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Related Concept Videos

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.
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.
Preparation of Amines: Alkylation of Ammonia and Amines01:30

Preparation of Amines: Alkylation of Ammonia and Amines

Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
Structure of Amines01:19

Structure of Amines

The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
08:43

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

3-Methyl-anilinium nitrate.

Melanie Rademeyer1, David C Liles

  • 1Department of Chemistry, University of Pretoria, Pretoria 0002, South Africa.

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

This study reveals how 3-methyl-anilinium cations and nitrate anions form a stable two-dimensional network through strong hydrogen bonds. These interactions are key to understanding crystal structures and molecular assembly.

Area of Science:

  • Crystallography
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Understanding the non-covalent interactions in organic salts is crucial for designing new materials.
  • Anilinium nitrates are a class of compounds with potential applications in various fields.
  • The specific crystal structure and hydrogen bonding patterns dictate the bulk properties of these salts.

Purpose of the Study:

  • To elucidate the crystal structure of 3-methyl-anilinium nitrate.
  • To characterize the hydrogen bonding interactions between the 3-methyl-anilinium cation and the nitrate anion.
  • To understand the formation of the two-dimensional hydrogen-bonded network.

Main Methods:

  • Single-crystal X-ray diffraction was used to determine the molecular and crystal structure.

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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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Published on: August 22, 2018

  • Analysis of hydrogen bonding geometries, including N-H···O interactions.
  • Visualization and analysis of the resulting supramolecular network.

    • Main Results:

    • The crystal structure of 3-methyl-anilinium nitrate (C(7)H(10)N(+)·NO(3)(-)) was successfully determined.
    • Strong, bifurcated N(+)-H⋯(O,O) hydrogen bonds were identified between the anilinium cations and nitrate anions.
    • A robust two-dimensional hydrogen-bonded network was formed, extending through the crystal lattice.

    Conclusions:

    • The crystal packing is dominated by strong hydrogen bonding interactions between the organic cation and inorganic anion.
    • The observed hydrogen bonding pattern leads to the formation of a stable, extended two-dimensional network.
    • This structural motif provides insights into the self-assembly principles of organic-inorganic hybrid salts.