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Related Concept Videos

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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...
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.
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).
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).

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Related Experiment Video

Updated: Jun 1, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
08:43

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

1,2,3-Trifluoro-benzene.

Michael T Kirchner, Dieter Bläser, Roland Boese

    Acta Crystallographica. Section E, Structure Reports Online
    |May 18, 2011
    PubMed
    Summary
    This summary is machine-generated.

    This study examines trifluorobenzene crystal structure, revealing that weak C-H⋯F interactions and π-π stacking form intricate 1D, 2D, and 3D networks. These forces dictate molecular arrangement and crystal packing.

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    Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
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    Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

    Published on: July 28, 2018

    1,3,5-Triphenylbenzene and Corannulene as Electron Receptors for Lithium Solvated Electron Solutions
    06:56

    1,3,5-Triphenylbenzene and Corannulene as Electron Receptors for Lithium Solvated Electron Solutions

    Published on: October 10, 2016

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    Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
    08:43

    Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

    Published on: January 19, 2016

    Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
    10:10

    Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

    Published on: July 28, 2018

    1,3,5-Triphenylbenzene and Corannulene as Electron Receptors for Lithium Solvated Electron Solutions
    06:56

    1,3,5-Triphenylbenzene and Corannulene as Electron Receptors for Lithium Solvated Electron Solutions

    Published on: October 10, 2016

    Area of Science:

    • Crystal Engineering
    • Supramolecular Chemistry
    • Organic Solid-State Chemistry

    Background:

    • Understanding intermolecular forces is crucial for predicting and controlling crystal structures.
    • Fluorinated organic compounds exhibit unique electronic properties and intermolecular interactions.
    • π-π stacking and hydrogen bonding are key non-covalent interactions in crystal packing.

    Purpose of the Study:

    • To elucidate the crystal structure of 1,3,5-trifluorobenzene.
    • To investigate the role of weak C-H⋯F hydrogen bonds and π-π stacking in its crystal packing.
    • To characterize the dimensionality of the resulting network structures.

    Main Methods:

    • Single-crystal X-ray diffraction analysis was employed.
    • Analysis of intermolecular contacts, including C-H⋯F bonds and π-π stacking, was performed.
    • Crystal structure visualization and network analysis were conducted.

    Main Results:

    • The molecule crystallizes with a twofold rotation axis.
    • One-dimensional tapes are formed by anti-dromic C-H⋯F hydrogen bonds.
    • These tapes assemble into corrugated 2D sheets via bifurcated C-H⋯F bonds.
    • π-π stacking interactions with a centroid-centroid distance of 3.6362(14) Å connect sheets into a 3D packing.

    Conclusions:

    • Weak C-H⋯F interactions, though borderline, are directional and significant in forming the crystal architecture.
    • π-π stacking plays a crucial role in the third dimension of crystal packing.
    • The study highlights the interplay of different non-covalent forces in constructing complex supramolecular assemblies.