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Videos de Conceptos Relacionados

Radical Reactivity: Overview01:11

Radical Reactivity: Overview

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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...
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Radical Formation: Addition00:47

Radical Formation: Addition

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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...
1.7K
Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

1.9K
Radicals adjacent to electron‐withdrawing groups are called electrophilic radicals. These radicals readily react with nucleophilic alkenes. For example, the malonate radical, in which the radical center is flanked by two electron‐withdrawing groups, reacts readily with butyl vinyl ether, which consists of an electron‐donating oxygen substituent. The reaction between electrophilic malonate radical and nucleophilic vinyl ether is favored because the radical has a...
1.9K
Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

4.0K
This lesson delves into the geometry of a radical, which is influenced by the electronic structure of the molecule. The principle is similar to that of a lone pair, where the unpaired electron influences the geometry at the radical center.
Accordingly, the structure of a trivalent radical lies between the geometries of carbocations and carbanions. An sp2-hybridized carbocation is trigonal planar, while an sp3-hybridized carbanion is trigonal pyramidal. Here, the difference in geometry is...
4.0K
Radical Formation: Overview01:03

Radical Formation: Overview

2.1K
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...
2.1K
Radical Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

1.9K
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...
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Video Experimental Relacionado

Updated: Jun 11, 2025

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

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La polaridad radical

Jacob J A Garwood1, Andrew D Chen1, David A Nagib1

  • 1Department of Chemistry and Biochemistry, The Ohio State University, Columbus, Ohio 43210, United States.

Journal of the American Chemical Society
|October 4, 2024
PubMed
Resumen
Este resumen es generado por máquina.

Comprender la polaridad radical es clave para controlar las reacciones químicas. Este estudio cuantifica la electrophilicidad radical y la nucleophilicidad, creando una base de datos validada experimentalmente para predecir la reactividad y mejorar los resultados sintéticos.

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Last Updated: Jun 11, 2025

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Área de la Ciencia:

  • Química orgánica
  • Química computacional
  • Química Física

Sus antecedentes:

  • La polaridad intermedia radical influye significativamente en la reactividad y la selectividad en la síntesis química.
  • La predicción y cuantificación de esta influencia es crucial para el desarrollo de la reacción.

Objetivo del estudio:

  • Para calcular computacionalmente la electrophilicidad / nucleophilicidad de más de 500 radicales.
  • Para validar experimentalmente estas polaridades calculadas para una amplia gama de especies radicales.
  • Establecer un modelo predictivo que correlacione la polaridad radical con la reactividad y la selectividad.

Principales métodos:

  • Cálculos de la Teoría Funcional de la Densidad (DFT) para determinar la electrofilia/nucleofilia (ω) para más de 500 radicales.
  • Validación experimental utilizando experimentos de competencia con más de 50 radicales centrados en C, N y O.
  • Análisis de correlación entre la polaridad calculada y la reactividad relativa cuantificada (k_rel).

Principales resultados:

  • Una base de datos completa de polaridades radicales computadas para los intermedios sintéticos comunes.
  • La validación experimental confirmó altas correlaciones entre la polaridad calculada y la reactividad medida.
  • Se observó una fuerte relación entre la electrofilicidad (ω) y la reactividad relativa (k_rel), con pequeños cambios de polaridad que producen mejoras significativas de la velocidad.

Conclusiones:

  • La base de datos validada experimentalmente permite una predicción precisa de la reactividad y la selectividad de los radicales.
  • El aprovechamiento de la mejora de la velocidad ajustada a la polaridad puede optimizar el desarrollo de la reacción sintética.
  • Este recurso ayudará a solucionar problemas y diseñar nuevas vías sintéticas.