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Related Concept Videos

Prochirality02:05

Prochirality

The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
Properties of Enantiomers and Optical Activity02:24

Properties of Enantiomers and Optical Activity

It is essential to understand the difference between chiral and achiral interactions and the implications thereof in optical activity and their applications. Just as our feet, which are chiral, interact uniquely with chiral objects, such as a pair of shoes, but identically with achiral socks, enantiomers of a molecule exhibit different properties only when they interact with other chiral media. An example of a significant implication from this facet is the phenomenon known as optical activity,...
Naming Enantiomers02:21

Naming Enantiomers

The naming of enantiomers employs the Cahn–Ingold–Prelog rules that involve assigning priorities to different substituent groups at a chiral center. Each enantiomer, being a distinct molecule, is assigned a unique name by the Cahn–Ingold–Prelog (CIP) rules, also called the R–S system. The prefix R- or S- attached to the chiral centers in an enantiomer is dependent on the spatial arrangement of the four substituents on the chiral center. The R–S system essentially comprises three steps:...
¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons00:58

¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons

Replacing each alpha-hydrogen in chloroethane by bromine (or a different functional group) yields a pair of enantiomers. Such protons are called prochiral or enantiotopic and are related by a mirror plane. Enantiotopic protons are chemically equivalent in an achiral environment. Because most proton NMR spectra are recorded using achiral solvents, enantiotopic hydrogens yield a single signal.
In chiral compounds such as 2-butanol, replacing the methylene hydrogens at C3 produces a pair of...
Racemic Mixtures and the Resolution of Enantiomers02:30

Racemic Mixtures and the Resolution of Enantiomers

A racemic mixture, or racemate, is an equimolar mixture of enantiomers of a molecule that can be separated using their unique interaction with chiral molecules or media. Racemic mixtures are denoted by the (±)- prefix. This ‘optical rotation descriptor’ applies to the whole solution of a racemic mixture rather than a specific stereoisomer. Enantiomers typically have the same physical and chemical properties. Hence, they are not easily separable. However, enantiomers can exhibit different...

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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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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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Ephedrinium-based protic chiral ionic liquids for enantiomeric recognition.

Sergio L de Rooy1, Min Li, David K Bwambok

  • 1Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803, USA.

Chirality
|December 3, 2010
PubMed
Summary

Novel chiral ionic liquids derived from ephedrines show strong chiral recognition abilities. These protic chiral ionic liquids (PCILs) exhibit thermal stability and potential for enantiomeric recognition of diverse analytes.

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Published on: February 7, 2019

Area of Science:

  • Organic Chemistry
  • Materials Science
  • Analytical Chemistry

Background:

  • Protic chiral ionic liquids (PCILs) are essential for chiral separations and asymmetric synthesis.
  • Ephedrine derivatives offer a promising scaffold for designing novel chiral ionic liquids.
  • Understanding structure-property relationships in PCILs is crucial for optimizing their performance.

Purpose of the Study:

  • To synthesize and characterize novel PCILs derived from ephedrine enantiomers.
  • To investigate the influence of structural variations on the physicochemical properties of these PCILs.
  • To evaluate the chiral recognition capabilities of the synthesized PCILs.

Main Methods:

  • Synthesis of PCILs via neutralization of ephedrine derivatives with fluorinated acids.
  • Characterization using NMR, TGA, DSC, CD, MS, and elemental analysis.
  • Chiral recognition studies using (19)F-NMR and fluorescence spectroscopy.

Main Results:

  • Six novel ephedrinium-based PCILs were successfully synthesized and retained chirality.
  • PCILs exhibited thermal stability up to 220°C and glass transition temperatures between -60 and -30°C.
  • Strong chiral recognition was observed for potassium Mosher's salt and diverse analytes.

Conclusions:

  • Ephedrinium-based PCILs are promising candidates for chiral recognition applications.
  • Structural modifications significantly influence the properties and recognition abilities of PCILs.
  • These PCILs offer a versatile platform for enantioselective sensing and separation.