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Videos de Conceptos Relacionados

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

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Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
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Aromatic Compounds: Overview01:25

Aromatic Compounds: Overview

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In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday isolated...
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Basicity of Aromatic Amines01:18

Basicity of Aromatic Amines

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The basicity of aromatic amines is much weaker than that of aliphatic amines due to the involvement of the lone pair of electrons over the N atom in resonance with the aryl rings. Generally, the electron-donating ability of any substituents on the aryl ring of aromatic amines increases the basicity of the amine by increasing electron density, and hence the availability of lone pair on the nitrogen. On the other hand, electron-withdrawing functional groups on the aryl ring of amines decrease the...
8.0K
Nomenclature of Aromatic Compounds with a Single Substituent01:23

Nomenclature of Aromatic Compounds with a Single Substituent

9.9K
Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
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Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

5.3K
Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
5.3K
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

4.6K
Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
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Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
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Una dicción de tetrasilaciclobutadieno aromático estable

Xiaofei Sun1, Thomas Simler1, Ravi Yadav1

  • 1Institut für Anorganische Chemie, Karlsruher Institut für Technologie (KIT) , Engesserstrasse 15 , 76131 Karlsruhe , Germany.

Journal of the American Chemical Society
|September 12, 2019
PubMed
Resumen

Los investigadores sintetizaron y caracterizaron el primer análogo de silicio de la dicatión aromática de ciclobutadieno. Esta nueva dication de tetrasilaciclobutadieno de 2π electrones exhibe una geometría cuadrada plana, lo que confirma su aromaticidad.

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Área de la Ciencia:

  • Química del silicio orgánico
  • Estudios de aromatización
  • Síntesis inorgánica

Sus antecedentes:

  • Los dications del cyclobutadiene son sistemas aromáticos fundamentales, pero sus análogos del silicio permanecen elusivos.
  • Comprender el papel del silicio en la aromaticidad proporciona información sobre las estructuras de enlace y electrónicas.

Objetivo del estudio:

  • Sintetizar y caracterizar el primer análogo a base de silicio de la dication aromática del ciclobutadieno.
  • Investigar las propiedades estructurales y electrónicas de este nuevo grupo de silicio.

Principales métodos:

  • Una síntesis sencilla que incluye [LSiCl], [LSISiL] y NaBPh4.
  • Caracterización completa, incluida la determinación de la estructura molecular.
  • Cálculos teóricos para apoyar la interpretación de la estructura electrónica.

Principales resultados:

  • Aislamiento y caracterización exitosos de la dicción de tetrasilaciclobutadieno, [(LSi) 4)
  • La estructura revela un anillo de Si4 de cuatro miembros con una geometría casi cuadrada.
  • Los cálculos teóricos confirman un sistema aromático de 2π-electrones con un estado básico singular.

Conclusiones:

  • Se ha sintetizado el primer análogo de silicio de una dication aromática de ciclobutadieno.
  • El compuesto exhibe una aromaticidad clásica de 2π, ampliando el alcance de los sistemas aromáticos.
  • Este trabajo abre nuevas vías para explorar compuestos aromáticos a base de silicio.