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Related Concept Videos

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.
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: 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.
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...
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...

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Related Experiment Video

Updated: May 26, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
19:58

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

1-Bromo-2-[(E)-2-nitro-ethen-yl]benzene.

Pei-Hua Zhao, Zhan-Heng Feng, Mei Zhang

    Acta Crystallographica. Section E, Structure Reports Online
    |December 27, 2011
    PubMed
    Summary

    The crystal structure of C(8)H(6)BrNO(2) reveals a 22.99° dihedral angle between the benzene ring and nitro group. Short bromine-oxygen contacts form inversion dimers in the crystal lattice.

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Solid-State Chemistry

    Background:

    • Understanding molecular interactions and crystal packing is crucial in solid-state chemistry.
    • The study of halogenated nitroaromatic compounds provides insights into intermolecular forces.

    Purpose of the Study:

    • To determine the crystal structure of the title compound, C(8)H(6)BrNO(2).
    • To analyze the molecular conformation, specifically the dihedral angle between the benzene ring and the nitro group.
    • To investigate intermolecular interactions, such as halogen bonding, within the crystal lattice.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to elucidate the three-dimensional structure of the compound.
    • Crystallographic data were analyzed to determine bond lengths, bond angles, and intermolecular contacts.

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    Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
    09:54

    Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

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    Last Updated: May 26, 2026

    Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
    19:58

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    Published on: July 30, 2017

    Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties
    10:16

    Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties

    Published on: January 8, 2016

    Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
    09:54

    Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

    Published on: September 12, 2018

    Main Results:

    • The dihedral angle between the benzene ring and the nitro group was found to be 22.99(12)°.
    • Inversion dimers were observed in the crystal structure, stabilized by short bromine-oxygen (Br⋯O) contacts measuring 3.2319(17) Å.

    Conclusions:

    • The crystal structure of C(8)H(6)BrNO(2) is characterized by a specific non-planar conformation.
    • The observed Br⋯O contacts indicate the presence of halogen bonding, influencing crystal packing and stability.