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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.
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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

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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...
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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 constants depend...

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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

2-Fluoro-N-o-tolyl-benzamide.

Aamer Saeed, Rasheed Ahmad Khera, Shahid Ameen

    Acta Crystallographica. Section E, Structure Reports Online
    |May 18, 2011
    PubMed
    Summary

    This study investigates the crystal structure of a fluorinated organic compound, C(14)H(12)FNO. It details molecular geometry, including disordered fluorine atoms and dihedral angles, and describes intermolecular interactions stabilizing the crystal lattice.

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    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Materials Science

    Background:

    • Understanding the precise three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and designing new materials.
    • Fluorinated organic compounds exhibit unique electronic and physical characteristics, making them valuable in various applications.

    Purpose of the Study:

    • To elucidate the detailed crystal structure of the title compound, C(14)H(12)FNO.
    • To analyze the molecular geometry, including atomic disorder and planarity of functional groups.
    • To investigate the intermolecular interactions that govern the crystal packing and stability.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the atomic arrangement.
    • Crystallographic data analysis was performed to obtain bond lengths, bond angles, and dihedral angles.
    • Analysis of intermolecular interactions, including hydrogen bonding and pi-pi stacking, was conducted.

    Main Results:

    • The ortho-fluorine atom on the fluoro-benzene ring exhibits positional disorder.
    • The amide unit is planar, with specific dihedral angles observed between the amide plane and the two aromatic rings.
    • The crystal structure is stabilized by a network of N-H⋯O, C-H⋯π, C-H⋯O, and C-H⋯F interactions, forming chains and layers.

    Conclusions:

    • The study provides a comprehensive structural characterization of C(14)H(12)FNO.
    • The observed disorder and specific molecular conformations offer insights into the compound's solid-state behavior.
    • The identified intermolecular interactions highlight key factors for crystal stabilization and potential for further material design.