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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...
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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...
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

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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...
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Structure of Benzene: Kekulé Model

In 1865, August Kekule suggested the structure of benzene according to the structural theory of organic chemistry based on the three assertions—formula of benzene is C6H6, all the hydrogens of benzene are equivalent, and each carbon must have four bonds due to its tetravalency.
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.
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...

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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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1,3-Difluoro-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 investigates intermolecular forces in C(6)H(4)F(2), revealing how weak C-H⋯F and C-H⋯π interactions dictate crystal structure. These hydrogen bonds and π-interactions form complex 1D, 2D, and 3D arrangements.

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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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    Area of Science:

    • Crystal engineering
    • Supramolecular chemistry
    • Organic fluorine compounds

    Background:

    • The forces between C(δ+)-F(δ-) and H(δ+)-C(δ-) are near the hydrogen-bond limit.
    • These interactions are weak, poorly directional, and easily disrupted by stronger forces like C-H⋯π.

    Purpose of the Study:

    • To analyze the crystal structure of C(6)H(4)F(2).
    • To understand the role of weak interactions in directing the self-assembly of molecules.

    Main Methods:

    • X-ray crystallography to determine the molecular and crystal structure.
    • Analysis of intermolecular interactions, including hydrogen bonding (C-H⋯F) and π-interactions (C-H⋯π).

    Main Results:

    • C(6)H(4)F(2) (Z'=2) forms 1D tapes via homodromic C-H⋯F hydrogen bonds.
    • These tapes assemble into 2D corrugated sheets through bifurcated and trifurcated C-H⋯F bonds.
    • C-H⋯π interactions organize the packing in the third dimension.

    Conclusions:

    • Weak C-H⋯F and C-H⋯π interactions are crucial in dictating the supramolecular architecture of C(6)H(4)F(2).
    • The study demonstrates the hierarchical assembly from 1D tapes to 2D sheets and 3D packing driven by specific non-covalent interactions.