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Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

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...

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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.

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...

Reactions at the Benzylic Position: Halogenation

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.

Nucleophilic Aromatic Substitution: Elimination–Addition

Nucleophilic Aromatic Substitution: Elimination–Addition

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...

Diazonium Group Substitution: –OH and –H

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.

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Updated: Jun 1, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

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Published on: January 19, 2016

4-Chloro-benzothio-amide.

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 compound, C(7)H(6)ClNS. Key findings include specific dihedral angles, π-stacking interactions between aromatic rings, and intermolecular hydrogen bonding involving sulfur atoms.

Area of Science:

Crystallography
Chemical Physics
Organic Chemistry

Background:

Understanding the three-dimensional structure of organic molecules is crucial for predicting their properties and reactivity.
Thio-amide compounds are of interest due to their diverse applications in medicinal chemistry and materials science.

Purpose of the Study:

To elucidate the detailed crystal structure of the compound C(7)H(6)ClNS.
To investigate intermolecular interactions, including π-stacking and hydrogen bonding, within the crystal lattice.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
Analysis of the crystal structure involved measuring bond lengths, bond angles, and dihedral angles.

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Main Results:

The dihedral angle between the aromatic ring and the thio-amide group was determined to be 28.1(2)°.
Evidence of π-stacking interactions between offset aromatic rings was observed, with a centroid-centroid separation of 3.7942(2) Å.
Intermolecular hydrogen bonds were identified between the amino group and sulfur atoms.

Conclusions:

The crystal structure of C(7)H(6)ClNS reveals specific conformational preferences and significant intermolecular interactions.
These findings provide a structural basis for understanding the compound's physical and chemical behavior.
The identified hydrogen bonding and π-stacking interactions are key to the compound's solid-state assembly.