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Related Concept Videos

Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.
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.
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...
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.
Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.

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Related Experiment Video

Updated: May 19, 2026

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

1,3-Dinitro-soimidazolidine.

Augusto Rivera, Diego Quiroga, Jaime Ríos-Motta

    Acta Crystallographica. Section E, Structure Reports Online
    |August 21, 2012
    PubMed
    Summary
    This summary is machine-generated.

    This study reveals the crystal structure of a nitrogen-rich compound, C(3)H(6)N(4)O(2), detailing its partial disorder and unique molecular conformations. The findings highlight specific nitroso group arrangements and imidazolidine ring strain within the crystal lattice.

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    Facile Preparation of 4-Substituted Quinazoline Derivatives
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    Facile Preparation of 4-Substituted Quinazoline Derivatives

    Published on: February 15, 2016

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    Facile Preparation of 4-Substituted Quinazoline Derivatives
    11:51

    Facile Preparation of 4-Substituted Quinazoline Derivatives

    Published on: February 15, 2016

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Materials Science

    Background:

    • Understanding the crystal structure of novel organic compounds is crucial for predicting their properties and potential applications.
    • Nitrogen-rich compounds often exhibit unique electronic and structural characteristics due to the high nitrogen content.

    Purpose of the Study:

    • To elucidate the detailed crystal structure of the title compound, C(3)H(6)N(4)O(2).
    • To investigate the conformational aspects and disorder within the crystal lattice of this nitrogen-rich molecule.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular structure and arrangement in the solid state.
    • Refinement of crystallographic data was performed to analyze the partial disorder and precise atomic positions.

    Main Results:

    • The compound C(3)H(6)N(4)O(2) exhibits significant partial disorder, with two distinct components refined at occupancy ratios of 0.582(5):0.418(5).
    • The nitroso groups display syn and anti spatial arrangements in the major and minor components, respectively, with near-coplanar N-N=O moieties.
    • The imidazolidine ring adopts a twisted conformation in both components, indicating ring strain evidenced by specific torsion angles.

    Conclusions:

    • The crystal structure of C(3)H(6)N(4)O(2) is characterized by partial positional disorder and distinct conformational preferences of the nitroso and imidazolidine groups.
    • Weak C-H⋯O hydrogen bonds play a role in stabilizing the crystal packing.
    • The findings provide fundamental structural insights into this nitrogen-rich organic compound.