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Related Concept Videos

Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this staggered...
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal tetrahedral value,...
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

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...
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3  hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that was based on the...
Cycloalkanes02:28

Cycloalkanes

Cycloalkanes are saturated cyclic hydrocarbons with carbon atoms arranged in the form of rings. They have two fewer hydrogen atoms than the corresponding acyclic alkane; therefore, their general formula is CnH2n. The structural formulas of cycloalkanes are simplified using the line-angle representation. The regular polygons are used to represent the cycloalkane rings, with each side representing a carbon-carbon bond.
The IUPAC nomenclature of cycloalkanes follows similar rules that apply to...
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...

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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
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Bistable cucurbituril rotaxanes without stoppers.

Mantosh K Sinha1, Ofer Reany, Maayan Yefet

  • 1Schulich Faculty of Chemistry, Technion - Israel Institute of Technology, Haifa, Israel.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|March 22, 2012
PubMed
Summary

Bistable rotaxanes, crucial for molecular devices, exhibit two stable binding modes. Researchers detailed their properties and reactivity, revealing a stable rotaxane without bulky end groups.

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science

Background:

  • Bistable rotaxanes are key components in molecular devices like drug delivery systems and sensors.
  • Understanding their binding modes and stability is crucial for designing advanced molecular machinery.

Purpose of the Study:

  • To investigate the structural, dynamic, and reactivity properties of cucurbit[6]uril and 1,4-bis(alkylaminomethyl)benzene host-guest complexes.
  • To characterize the two stable binding modes and the barrier between them.
  • To explore the chemical reactivity of these complexes, particularly in click chemistry.

Main Methods:

  • Nuclear Magnetic Resonance (NMR) spectroscopy
  • X-ray crystallography
  • Isothermal Titration Microcalorimetry (ITC)

Main Results:

  • Two stable binding modes were identified with a high energy barrier.
  • A 2:1 complex formed at room temperature is a kinetic product.
  • A thermodynamically stable 1:1 rotaxane, lacking bulky end groups, is formed upon heating to 100°C.

Conclusions:

  • The cucurbit[6]uril/1,4-bis(alkylaminomethyl)benzene system forms a highly stable rotaxane.
  • The study reveals insights into the kinetic and thermodynamic control of rotaxane formation and stability.
  • This work contributes to the development of novel molecular devices with tunable properties.