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Related Concept Videos

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...
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

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 eliminated to generate the benzyne...
Nomenclature of Aromatic Compounds with a Single Substituent01:23

Nomenclature of Aromatic Compounds with a Single Substituent

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).
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...
Nomenclature of Aromatic Compounds with Multiple Substituents01:11

Nomenclature of Aromatic Compounds with Multiple Substituents

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...
Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.

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Elucidating the Metabolism of 2,4-Dibromophenol in Plants
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Published on: February 10, 2023

3,6-Dibromo-phenanthrene.

Ruri Yokota1, Chitoshi Kitamura, Takeshi Kawase

  • 1Department of Materials Science and Chemistry, Graduate School of Engineering, University of Hyogo, 2167 Shosha, Himeji, Hyogo 671-2280, Japan.

Acta Crystallographica. Section E, Structure Reports Online
|January 4, 2013
PubMed
Summary

This study reveals the crystal structure of a dibrominated phenanthrene compound. Molecules arrange in a herringbone pattern with slipped pi-pi stacking, indicating specific intermolecular interactions in the solid state.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Materials Science

Background:

  • Phenanthrene derivatives are important in organic electronics and medicinal chemistry.
  • Understanding the solid-state structure of halogenated polycyclic aromatic hydrocarbons is crucial for predicting their properties.

Purpose of the Study:

  • To elucidate the crystal structure and intermolecular interactions of a specific dibrominated phenanthrene compound.
  • To analyze the planarity of the phenanthrene core and the positioning of bromine substituents.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of atomic deviations from planarity and intermolecular distances.

Main Results:

  • The phenanthrene ring is nearly planar, with minor deviations.
  • Bromine atoms show slight displacement from the phenanthrene plane.
  • Molecules form a herringbone arrangement with slipped face-to-face pi-pi stacking along the b-axis.
  • The crystal is a racemic twin with a minor twin fraction of 0.390(10).

Conclusions:

  • The study provides detailed structural information on dibrominated phenanthrene.
  • The observed crystal packing suggests specific intermolecular forces governing the solid-state organization.
  • The presence of a racemic twin highlights the importance of considering twinning in crystal structure analysis.