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

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

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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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...
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Related Experiment Video

Updated: Jun 5, 2026

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

4-Iodo-3,3'-dimethoxy-biphen-yl.

Qamar Ali, Zahid Hussain, Muhammad Raza Shah

    Acta Crystallographica. Section E, Structure Reports Online
    |January 5, 2011
    PubMed
    Summary
    This summary is machine-generated.

    This study on C(14)H(13)IO(2) reveals no π-π stacking. However, a short intermolecular iodine-oxygen distance suggests potential weak interactions in this crystal structure.

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

    Published on: July 30, 2017

    Area of Science:

    • Crystallography
    • Solid-state chemistry

    Background:

    • Understanding intermolecular interactions is crucial for predicting material properties.
    • The role of halogen bonding and other non-covalent interactions in organic molecules is an active area of research.

    Purpose of the Study:

    • To characterize the crystal structure of the title compound C(14)H(13)IO(2).
    • To investigate the presence and nature of intermolecular interactions, specifically π-π stacking and halogen bonding.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
    • Analysis of the crystal structure included measuring dihedral angles and identifying short intermolecular contacts.

    Main Results:

    • The crystal structure of C(14)H(13)IO(2) was determined.
    • No significant π-π interactions were observed between aromatic rings, with a dihedral angle of 43.72°.
    • A short intermolecular iodine-oxygen (I⋯O) distance of 3.408 Å was found, shorter than the sum of van der Waals radii.

    Conclusions:

    • The title compound does not exhibit π-π stacking in the solid state.
    • The short I⋯O contact indicates a potential weak intermolecular interaction, possibly a form of halogen bonding, influencing the crystal packing.