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Electrophilic Aromatic Substitution: Nitration of Benzene

Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.

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.

Nomenclature of Aromatic Compounds with a Single Substituent

Nomenclature of Aromatic Compounds with a Single Substituent

Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).

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...

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic S_N1

Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...

2° Amines to N-Nitrosamines: Reaction with NaNO2

2° Amines to N-Nitrosamines: Reaction with NaNO₂

Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.

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N-Benzoyl-N'-phenyl-urea.

Andrzej Okuniewski¹, Jaroslaw Chojnacki, Barbara Becker

¹Department of Inorganic Chemistry, Gdansk University of Technology, Narutowicza 11/12, 80-233 Gdańsk, Poland.

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This study reveals the molecular structure of C(14)H(12)N(2)O(2), highlighting intramolecular hydrogen bonds that dictate its conformation. Crystal analysis shows molecules forming dimers through intermolecular hydrogen bonds.

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Area of Science:

Crystallography
Molecular Chemistry
Supramolecular Chemistry

Background:

Understanding molecular conformation and intermolecular interactions is crucial in chemistry.
Hydrogen bonding plays a significant role in determining crystal structures and material properties.

Purpose of the Study:

To elucidate the molecular conformation of the title compound, C(14)H(12)N(2)O(2).
To investigate the intermolecular interactions and crystal packing of the compound.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular structure.
Analysis of hydrogen bonding patterns, including intramolecular and intermolecular interactions.

Main Results:

The molecular conformation is stabilized by a strong intramolecular N-H⋯O=C hydrogen bond.
In the crystal lattice, molecules form centrosymmetric dimers via intermolecular N-H⋯O=C hydrogen bonds.
No significant interactions were observed between these molecular dimers.

Conclusions:

The crystal structure of C(14)H(12)N(2)O(2) is characterized by specific intramolecular and intermolecular hydrogen bonding.
The observed hydrogen bonding network dictates the supramolecular assembly in the solid state.