis of chiral ionic liquids from natural amino acids [J].

Bao, WL ;

Wang, ZM ;

Li, YX .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (02) :591-593

[6] Chiral ionic liquids, a renewal for the chemistry of chiral solvents?: Design, synthesis and applications for chiral recognition and asymmetric synthesis [J].

Baudequin, C ;

Brégeon, D ;

Levillain, J ;

Guillen, F ;

Plaquevent, JC ;

Gaumont, AC .

TETRAHEDRON-ASYMMETRY, 2005, 16 (24) :3921-3945

[7] Ionic liquids and chirality: opportunities and challenges [J].

Baudequin, C ;

Baudoux, J ;

Levillain, J ;

Cahard, D ;

Gaumont, AC ;

Plaquevent, JC .

TETRAHEDRON-ASYMMETRY, 2003, 14 (20) :3081-3093

[8] Design and synthesis of novel ionic liquid/liquid crystals (IL 2Cs) with axial chirality [J].

Baudoux, J ;

Judeinstein, P ;

Cahard, D ;

Plaquevent, JC .

TETRAHEDRON LETTERS, 2005, 46 (07) :1137-1140

[9] Efficient macrocyclization of U-turn preorganized peptidomimetics:: The role of intramolecular H-bond and solvophobic effects [J].

Becerril, J ;

Bolte, M ;

Burguete, MI ;

Galindo, F ;

García-España, E ;

Luis, SV ;

Miravet, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (22) :6677-6686

[10] Ionic liquids as modulators of the critical micelle concentration of sodium dodecyl sulfate [J].

Beyaz, A ;

Oh, WS ;

Reddy, VP .

COLLOIDS AND SURFACES B-BIOINTERFACES, 2004, 35 (02) :119-124

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