Facile Synthesis of a Chiral Ionic Liquid Derived from 1-Phenylethylamine

2007 ◽  
Vol 60 (1) ◽  
pp. 64 ◽  
Author(s):  
Syed A. Ashraf ◽  
Yingpit Pornputtkul ◽  
Leon A. P. Kane-Maguire ◽  
Gordon G. Wallace
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Melting Point ◽  
Chiral Discrimination ◽  
Chiral Chromatography ◽  
Facile Synthesis ◽  
Asymmetric Syntheses ◽  
Enantiomerically Pure ◽  
Simple Route ◽  
Chiral Ionic Liquid

A simple route is described to enantiomerically pure ionic liquids derived from (+)- and (–)-1-phenylethylamine. These very low melting point (–42°C) ionic liquids, containing the bis(trifluoromethylsulfonylimide) anion, possess a wide electrochemical potential window between –2.0 and +2.0 V (versus Ag|AgCl). They show chiral discrimination between the enantiomeric forms of Mosher’s salt, suggesting their potential as media for electrochemical asymmetric syntheses or chiral chromatography.

L-Histidinium Chiral Ionic Liquid Functionalized β-Cyclodextrin as Chiral Selector in Capillary Electrophoresis

2021 ◽  
Author(s):  
Xiaofei Ma ◽  
Jingtang Li ◽  
Xiaoqi Li ◽  
Zijie Feng ◽  
Xuan Yang ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Capillary Electrophoresis ◽  
Ionic Liquids ◽  
Molecular Modeling ◽  
Chiral Separation ◽  
Chiral Selector ◽  
Chiral Discrimination ◽  
Chiral Ionic Liquid ◽  
First Time ◽  
Good Agreement

Abstract Nowadays, ionic liquids (ILs) functionalized cyclodextrins (CDs) have drawn increasing attention in chiral separation. Herein, a novel β-CD derivative functionalized by L-histidinium IL, mono-6-deoxy-6-L-histidinium-β-cyclodextrin chloride (L-HMCDCl), was synthesized for the first time and utilized for enantioseparation of nefopam and chlorphenamine in capillary electrophoresis. The L-HMCDCl exhibited superior enantioselectivity compared with native β-CD. The effect of some key parameters such as chiral selector concentration, buffer pH and applied voltage on the enantioseparation was investigated in detail. In the interest of the chiral discrimination mechanism and the enhanced enantioselectivity of L-HMCDCl, molecular modeling with AutoDock was employed to study the interaction, which was in good agreement with experimental results.

Synthesis and Characterization of Super-Molecular Ionic Liquids

2011 ◽  
Vol 197-198 ◽  
pp. 906-910
Author(s):  
Hui Ru Liu ◽  
Li Qiang Lv ◽  
Xing Chen Zhang
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Melting Point ◽  
Quantum Chemical ◽  
Organic Molecules ◽  
Raw Materials ◽  
Ammonium Thiocyanate ◽  
Molar Ratio ◽  
Molecular Ion

This study concerned a novel super-molecular ionic liquid synthesized by ammonium thiocyanate and caprolactam. The physical characters such as melting point and electric conductivity were investigated. Results showed that the melting point is -12.2°C at the molar ratio of 3:1 (caprolactam/ammonium thiocyanate), which is much lower than raw materials. The electric conductivities of synthesized ionic liquids were close to that of imidazole ILs. The structure of ionic liquid was characterized by IR,1HNMR and quantum chemical calculations. It was shown that the NH4+cation connected with caprolactam organic molecules by hydrogen bonds, leading to the forming of a super-molecular ion. The electrostatic attraction of super-molecular ion with anion was decreased because of the larger volume of super-molecular ion than original cation, thus the melting point decreased. The key properties that distinguish super-molecular ionic liquid from other ILs were the presence of supermolecular ion, which can be used to build up a hydrogen-bonded network. This type ion liquid was named as super-molecular ion liquid.

Plasmonic behavior of ionic liquid stabilized gold nanoparticles in molecular solvents

2017 ◽  
Vol 41 (21) ◽  
pp. 12989-12995 ◽  
Author(s):  
Sachin Thawarkar ◽  
Balu Thombare ◽  
Nageshwar D. Khupse
Keyword(s):  
Gold Nanoparticles ◽  
Ionic Liquid ◽  
Ionic Liquids ◽  
Surface Plasmon Resonance ◽  
Dielectric Properties ◽  
Surface Plasmon ◽  
Plasmon Resonance ◽  
Facile Synthesis ◽  
Imidazolium Ionic Liquids ◽  
Molecular Solvents

In this paper, we have demonstrated the facile synthesis of stable gold nanoparticles (AuNPs) using imidazolium ionic liquids (ImILs) as a stabilizer as well as a surfactant and their surface plasmon resonance (SPR) in different molecular solvents with varying dielectric properties.

scholarly journals Proline Based Chiral Ionic Liquids for Enantioselective Michael Reaction

2014 ◽  
Vol 2014 ◽  
pp. 1-9 ◽  
Author(s):  
Kaoru Nobuoka ◽  
Satoshi Kitaoka ◽  
Tsutomu Kojima ◽  
Yuuki Kawano ◽  
Kazuya Hirano ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Catalytic Activity ◽  
Ionic Liquids ◽  
Positive Charge ◽  
Michael Reaction ◽  
Chiral Synthesis ◽  
Chiral Catalyst ◽  
New Approach ◽  
Chiral Ionic Liquids ◽  
Chiral Ionic Liquid

Chiral ionic liquids, starting from (S)-proline, have been prepared and evaluated the ability of a chiral catalyst. In Michael reaction of trans-β-nitrostyrene and cyclohexanone, all the reactions were carried out under homogeneous conditions without any solvent except for excess cyclohexanone. The chiral ionic liquid catalyst with the positive charge delocalized bulky pyrrolidinium cation shows excellent yields (up to 92%), diastereoselectivities (syn/anti = 96/4), and enantioselectivities (up to 95% ee) and could be reused at least three times without any loss of its catalytic activity. Such results demonstrated a promising new approach for green and economic chiral synthesis by using the chiral ionic liquids as a chiral catalyst and a chiral medium.

scholarly journals Tuning the melting point of selected ionic liquids through adjustment of the cation's dipole moment

2020 ◽  
Vol 22 (21) ◽  
pp. 12301-12311 ◽  
Author(s):  
Brooks D. Rabideau ◽  
Mohammad Soltani ◽  
Rome A. Parker ◽  
Benjamin Siu ◽  
E. Alan Salter ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Dipole Moment ◽  
Melting Point ◽  
Fluorine Substitution

Adjusting the dipole moment of an ionic liquid cation through fluorine substitution for hydrogen tunes the melting point.

scholarly journals Organic Reactions in Ionic Liquids: Ionic Liquid-accelerated Facile Synthesis of 3-alkyl-2,4-thiazolidinediones

2005 ◽  
Vol 2005 (8) ◽  
pp. 492-494 ◽  
Author(s):  
De-Hong Yang ◽  
Ben-Yong Yang ◽  
Zhen-Chu Chen ◽  
Song-Ying Chen ◽  
Qin-Guo Zheng
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Room Temperature ◽  
Room Temperature Ionic Liquid ◽  
Organic Reactions ◽  
Green Solvent ◽  
Facile Synthesis ◽  
Rate Enhancement ◽  
Significant Rate

The room temperature ionic liquid [bmim]PF6 is a new green solvent for the N-alkylation of 2,4-thiazolidinones. Significant rate enhancement and improved yields have been observed.

Towards a Better Understanding of 'Delocalized Charge' in Ionic Liquid Anions

2007 ◽  
Vol 60 (1) ◽  
pp. 15 ◽  
Author(s):  
Ekaterina I. Izgorodina ◽  
Maria Forsyth ◽  
Douglas R. MacFarlane
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Melting Point ◽  
Proton Affinity ◽  
Molten Salts ◽  
Charge Delocalization ◽  
Range Of Values

One of the main characteristics that are attributed to ionic liquids (especially those with a low melting point) is that the anions comprising the ionic liquids possess a certain degree of charge delocalization as compared to anions in traditional molten salts. Based on the proton affinity equilibrium we proposed a new energetic criterion that can be used as a measure of charge delocalization. The proposed proton affinity comparison quantifies the extent to which ionic liquid anions are delocalized. Thus it should lead to a better understanding towards the design of task-specific ionic liquids. Therefore, this criterion can be applied to newly designed anions to assure that the extent of charge delocalization falls within the same range of values on the proton affinity scale as other commonly used ionic liquid anions.

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