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Related Concept Videos

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.
Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
Drug-Receptor Bonds01:25

Drug-Receptor Bonds

Drug-receptor bonds are formed through various chemical forces when drugs interact with target cells. Covalent bonds, strong and irreversible, are exemplified by DNA-alkylating anticancer agents that inhibit cell division. However, such irreversible drug binding lacks selectivity and can modify the DNA of the surrounding healthy cells. Covalent binding often contributes to tissue toxicity, as seen with chloroform and paracetamol metabolites binding to the liver, causing hepatotoxicity.
In...
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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 22, 2026

Development of Inhibitors of Protein-protein Interactions through REPLACE: Application to the Design and Development Non-ATP Competitive CDK Inhibitors
10:33

Development of Inhibitors of Protein-protein Interactions through REPLACE: Application to the Design and Development Non-ATP Competitive CDK Inhibitors

Published on: October 26, 2015

Toward engineering intra-receptor interactions into bis(crown ethers).

Martin R Krause1, Stefan Kubik

  • 1Fachbereich Chemie-Organische Chemie, Erwin-Schrödinger-Strasse, Technische Universität Kaiserslautern, D-67663 Kaiserslautern, Germany.

Natural Product Communications
|May 2, 2012
PubMed
Summary
This summary is machine-generated.

Synthetic receptors with crown ether moieties were studied. Despite potential internal hydrophobic interactions, both receptor types bound potassium ions equally, showing enthalpy-entropy compensation effects.

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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

Area of Science:

  • Supramolecular chemistry
  • Host-guest chemistry
  • Synthetic receptor design

Background:

  • Crown ethers are known for selective ion binding.
  • Hydrophobic interactions can stabilize molecular complexes.
  • Investigating internal interactions within synthetic receptors is crucial for understanding binding thermodynamics.

Purpose of the Study:

  • To design and synthesize a bis(crown ether) receptor capable of cooperative ion binding.
  • To investigate the role of hydrophobic interactions between non-binding substituents in complex stability.
  • To elucidate the thermodynamic contributions of intra-receptor interactions to alkali metal ion binding.

Main Methods:

  • Synthesis of two diastereoisomeric bis(crown ether) compounds.
  • Isothermal titration calorimetry (ITC) for binding studies.
  • Binding affinity, enthalpy, and entropy measurements for potassium ion complexation in various solvents.

Main Results:

  • Both diastereoisomers exhibited identical overall binding affinities for potassium ions.
  • Significant differences in binding enthalpies and entropies were observed between the isomers.
  • Thermodynamic data suggest the presence of intra-receptor hydrophobic interactions in one isomer, counteracted by enthalpy-entropy compensation.

Conclusions:

  • Cooperative binding in bis(crown ether) systems can induce conformational changes leading to secondary interactions.
  • Enthalpy-entropy compensation plays a significant role in modulating binding thermodynamics, masking the effect of favorable secondary interactions on overall affinity.
  • The study highlights the complex interplay between direct host-guest interactions and indirect intra-receptor effects in synthetic receptor design.