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Hydrolysis of Chlorobenzene to Phenol: Dow Process

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Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...

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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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Diazonium Group Substitution: –OH and –H

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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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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...

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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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N'-(2-Chloro-benzyl-idene)benzo-hydrazide.

Chuan-Gang Fan¹, Ming-Zhi Song

¹College of Chemistry and Chemical Technology, Binzhou University, Binzhou 256600, Shandong, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This study details the crystal structure of a novel compound, C(14)H(11)ClN(2)O. Analysis reveals two distinct molecular arrangements and intermolecular hydrogen bonds influencing crystal packing.

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Area of Science:

Crystallography
Organic Chemistry
Solid-State Chemistry

Background:

The study investigates the solid-state structure of a specific organic compound.
Understanding molecular arrangements in crystals is crucial for predicting material properties.

Purpose of the Study:

To elucidate the crystal structure of the title compound, C(14)H(11)ClN(2)O.
To analyze the molecular conformation and intermolecular interactions within the crystal lattice.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the crystal structure.
The asymmetric unit was analyzed to identify independent molecules and their conformations.

Main Results:

The asymmetric unit contains two independent molecules of C(14)H(11)ClN(2)O.
Dihedral angles between aromatic rings differ significantly between the two independent molecules (45.94° and 58.48°).
Intermolecular N-H⋯O hydrogen bonds form two independent sets of chains along the [001] direction.

Conclusions:

The crystal structure is characterized by the presence of two distinct molecular conformers.
Hydrogen bonding plays a significant role in organizing the molecules into extended chain structures.