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Related Concept Videos

Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
Halogenation of Alkenes02:46

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
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.
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

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...
Alkyl Halides02:45

Alkyl Halides

Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...

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

Published on: July 30, 2017

2-Bromo-p-terphen-yl.

Suk-Hee Moon, Heesook Yoon, Youngjin Kang

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

    Structural analysis of C(18)H(13)Br reveals specific dihedral angles between its aromatic rings. Intermolecular bromine interactions and C-H⋯π bonds stabilize the crystal packing in this organic compound.

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    Published on: October 24, 2017

    Area of Science:

    • Organic Chemistry
    • Crystallography
    • Solid-State Chemistry

    Background:

    • Understanding the three-dimensional structure of organic molecules is crucial for predicting their properties and reactivity.
    • Crystal packing forces significantly influence the physical characteristics of solid organic compounds.

    Purpose of the Study:

    • To determine the precise molecular geometry of the title compound, C(18)H(13)Br.
    • To investigate the intermolecular interactions responsible for crystal lattice stabilization.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to analyze the crystal structure.
    • Dihedral angles between aromatic ring planes were calculated.
    • Intermolecular interactions, including halogen bonding, were identified and quantified.

    Main Results:

    • The dihedral angles between the central benzene ring and the outer phenyl and bromo-phenyl rings were determined to be 33.47(8)° and 66.35(8)°, respectively.
    • Weak C-H⋯π interactions were observed within the crystal lattice.
    • A significant intermolecular Br⋯Br interaction with a distance of 3.5503(15) Å was identified.

    Conclusions:

    • The non-planar conformation of C(18)H(13)Br is characterized by specific dihedral angles.
    • Intermolecular bromine-bromine contacts and C-H⋯π interactions play a key role in stabilizing the crystal structure.
    • These findings contribute to the understanding of structure-property relationships in halogenated aromatic compounds.