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Electrophilic Aromatic Substitution: Nitration of Benzene01:20

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.
Electrophilic Aromatic Substitution: Sulfonation of Benzene01:22

Electrophilic Aromatic Substitution: Sulfonation of Benzene

Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.
Diazonium Group Substitution: –OH and –H01:19

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.
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview

Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by water loss...
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

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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Related Experiment Video

Updated: Jun 5, 2026

Microwave-assisted One-pot Synthesis of N-succinimidyl-4-[18F]fluorobenzoate ([18F]SFB)
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Microwave-assisted One-pot Synthesis of N-succinimidyl-4-[18F]fluorobenzoate ([18F]SFB)

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S-Benzyl-isothio-uronium nitrate.

P Hemalatha, V Veeravazhuthi

    Acta Crystallographica. Section E, Structure Reports Online
    |January 5, 2011
    PubMed
    Summary
    This summary is machine-generated.

    The crystal structure reveals that the title compound, C(8)H(11)N(2)S(+)·NO(3) (-), forms one-dimensional chains. These chains are created by intermolecular hydrogen bonds between cations and anions.

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    Area of Science:

    • Crystallography
    • Chemical Physics
    • Materials Science

    Background:

    • Understanding the supramolecular assembly of organic salts is crucial for designing new materials.
    • Hydrogen bonding plays a significant role in crystal engineering and the formation of extended structures.

    Purpose of the Study:

    • To determine the crystal structure of the title compound, C(8)H(11)N(2)S(+)·NO(3) (-).
    • To investigate the intermolecular interactions governing the crystal packing.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to elucidate the three-dimensional crystal structure.
    • Analysis of intermolecular interactions, specifically hydrogen bonds, was performed.

    Main Results:

    • The crystal structure of C(8)H(11)N(2)S(+)·NO(3) (-) was successfully determined.
    • Intermolecular N-H⋯O hydrogen bonds were identified as the primary driving force for crystal assembly.
    • These interactions lead to the formation of one-dimensional chains propagating along the [110] direction.

    Conclusions:

    • The crystal structure highlights the importance of hydrogen bonding in the self-assembly of organic salts.
    • The observed one-dimensional chain structure provides insights into potential applications in materials science.
    • Further studies could explore the properties and potential modifications of these chain structures.