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Videos de Conceptos Relacionados

Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...
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: Elimination00:51

Radical Formation: Elimination

Another method of radical formation is the elimination process. It is the opposite of the addition route and is driven by the instability of the radical. For example, as depicted in Figure 1, dibenzoyl peroxide yields a pair of unstable radicals upon homolysis. Given its instability, this radical spontaneously undergoes elimination via a C–C bond cleavage to form a relatively more stable phenyl radical. The mechanism involves cleavage of the bond between the α and β positions with respect to...
Acidity and Basicity of Alcohols and Phenols02:36

Acidity and Basicity of Alcohols and Phenols

Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
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.

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Video Experimental Relacionado

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Computation of Atmospheric Concentrations of Molecular Clusters from ab initio Thermochemistry
12:11

Computation of Atmospheric Concentrations of Molecular Clusters from ab initio Thermochemistry

Published on: April 8, 2020

El complejo del radical fenoxilo-agua - un aislamiento de matriz y estudio computacional.

Wolfram Sander1, Saonli Roy, Iakov Polyak

  • 1Lehrstuhl für Organische Chemie II, Ruhr-Universität Bochum, D-44801 Bochum, Germany. wolfram.sander@rub.de

Journal of the American Chemical Society
|April 10, 2012
PubMed
Resumen

Los investigadores generaron el radical fenoxilo y estudiaron su interacción con el agua en matrices de argón. Identificaron un complejo OH··O, ofreciendo información sobre sistemas biológicos como la interacción del radical tirosilo con el agua.

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Área de la Ciencia:

  • Química Física es la química física.
  • La espectroscopia es una técnica de espectroscopia.
  • Química computacional es la química computacional.

Sus antecedentes:

  • Los radicales fenoxilo son intermediarios clave en varias reacciones químicas.
  • La comprensión de las interacciones entre los radicales y el agua es crucial para los procesos biológicos.

Objetivo del estudio:

  • Para caracterizar la interacción entre el radical fenoxilo y el agua.
  • Para investigar la estabilidad de complejos radical-agua en matrices de baja temperatura.

Principales métodos:

  • Pirólisis en vacío de flash del éter fenílico alilo para generar el radical fenoxilo.
  • Productos de captura en matrices de argón a 3 K.
  • Espectroscopia infrarroja (IR) para la caracterización compleja.
  • Teoría funcional de la densidad (DFT) y cálculos QM/MM.

Principales resultados:

  • Se lograron altos rendimientos del radical fenoxilo.
  • Un complejo OH··O entre el radical fenoxilo y el agua fue identificado y caracterizado por espectroscopia IR.
  • Los isótopos confirmaron la compleja estructura.
  • No se observaron otros dímeros en condiciones experimentales.
  • Los cálculos QM/MM indicaron la inestabilidad de los complejos OH···π.

Conclusiones:

  • El complejo OH··O es el producto de interacción primario entre el radical fenoxilo y el agua en matrices de argón.
  • Los hallazgos sugieren modos específicos de unión relevantes para los sistemas biológicos.
  • La inestabilidad de los complejos OH···π tiene implicaciones para la comprensión de las interacciones entre el radical tirosilo y el agua en las proteínas.