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Related Concept Videos

Ion Exchange01:17

Ion Exchange

Ion exchange chromatography separates charged molecules from a solution by reversibly exchanging them with mobile, or 'active', ions associated with the oppositely charged stationary phase. This method can be used to separate ions, soften and deionize water, and purify solutions. The polymers comprising the ion-exchange column are high-molecular-weight and chemically stable polymers, crosslinked to be porous and essentially insoluble. They are also functionalized with either acidic or basic...
Crown Ethers02:36

Crown Ethers

Crown ethers are cyclic polyethers that contain multiple oxygen atoms, usually arranged in a regular pattern. The first crown ether was synthesized by Charles Pederson while working at DuPont in 1967. For this work, Pedersen was co-awarded the 1987 Nobel Prize in Chemistry. Crown ethers are named using the formula x-crown-y, where x is the total number of atoms in the ring and y is the number of ether oxygen atoms. The term 'crown' refers to the crown-like shape that these ether molecules take.
Preparation of Carboxylic Acids: Hydrolysis of Nitriles01:19

Preparation of Carboxylic Acids: Hydrolysis of Nitriles

Nitriles (R–CN) can be converted into carboxylic acids (R–COOH) upon treatment with aqueous acids, i.e., upon hydrolysis of nitriles. Under base-catalyzed conditions, carboxylate anions (R–COO−) are formed.
Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
Structure and Nomenclature of Ethers02:28

Structure and Nomenclature of Ethers

Structure and Bonding
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
Classification of Ethers
Based on their attached substituent groups, ethers can be classified into two...
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.

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Related Experiment Video

Updated: May 31, 2026

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
06:31

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

Oligoether carboxylates: task-specific room-temperature ionic liquids.

Regina Klein1, Oliver Zech, Eva Maurer

  • 1Institute of Physical and Theoretical Chemistry, University of Regensburg, D-93040 Regensburg, Germany.

The Journal of Physical Chemistry. B
|June 21, 2011
PubMed
Summary
This summary is machine-generated.

New ionic liquids using oligoether carboxylates (TOTO) show improved properties. Replacing alkali ions with quaternary ammonium ions significantly lowers viscosity and enhances conductivity for TOTO-based ionic liquids.

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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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Synthesis of Ionic Liquid Based Electrolytes, Assembly of Li-ion Batteries, and Measurements of Performance at High Temperature

Published on: December 20, 2016

Area of Science:

  • Materials Science
  • Electrochemistry
  • Physical Chemistry

Background:

  • A novel family of ionic liquids based on oligoether carboxylates, specifically 2,5,8,11-Tetraoxatridecan-13-oate (TOTO), has been developed.
  • While TOTO salts with alkali ions like lithium and sodium form room-temperature ionic liquids (RTILs), they exhibit very high viscosities and low conductivities.

Purpose of the Study:

  • To investigate the properties of TOTO-based ionic liquids when alkali cations are replaced by tetraalkylammonium (TAA) ions and choline (Ch).
  • To evaluate the impact of cation choice on viscosity, conductivity, and polarity of TOTO ionic liquids.

Main Methods:

  • Synthesis and characterization of TOTO salts with tetraethylammonium (TEA), tetrapropylammonium (TPA), tetrabutylammonium (TBA), and choline (Ch) cations.
  • Measurement of viscosity, conductivity, solvent polarity, and Kamlet-Taft parameters as a function of temperature for the synthesized ionic liquids.

Main Results:

  • All synthesized TOTO salts with quaternary ammonium cations were found to be ionic liquids at ambient temperatures, with glass transition temperatures around -60 °C.
  • Compared to alkali TOTO salts, quaternary ammonium TOTO ionic liquids demonstrated over 600-fold decrease in viscosity and up to 1000-fold increase in conductivity.
  • TOTO ionic liquids with choline and TAA cations exhibited higher polarity than those with sodium ions.

Conclusions:

  • Replacing alkali cations with quaternary ammonium ions (TAA, Ch) dramatically improves the performance of TOTO-based ionic liquids, making them suitable for broader applications.
  • The enhanced properties are attributed to ion-pairing and structure-breaking effects, with potential implications for the complexation ability of the TOTO anion.