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Related Concept Videos

Conformations of Cyclohexane02:11

Conformations of Cyclohexane

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 tetrahedral value,...
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

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 staggered...
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

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...
Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers.
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...

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Reversible dimerization of [5,6]-C60O.

Dmitri Tsyboulski1, Dieter Heymann, Sergei M Bachilo

  • 1Department of Chemistry, and Center for Nanoscale Science and Technology, Rice University, 6100 Main Street, Houston, Texas 77005, USA.

Journal of the American Chemical Society
|June 10, 2004
PubMed
Summary

A newly discovered fullerene oxide isomer, [5,6]-C(60)O, readily dimerizes into C(120)O(2). This dimer can be efficiently photodissociated to regenerate the monomer, offering a stable route for [5,6]-C(60)O production.

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Area of Science:

  • Fullerene Chemistry
  • Supramolecular Chemistry
  • Photochemistry

Background:

  • The [5,6]-open isomer of C(60)O is a recently identified fullerene derivative.
  • Fullerene dimers offer unique structural and photophysical properties.

Purpose of the Study:

  • To investigate the dimerization of [5,6]-C(60)O.
  • To characterize the structure and photophysical properties of the resulting dimer, C(120)O(2).
  • To explore the photodissociation of C(120)O(2) for regenerating [5,6]-C(60)O.

Main Methods:

  • (13)C NMR spectroscopy
  • Ab initio quantum computations
  • High-performance liquid chromatography (HPLC)
  • Photophysical measurements (absorption, fluorescence, triplet lifetime)
  • Quantum yield determination for photodissociation

Main Results:

  • [5,6]-C(60)O spontaneously dimerizes to form a C(2) symmetric, nonpolar C(120)O(2) isomer linked by two sp(3)-hybridized carbon-carbon single bonds.
  • C(120)O(2) exhibits distinct absorption (peak at 329 nm, S(1)-S(0) at 704 nm) and fluorescence spectra.
  • The triplet state lifetime of C(120)O(2) is 34 ± 2 μs.
  • Photodissociation of C(120)O(2) regenerates monomeric [5,6]-C(60)O with quantum yields up to 43% at 70°C.

Conclusions:

  • The C(120)O(2) dimer serves as a stable precursor for the photolytic generation of [5,6]-C(60)O under mild conditions.
  • [5,6]-C(60)O and its dimer exist in a dynamic equilibrium controllable by external factors.
  • This fullerene adduct holds potential for specialized synthetic applications.