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Videos de Conceptos Relacionados

Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

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 low‐energy SOMO, which interacts...
Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

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...
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
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 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: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For instance, consider...

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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
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Es un catión cristalino del radical fosfinilo.

Olivier Back1, Mehmet Ali Celik, Gernot Frenking

  • 1UCR-CNRS Joint Research Chemistry Laboratory (UMI 2957), Department of Chemistry, University of California, Riverside, California 92521-0403, USA.

Journal of the American Chemical Society
|July 29, 2010
PubMed
Resumen

Los investigadores crearon un catión radical estable centrado en el fósforo a partir de un fosfaalqueno. Esta especie única, estable en soluciones y estados sólidos, fue caracterizada mediante difracción de rayos X, ofreciendo información sobre la química de los radicales de fósforo.

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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
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Área de la Ciencia:

  • Química de los organofosforados Química de los organofosforados
  • Química Radical La Química Radical es una ciencia
  • Química de los carbenos La química de los carbenos

Sus antecedentes:

  • Los fosfalicenos son compuestos insaturados que contienen un enlace doble fósforo-carbono.
  • Los carbenos cíclicos (alquilo) son versátiles ligandos y precursores en la química organometálica.
  • Los cationes de radicales estables son valiosos intermediarios en la síntesis química y en los estudios mecanicistas.

Objetivo del estudio:

  • Para sintetizar y caracterizar un nuevo y estable catión radical centrado en el fósforo.
  • Para investigar la estructura electrónica y la estabilidad de las especies radicales catiónicas.
  • Explorar el potencial de los fosfaalquenos como precursores de las especies radicales estables.

Principales métodos:

  • Oxidación de un electrón de un precursor del fosfaliceno.
  • Aislamiento y caracterización del catión radical resultante en disolución y estado sólido.
  • Análisis de difracción de rayos X monocristalino para determinar la estructura molecular.

Principales resultados:

  • Un fosfaalqueno fácilmente disponible fue oxidado con éxito a un catión radical estable centrado en el fósforo.
  • El catión radical exhibió una estabilidad indefinida tanto en la solución como en los estados sólidos.
  • La difracción de rayos X confirmó la estructura del catión radical estable, revelando sus propiedades electrónicas.

Conclusiones:

  • El estudio demuestra la viabilidad de generar cationes radicales centrados en el fósforo indefinidamente estables a partir de fosfalicenos.
  • Las especies caracterizadas se pueden ver como un radical fosfinilo con un sustituto catiónico o un radical fosfeniumilo estabilizado con carbenos.
  • Este trabajo amplía la comprensión de los intermediarios reactivos de fósforo y su estabilización.