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Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

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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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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 Bromination

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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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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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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...

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4-Bromo-thio-benzamide.

Mahmood-Ul-Hassan Khan, Shahid Hameed, Tashfeen Akhtar

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This study details the crystal structure of a novel brominated aromatic thioamide, C(7)H(6)BrNS. The research reveals specific molecular arrangements and intermolecular hydrogen bonding critical for its solid-state properties.

Area of Science:

Crystallography
Organic Chemistry
Solid-State Chemistry

Background:

Understanding the solid-state structure of organic compounds is crucial for predicting their physical and chemical properties.
Thioamide derivatives are important in medicinal chemistry and materials science.
The specific compound C(7)H(6)BrNS has not been previously characterized in detail.

Purpose of the Study:

To elucidate the crystal structure of C(7)H(6)BrNS.
To analyze the molecular conformation and intermolecular interactions within the crystal lattice.
To provide a foundation for further studies on the properties and applications of this compound.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the crystal structure.

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The crystallographic data were analyzed to obtain bond lengths, bond angles, and dihedral angles.

Intermolecular interactions, specifically hydrogen bonding, were identified and characterized.

Main Results:

The compound C(7)H(6)BrNS crystallizes with two molecules in the asymmetric unit.
Dihedral angles between the aromatic ring and the thioamide fragment were measured as 23.6(4)° and 20.5(3)°.
Intermolecular N-H⋯S hydrogen bonds were observed, linking molecules in the crystal structure.

Conclusions:

The crystal structure of C(7)H(6)BrNS has been successfully determined.
The observed dihedral angles indicate a specific torsional arrangement between the aromatic and thioamide moieties.
The presence of N-H⋯S hydrogen bonds plays a significant role in stabilizing the crystal packing.