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Related Concept Videos

β-Dicarbonyl Compounds via Crossed Claisen Condensations01:18

β-Dicarbonyl Compounds via Crossed Claisen Condensations

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Crossed Claisen condensations are base-promoted reactions between two different ester molecules producing β-dicarbonyl compounds.  The reaction involving esters, with both containing α hydrogen, results in a mixture of four different products that are difficult to isolate. This reduces the synthetic utility of the reaction.
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Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization01:13

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Dieckmann cyclization is an intramolecular Claisen condensation of diesters. The reaction occurs in the presence of a base and generates a cyclic β-ketoester as the final product. Commonly, 1, 6 and 1, 7-diesters are preferred substrates for the reaction since the generated five, and six-membered cyclic β-keto esters are particularly more stable.
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Esters to β-Ketoesters: Claisen Condensation Mechanism01:08

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Regular Claisen condensation involves the synthesis of β-ketoesters by combining identical ester molecules bearing two α hydrogens in the presence of an alkoxide base. The reaction commences with the deprotonation of the acidic α hydrogen by the base to form a resonance stabilized ester enolate. This nucleophilic ion then attacks the carbonyl center of another ester molecule to generate a tetrahedral alkoxide intermediate. Next, the expulsion of the alkoxide group from the...
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Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

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Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
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Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism01:13

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Carboxylic acids react with alcohols to yield esters via an acid-catalyzed condensation reaction called Fischer esterification. This is a nucleophilic acyl substitution reaction that proceeds via a tetrahedral intermediate, where a water molecule is eliminated as the leaving group.
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Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

13.4K
This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
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Updated: Sep 27, 2025

Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction
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Host-guest interactions between oleic acid and β-cyclodextrin: A combined experimental and theoretical study.

Rui Liu1, Xiaoli Qin2, Xiong Liu2

  • 1College of Food Science, Southwest University, Chongqing 400715, China.

Food Chemistry
|April 13, 2022
PubMed
Summary

Oleic acid (OA) and β-cyclodextrin (β-CD) form a stable complex, enhancing OA

Keywords:
Density functional theory calculationHydrogen bondsInclusion complexOleic acidβ-Cyclodextrin

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Area of Science:

  • Physical Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Oleic acid (OA) is an unsaturated fatty acid prone to oxidation.
  • Beta-cyclodextrin (β-CD) is a cyclic oligosaccharide used for encapsulation.
  • Encapsulation can improve the stability and delivery of sensitive compounds.

Purpose of the Study:

  • To investigate the formation and properties of an oleic acid-β-cyclodextrin (OA/β-CD) inclusion complex.
  • To evaluate the enhanced stability of OA when complexed with β-CD.
  • To elucidate the interaction mechanisms between OA and β-CD at a molecular level.

Main Methods:

  • Experimental techniques: Differential Scanning Calorimetry (DSC), X-ray Diffraction (XRD), Raman Spectroscopy, Fourier Transform Infrared Spectroscopy (FTIR).
  • Computational methods: Conformational search, weak interactions analysis, topological analysis (Atoms in Molecules theory).

Main Results:

  • Successful formation of OA/β-CD inclusion complex confirmed by DSC and XRD.
  • Enhanced stability of OA within the β-CD complex: 61.2°C higher degradation temperature and reduced peroxide value.
  • Spectroscopic analysis indicated hydrogen bonding between OA's carboxyl group and the β-CD cavity.
  • Computational analysis revealed significant van der Waals dispersion forces and moderate hydrogen bonds contributing to complex stability.

Conclusions:

  • The OA/β-CD inclusion complex formation significantly improves the stability of oleic acid.
  • Hydrogen bonding and van der Waals interactions are key to the complex's stability.
  • This study provides a theoretical foundation for using β-CD to stabilize unsaturated fatty acids in nutritional supplements.