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Related Concept Videos

Carbocations02:10

Carbocations

Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...
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...
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...
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.

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Updated: Jun 1, 2026

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core
08:51

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2,7-Dibromo-9-octyl-9H-carbazole.

Eric Gagnon, Dominic Laliberté

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

    This study reveals how octyl chains in a C(20)H(23)Br(2)N crystal structure form bilayers, isolating carbazole units. These units exhibit offset π-π interactions and C-H⋯π interactions, with bromine atoms showing a short contact.

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Materials Science

    Background:

    • Carbazole derivatives are important in organic electronics.
    • Understanding crystal packing influences material properties.

    Purpose of the Study:

    • To elucidate the crystal structure of C(20)H(23)Br(2)N.
    • To investigate intermolecular interactions within the crystal lattice.

    Main Methods:

    • Single-crystal X-ray diffraction analysis.
    • Analysis of molecular conformation and intermolecular contacts.

    Main Results:

    • The crystal structure features extended anti-conformation octyl chains forming segregating bilayers.
    • Carbazole units are isolated and participate in offset π-π interactions (4.2822 Å centroid-to-centroid).

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    Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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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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    Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
    10:44

    Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

    Published on: April 19, 2019

  • Short C-H⋯π interactions (2.96, 2.99 Å) and a short Br⋯Br contact (3.5475 Å) were observed.

    • Conclusions:

    • The crystal packing is dictated by the interplay of alkyl chain segregation and carbazole π-stacking.
    • Observed intermolecular interactions, including a short Br-Br contact, suggest potential for unique solid-state properties.