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Videos de Conceptos Relacionados

Radical Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

The presence of electron-donating, electron-withdrawing, or conjugating groups adjacent to a radical center, imparts electronic stabilization to the radicals. Examples of such electronically-stabilized radicals are triphenylmethyl, tetramethylpiperidine‐N‐oxide, and 2,2‐diphenyl‐1‐picrylhydrazyl. These radicals are remarkably stable and are known as persistent radicals. Some of the persistent radicals can even be isolated and purified.
Along with electronic factors, steric factors also account...
Radical Reactivity: Overview01:11

Radical Reactivity: Overview

Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired molecule. These three...
Radical Formation: Overview01:03

Radical Formation: Overview

A bond can be broken either by heterolytic bond cleavage to form ions or homolytic bond cleavage to yield radicals. A fishhook arrow is used to represent the motion of a single electron in homolytic bond cleavage. There are two main sources from which radicals can be formed:
Radicals from spin-paired molecules:
Radicals can be obtained from spin-paired molecules either by homolysis or electron transfer. While two radicals are formed in the former, an electron is added in the latter, also known...
Radical Formation: Addition00:47

Radical Formation: Addition

Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an unpaired...
Radical Formation: Homolysis00:54

Radical Formation: Homolysis

A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.
Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak carbon–halogen...

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Exploring the Radical Nature of a Carbon Surface by Electron Paramagnetic Resonance and a Calibrated Gas Flow
10:34

Exploring the Radical Nature of a Carbon Surface by Electron Paramagnetic Resonance and a Calibrated Gas Flow

Published on: April 24, 2014

La estabilización radical inducida por la unión mecánica inducida por la unión mecánica.

Hao Li1, Zhixue Zhu, Albert C Fahrenbach

  • 1Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208-3113, United States.

Journal of the American Chemical Society
|November 21, 2012
PubMed
Resumen
Este resumen es generado por máquina.

Los investigadores sintetizaron nuevos [2] rotaxanos con cationes radicales estabilizados. Estas máquinas moleculares exhiben barreras de transporte sintonizables y potencial para materiales paramagnéticos y dispositivos conductores.

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Área de la Ciencia:

  • Química supramolecular de las moléculas.
  • Ciencia de los materiales Ciencia de los materiales.
  • Química orgánica es la química orgánica.

Sus antecedentes:

  • Los rotaxanos son moléculas mecánicamente entrelazadas con aplicaciones potenciales en dispositivos moleculares.
  • Los cationes radicales estabilizados son bloques de construcción cruciales para los materiales avanzados.
  • Las unidades de 4,4'-bipiridinium (BIPY(2+)) son componentes comunes en los sistemas redox-activos.

Objetivo del estudio:

  • Para sintetizar una serie homóloga de [2]rotaxanos con ciclobis (((paraquat-p-fenileno) (CBPQT (((4+)) y diferentes longitudes de cadena de oligometileno en 4,4'-bipiridinium (BIPY (((2+)) componentes de mancuerna.
  • Investigar las propiedades electroquímicas y la estabilidad de los cationes radicales BIPY ((•+) resultantes.
  • Para explorar la relación entre la estructura molecular y la dinámica del traslado de anillos.

Principales métodos:

  • Síntesis utilizando templación radical y reacciones de cicloadición azida-alquina sin cobre.
  • Caracterización mediante voltametría cíclica, espectroscopia UV/vis, espectrometría de masas y espectroscopia de RMN 1H.

Principales resultados:

  • Síntesis exitosa de una serie de [2]rotaxanos con cationes radicales BIPY(•+) estabilizados, resistentes a la oxidación.
  • Observación de una mayor repulsión coulombina en formas oxidadas, desestabilizando las coconformaciones del estado fundamental.
  • El más pequeño [2]rotaxano existe como monoradical bajo condiciones ambientales.
  • Aumento lineal de las barreras de energía de activación para el transporte en anillo con el aumento de la longitud de la cadena.

Conclusiones:

  • Se ha desarrollado un nuevo método para producir cationes radicales BIPY ((•+) altamente estabilizados.
  • Los rotaxanos sintetizados [2] ofrecen dinámicas moleculares sintonizables para aplicaciones potenciales.
  • Estos hallazgos abren caminos para la construcción de materiales paramagnéticos y dispositivos electrónicos moleculares conductores.