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Related Concept Videos

Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

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Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is...
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NMR Spectroscopy of Benzene Derivatives01:34

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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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Nomenclature of Aromatic Compounds with Multiple Substituents01:11

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When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
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Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
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Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

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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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Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

2.5K
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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Updated: Dec 29, 2025

Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties
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3,5-Dichloro-3',4'-dimethoxybiphenyl.

Ram Dhakal1, Sean Parkin2, Hans-Joachim Lehmler1

  • 1The University of Iowa, Department of Occupational and Environmental Health, University of Iowa Research Park, Iowa City, IA 52242, USA.

Iucrdata
|February 8, 2020
PubMed
Summary
This summary is machine-generated.

This study characterizes 3,5-Dichloro-3

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Area of Science:

  • Organic Chemistry
  • Crystallography
  • Environmental Science

Background:

  • Polychlorinated biphenyls (PCBs) are persistent organic pollutants.
  • Metabolites of PCBs can exhibit unique chemical properties and biological activities.
  • Understanding PCB metabolites is crucial for environmental and health risk assessment.

Purpose of the Study:

  • To elucidate the crystal structure and intermolecular interactions of 3,5-Dichloro-3',4'-dimethoxybiphenyl.
  • To investigate the structural characteristics of a dihydroxylated metabolite of 3,4-dichlorobiphenyl (PCB 14).

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of π-π stacking interactions and dihedral angles between aromatic rings.
  • Determination of the orientation of methoxy substituents relative to the biphenyl core.

Main Results:

  • The crystal structure revealed π-π stacking interactions between inversion-related chlorinated benzene rings.
  • An inter-planar stacking distance of 3.3695 (17) Å was measured.
  • The dihedral angle between the benzene rings was 42.49 (6)°, indicating a non-planar conformation.
  • Methoxy groups were found to lie nearly in the plane of their respective benzene rings.

Conclusions:

  • The structural data provides insight into the solid-state behavior of this specific PCB metabolite.
  • The observed π-π stacking and dihedral angles influence the molecule's packing and potential interactions in condensed phases.
  • This detailed structural characterization contributes to the broader understanding of chlorinated biphenyl metabolism and environmental fate.