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Related Concept Videos

Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

17.6K
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...
17.6K
¹H NMR of Conformationally Flexible Molecules: Temporal Resolution00:52

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

1.2K
At room temperature, the chair conformer of cyclohexane undergoes rapid ring flipping between two equivalent chair conformers at a rate of approximately 105 times per second. These two chair conformers are in equilibrium. The rapid ring flipping results in the interconversion of the axial proton to an equatorial proton and an equatorial to the axial proton. Such interconversions are too rapid and cannot be detected on the NMR timescale. Hence, the NMR spectrometer cannot distinguish between the...
1.2K
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

14.9K
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...
14.9K
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

3.5K
The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.
3.5K
Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

3.7K
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...
3.7K
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

13.8K
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...
13.8K

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Interactive Molecular Model Assembly with 3D Printing
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Conformationally adaptive macrocycles with flipping aromatic sidewalls.

Xiaoping Wang1, Fei Jia2, Liu-Pan Yang1

  • 1Shenzhen Grubbs Institute, Guangdong Provincial Key Laboratory of Catalysis, and Department of Chemistry, Southern University of Science and Technology, Shenzhen, 518055, China. jiangw@sustech.edu.cn.

Chemical Society Reviews
|May 28, 2020
PubMed
Summary

Conformationally adaptive macrocycles offer enhanced binding by utilizing multiple conformations. These adaptable molecules show promise in areas like chirality sensing and molecular switches.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Materials Science

Background:

  • Conformationally adaptive macrocycles exhibit dynamic behavior through rapid aromatic sidewall flipping.
  • These macrocycles integrate the binding capabilities of their various conformational states.

Purpose of the Study:

  • To review recent advancements in conformationally adaptive macrocycles.
  • To highlight the unique properties and applications of these macrocycles, particularly in the authors' research.

Main Methods:

  • Exploration of macrocycle conformational dynamics.
  • Investigation of guest binding mechanisms and affinity.
  • Analysis of responsiveness to environmental stimuli (temperature, solvent).

Main Results:

  • Macrocycles select specific conformations or combinations for maximized binding affinity.
  • The conformational network demonstrates responsiveness to temperature and solvent changes.
  • Demonstrated utility in chirality sensing, stimuli-responsive self-assembly, and molecular switches.

Conclusions:

  • Conformationally adaptive macrocycles possess unique and tunable properties.
  • These macrocycles show significant potential for future applications in supramolecular chemistry.
  • Further research is warranted to fully exploit their capabilities.