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NMR Spectroscopy of Benzene Derivatives01:37

NMR Spectroscopy of Benzene Derivatives

Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling constants depend...
Electrophilic Aromatic Substitution: Sulfonation of Benzene01:22

Electrophilic Aromatic Substitution: Sulfonation of Benzene

Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.
Structure of Benzene: Kekulé Model01:07

Structure of Benzene: Kekulé Model

In 1865, August Kekule suggested the structure of benzene according to the structural theory of organic chemistry based on the three assertions—formula of benzene is C6H6, all the hydrogens of benzene are equivalent, and each carbon must have four bonds due to its tetravalency.
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.
Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.

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Updated: Jun 21, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

Dímero de benceno protonado: un estudio experimental y ab initio.

Shamik Chakraborty1, Reza Omidyan, Ivan Alata

  • 1Centre Laser de l'Universite Paris Sud (EA. 4127), Bat. 106, Univ. Paris-Sud 11 - 91405 Orsay Cedex, France.

Journal of the American Chemical Society
|July 23, 2009
PubMed
Resumen

El dimero de benceno protonado.

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Área de la Ciencia:

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

Sus antecedentes:

  • El dimero de benceno exhibe una absorción de rayos UV.
  • La protonación altera significativamente las propiedades electrónicas.

Objetivo del estudio:

  • Para investigar el espectro de excitación del dimero de benceno protonado.
  • Para entender el desplazamiento espectral en comparación con el dimero de benceno neutro.

Principales métodos:

  • Espectro de excitación registrado en el rango de 415-600 nm.
  • Se realizan cálculos ab initio.

Principales resultados:

  • La absorción observada se extiende hasta la región visible.
  • Se identificó un desplazamiento al rojo espectral significativo en comparación con el dímero neutro.
  • Los cálculos ab initio sugieren estados excitados de transferencia de carga.

Conclusiones:

  • La protonación induce un gran desplazamiento bathocrómico en el espectro del dímero de benceno.
  • Las transiciones electrónicas en el dímero protonado se atribuyen al carácter de transferencia de carga.