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Related Concept Videos

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.
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 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.
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...
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

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...

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Related Experiment Video

Updated: Jun 1, 2026

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
09:04

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products

Published on: September 9, 2016

Guanidinium 3-nitro-benzoate.

Graham Smith, Urs D Wermuth

    Acta Crystallographica. Section E, Structure Reports Online
    |May 19, 2011
    PubMed
    Summary

    This study details the crystal structure of an anhydrous guanidinium salt, revealing extensive hydrogen bonding. The guanidinium cation forms cyclic networks with carboxylate groups, creating undulating sheets in the 3D structure.

    Area of Science:

    • Crystallography
    • Supramolecular Chemistry
    • Materials Science

    Background:

    • Guanidinium salts are important in various chemical and biological systems.
    • Understanding hydrogen bonding in crystalline solids is crucial for predicting material properties.
    • The specific salt CH(6)N(3) (+)·C(7)H(4)NO(4) (-) was synthesized and characterized.

    Purpose of the Study:

    • To elucidate the three-dimensional crystal structure of the anhydrous guanidinium salt.
    • To analyze the hydrogen bonding network within the crystal lattice.
    • To describe the supramolecular architecture formed by cation-anion interactions.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
    • Analysis of the hydrogen bonding interactions, including bond lengths and angles.

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    Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
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    Modification and Functionalization of the Guanidine Group by Tailor-made Precursors

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    A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s
    07:38

    A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s

    Published on: September 25, 2017

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    Last Updated: Jun 1, 2026

    A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
    09:04

    A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products

    Published on: September 9, 2016

    Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
    09:45

    Modification and Functionalization of the Guanidine Group by Tailor-made Precursors

    Published on: April 27, 2017

    A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s
    07:38

    A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s

    Published on: September 25, 2017

  • Topological analysis of the supramolecular network.

    • Main Results:

    • The anhydrous guanidinium salt, CH(6)N(3) (+)·C(7)H(4)NO(4) (-), was structurally characterized.
    • A detailed N-H⋯O hydrogen-bond network was observed.
    • The guanidinium cation participates in three cyclic R(2) (1)(6) hydrogen-bonding associations with carboxylate O-atom acceptors.
    • Peripheral R(1) (2)(4) cation-anion interactions contribute to the formation of inter-linked undulating sheets.

    Conclusions:

    • The crystal structure reveals a robust hydrogen-bonding framework in the guanidinium salt.
    • The observed network of hydrogen bonds dictates the formation of a layered supramolecular architecture.
    • This structural insight is valuable for the design of novel crystalline materials with specific properties.