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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 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).
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...
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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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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1,4-Bis(fluoro-meth-yl)benzene.

Hoong-Kun Fun, Reza Kia, P S Patil

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

    This study details the crystal structure of a difluoro compound, C(8)H(8)F(2), revealing short intermolecular C-F and F-F contacts. These interactions lead to the formation of 2D networks in the crystal lattice.

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    Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

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    Area of Science:

    • Solid-state chemistry
    • Crystallography
    • Supramolecular chemistry

    Background:

    • Understanding intermolecular interactions is crucial for predicting and controlling material properties.
    • Fluorinated organic compounds exhibit unique electronic and structural characteristics due to fluorine's high electronegativity.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, C(8)H(8)F(2).
    • To investigate the nature and significance of intermolecular contacts within the crystal lattice.
    • To characterize the self-assembly of molecules into higher-order structures.

    Main Methods:

    • Single-crystal X-ray diffraction analysis was employed to determine the three-dimensional molecular arrangement.
    • Analysis of interatomic distances and coordination numbers to identify significant intermolecular interactions.
    • Computational methods may be used to further analyze bonding and energetics (though not explicitly stated in the abstract).

    Main Results:

    • The C(8)H(8)F(2) molecule crystallizes with the molecule lying across a crystallographic inversion center.
    • Short C⋯F (2.8515 Å) and F⋯F (2.490 Å) contacts were observed, shorter than van der Waals radii sums.
    • Disordered fluorine and methylene hydrogen atoms were noted, with a site occupancy ratio of approximately 0.63:0.37.
    • Intermolecular C-H⋯F interactions form infinite chains along the b-axis.
    • C-H⋯π interactions further link molecules into a two-dimensional network parallel to the (101) plane.

    Conclusions:

    • The crystal structure is stabilized by a combination of short halogen contacts and hydrogen bonding interactions.
    • The observed C-H⋯F and C-H⋯π interactions dictate the formation of a 2D supramolecular network.
    • The findings contribute to the understanding of crystal engineering principles for fluorinated organic materials.