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Related Concept Videos

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.
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.
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...
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.
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...

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Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
09:58

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Bis(2-bromo-benz-yl) tris-ulfide.

Suneel P Singh, Alan J Lough, Adrian L Schwan

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

    This study details the crystal structure of a novel molecule, C(14)H(12)Br(2)S(3). Key findings include its unique symmetry and bond angles, offering insights into molecular geometry and chemical bonding principles.

    Area of Science:

    • Crystallography
    • Molecular Chemistry
    • Chemical Bonding

    Background:

    • Understanding the precise three-dimensional arrangement of atoms in molecules is crucial for predicting chemical behavior.
    • The study of novel sulfur-containing organic compounds can reveal unique structural motifs and bonding characteristics.

    Purpose of the Study:

    • To elucidate the crystal structure of the title molecule, C(14)H(12)Br(2)S(3).
    • To analyze the molecular geometry, including symmetry elements and bond angles.
    • To compare observed bond angles with theoretical predictions based on hybridization principles.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular structure.
    • Crystallographic data analysis was performed to identify symmetry elements and measure bond distances and angles.

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  • Geometric parameters were analyzed in the context of hybridization theory.

    • Main Results:

    • The molecule C(14)H(12)Br(2)S(3) crystallizes with a twofold rotation axis bisecting the S-S-S angle.
    • A near-orthogonal dihedral angle of 89.91° was observed between the two benzene rings.
    • The S-C-C bond angle was found to be slightly larger than predicted by standard hybridization models.

    Conclusions:

    • The crystal structure of C(14)H(12)Br(2)S(3) exhibits unique symmetry and geometric features.
    • The observed deviations in bond angles provide valuable experimental data for refining theoretical models of chemical bonding.
    • This research contributes to the understanding of structural diversity in organosulfur compounds.