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Related Concept Videos

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...
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...
Stereochemical Effects of Enolization01:12

Stereochemical Effects of Enolization

The chiral α-carbon of the carbonyl compound is the stereocenter of the molecule. As shown in the figure below, when such a carbonyl compound undergoes racemization under an acidic or basic condition, an achiral enol is formed.
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
Radical Halogenation: Stereochemistry01:33

Radical Halogenation: Stereochemistry

Stereochemistry is the study of the different spatial arrangements of atoms in a given molecule. The stereochemistry of radical halogenations can be understood from three different situations:
Halogenation to form a new chiral center:
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...

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Related Experiment Video

Updated: Jun 6, 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

Towards racemizable chiral organogelators.

Jian Bin Lin1, Debarshi Dasgupta, Seda Cantekin

  • 1Functional Organic Materials and Devices and Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, PO Box 513, 5600MB Eindhoven, The Netherlands. j.b.lin@tue.nl

Beilstein Journal of Organic Chemistry
|November 19, 2010
PubMed
Summary

A novel chiral organogelator self-assembles into bundle fibrils in apolar solvents, forming organogels at higher concentrations. This molecule can be racemized using the base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).

Keywords:
chiralityorganogelsracemizationself-assembly

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The Synthesis of RGD-functionalized Hydrogels as a Tool for Therapeutic Applications
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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Organic Chemistry

Background:

  • Chiral organogelators are crucial for developing advanced functional materials.
  • Understanding self-assembly mechanisms is key to designing novel gelators.
  • Control over chirality and racemization is important for material properties.

Purpose of the Study:

  • To synthesize and characterize a new chiral organogelator.
  • To investigate its self-assembly behavior in apolar solvents.
  • To explore the racemization of the enantiomerically pure organogelator.

Main Methods:

  • Synthesis of the chiral organogelator.
  • Field emission scanning and transmission electron microscopy (FEG-SEM/TEM) for morphology analysis.
  • Nuclear Magnetic Resonance (¹H NMR) spectroscopy to study intermolecular interactions.
  • Chiral High-Performance Liquid Chromatography (CHPLC) to monitor racemization.

Main Results:

  • The synthesized chiral organogelator self-assembles into bundle fibrils.
  • These fibrils effectively gelate apolar solvents at higher concentrations.
  • ¹H NMR confirmed hydrogen-bonding interactions between peptide head groups.
  • Chiral HPLC demonstrated successful racemization of the organogelator using DBU.

Conclusions:

  • A novel chiral organogelator capable of forming organogels through fibril self-assembly has been developed.
  • The study highlights the role of hydrogen bonding in the gelation process.
  • The organogelator's ability to undergo base-induced racemization offers potential for dynamic material applications.