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Videos de Conceptos Relacionados

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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La dimerización reversible de [5,6]-C60O es el resultado de la

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
Resumen

Un isómero de óxido de fullereno recién descubierto, [5,6]-C(60) O, se dimeriza fácilmente en C(120) O(2). Este dímero puede ser fotodisociado de manera eficiente para regenerar el monómero, ofreciendo una ruta estable para la producción de [5,6]-C(60) O.

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Área de la Ciencia:

  • Química de los fullerenos.
  • Química supramolecular de las moléculas.
  • La fotoquímica es la fotoquímica.

Sus antecedentes:

  • El isómero abierto [5,6] de C(60) O es un derivado del fullereno recientemente identificado.
  • Los dímeros de fullereno ofrecen propiedades estructurales y fotofísicas únicas.

Objetivo del estudio:

  • Para investigar la dimerización de [5,6]-C(60) O.O.
  • Para caracterizar la estructura y las propiedades fotofísicas del dímero resultante, C(120) O(2).
  • Para explorar la fotodisociación de C(120) O(2) para la regeneración de [5,6]-C(60) O.

Principales métodos:

  • (13) C Espectroscopia de RMN por resonancia magnética.
  • Ab initio las computaciones cuánticas.
  • Cromatografía líquida de alto rendimiento (HPLC)
  • Las mediciones fotofísicas (absorción, fluorescencia, tiempo de vida triple)
  • Determinación del rendimiento cuántico para la fotodissociación.

Principales resultados:

  • [5,6]-C(60) O se dimeriza espontáneamente para formar un isómero C(2) simétrico y no polar C(120) O(2) unido por dos enlaces únicos carbono-carbono híbridos sp(3).
  • C(120) O(2) exhibe una absorción distinta (pico a 329 nm, S(1) -S(0) a 704 nm) y los espectros de fluorescencia.
  • El tiempo de vida en el estado triplete de C(120)O(2) es de 34 ± 2 μs.
  • La fotodisociación de C(120)O(2) regenera el monómero [5,6]-C(60)O con rendimientos cuánticos de hasta el 43% a 70°C.

Conclusiones:

  • El dímero C(120) O(2) sirve como un precursor estable para la generación fotolítica de [5,6]-C(60) O en condiciones suaves.
  • [5,6]-C(60) O y su dímero existen en un equilibrio dinámico controlable por factores externos.
  • Este adducto de fullereno tiene potencial para aplicaciones sintéticas especializadas.