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Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

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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.
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Chair Conformation of Cyclohexane02:02

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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.
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Conformations of Cyclohexane02:11

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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.
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Conformations of Cycloalkanes02:29

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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...
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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.
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Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

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Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Metastable doubly threaded [3]rotaxanes with a large macrocycle.

Jerald E Hertzog1, Vincent J Maddi1, Laura F Hart2

  • 1Department of Chemistry, University of Chicago Chicago IL 60637 USA stuartrowan@uchicago.edu.

Chemical Science
|June 3, 2022
PubMed
Summary
This summary is machine-generated.

Researchers synthesized large, metastable doubly threaded [3]rotaxanes using a macrocycle and metal templating. Stopper group size controlled degradation rates, from minutes to months.

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science

Background:

  • Ring size is crucial for interlocked molecule dynamics.
  • Large macrocycles are key to novel molecular architectures.

Purpose of the Study:

  • To synthesize metastable doubly threaded [3]rotaxanes using a large macrocycle.
  • To investigate the impact of stopper groups on rotaxane stability.

Main Methods:

  • Synthesis of a large ditopic macrocycle and linear components.
  • Metal templating (iron(II)) for self-assembly.
  • Azide-alkyne cycloaddition for stopper installation.
  • Demetallation and characterization (NMR, MS, SEC, simulations).

Main Results:

  • High yield synthesis (65-75%) of metastable doubly threaded [3]rotaxanes.
  • Stopper group variation enabled tunable stability (half-life <1 min to ~6 months).
  • Successful characterization of large, complex interlocked structures.

Conclusions:

  • Demonstrated feasibility of synthesizing large doubly threaded [3]rotaxanes.
  • Established a method for controlling degradation rates via stopper design.
  • Opened possibilities for advanced interlocked materials with tunable properties.