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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
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

18.0K
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...
18.0K
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
Conformations of Butane02:20

Conformations of Butane

17.6K
Unlike ethane and propane that have only two major conformations, butane has more than two conformers. The staggered form of butane in which the bulky methyl groups on the two carbons are placed on opposite sides, that is, at a dihedral angle of 180°, is the lowest energy, most stable form — called the anti conformer. This conformation is stabilized due to the absence of steric repulsion between the largely spaced out methyl groups. The other two staggered conformations are...
17.6K
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
Conformations of Ethane and Propane02:18

Conformations of Ethane and Propane

16.8K
In an organic molecule, free rotation about the carbon-carbon single bond results in energetically different conformers of the molecule. Due to this rotation, called the internal rotation, ethane has two major conformations — staggered and eclipsed.
Staggered conformation is a low energy and more stable conformation with the C-H bonds on the front carbon placed at 60°dihedral angles relative to the C-H bonds on the back carbon, leading to a reduced torsional strain. In staggered...
16.8K

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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
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Templating conformations with cucurbiturils.

Nathan A Thompson1, Héctor Barbero1, Eric Masson1

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Chemical Communications (Cambridge, England)
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Two Cucurbit[8]uril macrocycles stabilize trans and cis conformations of substituted dithiophenes. Rigid naphthalene scaffolds and platinum terpyridyl groups facilitate these stable structures through specific interactions.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Coordination Chemistry

Background:

  • Stabilizing specific molecular conformations is crucial for controlling chemical properties and functions.
  • Macrocyclic hosts like Cucurbit[8]uril (CB[8]) are known for their ability to bind guest molecules and influence their behavior.
  • Dithiophene derivatives are important building blocks in materials science, but controlling their conformational flexibility can be challenging.

Purpose of the Study:

  • To investigate the stabilization of trans- and cis-conformations of 5,5'-substituted 2,2'-dithiophenes.
  • To explore the use of Cucurbit[8]uril (CB[8]) macrocycles in conjunction with rigid naphthalene scaffolds for conformational control.
  • To understand the role of platinum(II) terpyridyl substituents in mediating these conformational effects.

Main Methods:

  • Synthesis of 5,5'-substituted 2,2'-dithiophenes bearing platinum(II) terpyridyl groups with CB[8]-binding sites.
  • Utilizing rigid 2,6- and 2,7-substituted naphthalene units to mimic dithiophene conformations.
  • Employing Cucurbit[8]uril (CB[8]) macrocycles to bind and stabilize the dithiophene structures.
  • Characterization of the resulting supramolecular assemblies using spectroscopic and structural techniques.

Main Results:

  • Successful stabilization of both trans- and cis-conformations of the 5,5'-substituted 2,2'-dithiophenes was achieved.
  • The rigid naphthalene scaffolds effectively mimicked the respective trans and cis conformations.
  • Cucurbit[8]uril (CB[8]) macrocycles played a key role in securing these conformations.
  • Pt(II) terpyridyl groups, through Pt-Pt and dispersive interactions, facilitated the formation of supramolecular dimers in the presence of CB[8].

Conclusions:

  • This study demonstrates a novel strategy for controlling the conformation of dithiophene derivatives using supramolecular host-guest chemistry.
  • The combination of CB[8] macrocycles, rigid naphthalene linkers, and Pt(II) terpyridyl units provides a versatile platform for designing conformationally locked molecules.
  • These findings have implications for the development of new functional materials where precise control over molecular geometry is essential.