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Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

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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...
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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).
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The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.
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Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
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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...
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Dissociative Electron Attachment to Hexachlorobenzene.

Alexey A Goryunkov1, Nail L Asfandiarov2, Rustam G Rakhmeev2

  • 1Chemistry Department, Lomonosov Moscow State University, Leninskie Gory, 1-3, 119991, Moscow, Russia.

Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry
|March 14, 2022
PubMed
Summary

Hexachlorobenzene gas molecules were studied using dissociative electron attachment spectroscopy. Researchers identified three decay channels for negative ions, revealing temperature-dependent behaviors and a higher electron affinity than predicted.

Keywords:
cyclic voltammetrydissociative electron attachmentelectron affinityhexachlorobenzenemass spectrometry

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Area of Science:

  • Physical Chemistry
  • Spectroscopy
  • Molecular Physics

Background:

  • Hexachlorobenzene (C6Cl6) is a persistent organic pollutant.
  • Understanding its electron interaction is crucial for environmental and chemical applications.
  • Previous studies have explored its properties, but gas-phase electron dynamics require further investigation.

Purpose of the Study:

  • To investigate the gas-phase molecular negative ions of hexachlorobenzene.
  • To identify and characterize the decay channels of these ions.
  • To determine the adiabatic electron affinity of hexachlorobenzene and compare it with theoretical predictions.

Main Methods:

  • Dissociative Electron Attachment Spectroscopy (DEAS) was employed.
  • Analysis of molecular negative ion decay pathways.
  • Application of the Arrhenius model for electron affinity estimation.

Main Results:

  • Three distinct decay channels for molecular negative ions were identified: Cl- abstraction, Cl2- abstraction, and electron detachment.
  • The decay processes exhibit a significant temperature dependence.
  • An experimental adiabatic electron affinity (Ea) of 1.6–1.9 eV was determined, significantly higher than theoretical values (0.9–1.0 eV).

Conclusions:

  • The study provides new insights into the gas-phase electron attachment and dissociation of hexachlorobenzene.
  • The observed temperature dependence of decay channels highlights complex dynamics.
  • A notable discrepancy between experimental and theoretical electron affinity values suggests the need for refined theoretical models.