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Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

17.0K
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...
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Conformations of Cyclohexane02:11

Conformations of Cyclohexane

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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.
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...
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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.
For example, in...
14.1K
Cycloalkanes02:28

Cycloalkanes

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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...
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Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

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Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
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Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization01:13

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2.8K
Dieckmann cyclization is an intramolecular Claisen condensation of diesters. The reaction occurs in the presence of a base and generates a cyclic β-ketoester as the final product. Commonly, 1, 6 and 1, 7-diesters are preferred substrates for the reaction since the generated five, and six-membered cyclic β-keto esters are particularly more stable.
2.8K

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Cyclobenzoin Esters as Hosts for Thin Guests.

Corie M McHale1, Lucas J Karas1, Xiqu Wang1

  • 1Department of Chemistry, University of Houston, 3585 Cullen Boulevard #112, Houston, Texas 77204-5003, United States.

Organic Letters
|February 26, 2021
PubMed
Summary
This summary is machine-generated.

Cyclotetrabenzoin esters selectively bind small molecules with triple bonds, like alkynes and nitriles. Cocrystal structures show these molecules fit snugly within the ester

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Area of Science:

  • Supramolecular chemistry
  • Organic chemistry
  • Crystal engineering

Background:

  • Cyclotetrabenzoin esters are macrocyclic compounds with potential host-guest properties.
  • Understanding molecular recognition within confined spaces is crucial for designing new materials and catalysts.

Purpose of the Study:

  • To investigate the host-guest chemistry of cyclotetrabenzoin esters with molecules containing triple bonds.
  • To elucidate the binding interactions and selectivity of these host-guest complexes.

Main Methods:

  • Cocrystallization of cyclotetrabenzoin esters with various alkynes and nitriles.
  • X-ray crystallography to determine the structures of the resulting complexes.
  • Analysis of non-covalent interactions within the crystal lattice.

Main Results:

  • Four distinct cocrystal structures were obtained, revealing the encapsulation of terminal alkynes and nitriles within the cyclotetrabenzoin cavity.
  • Favorable interactions were observed between the π-clouds of the triple bonds and the aromatic walls of the host molecule.
  • Selective binding was demonstrated for aliphatic nitriles and terminal alkynes, while aromatic counterparts remained outside the cavity.

Conclusions:

  • Cyclotetrabenzoin esters effectively host small molecules featuring triple bonds.
  • The binding is driven by specific π-π interactions and van der Waals forces within the host cavity.
  • This host-guest complexation exhibits selectivity, offering potential for molecular recognition and separation applications.