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Related Concept Videos

Conformations of Cyclohexane02:11

Conformations of Cyclohexane

15.2K
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...
15.2K
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

14.1K
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...
14.1K
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

17.9K
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...
17.9K
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

14.7K
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...
14.7K
Cooperative Allosteric Transitions01:58

Cooperative Allosteric Transitions

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3.0K
Cooperative Allosteric Transitions01:58

Cooperative Allosteric Transitions

8.6K
Cooperative allosteric transitions can occur in multimeric proteins, where each subunit of the protein has its own ligand-binding site. When a ligand binds to any of these subunits, it triggers a conformational change that affects the binding sites in the other subunits; this can change the affinity of the other sites for their respective ligands. The ability of the protein to change the shape of its binding site is attributed to the presence of a mix of flexible and stable segments in the...
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Designing Macrocycles to Adopt Persistent, Isoenergetic Conformations.

Liam E Claton1, Gretel A Stokes1, Annie L Downum1

  • 1Department of Chemistry & Biochemistry, Texas Christian University, Fort Worth, Texas 76129, United States.

The Journal of Organic Chemistry
|October 21, 2025
PubMed
Summary
This summary is machine-generated.

Researchers created macrocyclic dimers with stable, defined shapes using self-reactive monomers. These molecules show distinct conformations at room temperature, which merge at higher temperatures, offering a balance between flexibility and rigidity in molecular design.

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Area of Science:

  • Molecular Chemistry
  • Supramolecular Chemistry
  • Chemical Physics

Background:

  • Designing molecules with predictable structures is challenging, often involving a trade-off between flexibility and rigidity.
  • Preorganized molecular conformations offer a potential solution, bridging the gap between undefined and single-structure molecules.

Purpose of the Study:

  • To synthesize macrocyclic dimers with persistent, well-defined conformations.
  • To investigate the conformational dynamics and energy landscape of these macrocyclic dimers.

Main Methods:

  • Condensation of self-reactive monomers to form macrocyclic dimers.
  • 1H Nuclear Magnetic Resonance (NMR) spectroscopy to observe and characterize molecular conformers under varying temperatures.
  • Computational modeling (CREST) to identify and verify persistent conformations.

Main Results:

  • Quantitative synthesis of macrocyclic dimers yielding persistent, structurally defined conformers.
  • Observation of distinct conformers at ambient conditions due to hindered bond rotations (approx. 18 kcal/mol barrier).
  • Conformer interconversion and observation of a single species at elevated temperatures (approx. 75 °C).
  • Increased conformer diversity with monomer complexity and chirality.

Conclusions:

  • Macrocyclic dimers can be engineered to adopt persistent, well-defined conformations.
  • Temperature and chirality significantly influence the observed conformational landscape.
  • Computational methods support experimental findings on conformer stability and energy.