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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.
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
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...

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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

2,5-Dimethyl-anilinium nitrate.

Wajda Smirani1, Mohamed Rzaigui

  • 1Laboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna Bizerte, Tunisia.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary

This study details the crystal structure of a salt, revealing specific molecular arrangements. The findings highlight how ions form layered structures through hydrogen bonding in the solid state.

Area of Science:

  • Crystallography
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Understanding the solid-state structures of organic salts is crucial for predicting their physical and chemical properties.
  • Layered structures in crystalline materials can influence properties such as conductivity and mechanical strength.

Purpose of the Study:

  • To elucidate the crystal structure of the title salt, C(8)H(12)N(+)·NO(3) (-).
  • To investigate the intermolecular interactions, specifically hydrogen bonding, that govern the self-assembly of this salt in the solid state.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the three-dimensional arrangement of atoms within the crystal lattice.
  • Analysis of hydrogen bonding networks (N-H⋯O) and symmetry elements (mirror planes, m symmetry) was performed.

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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates
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One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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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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One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates
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One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates

Published on: January 15, 2018

Main Results:

  • The crystal structure reveals that all non-hydrogen atoms of the cation lie on mirror planes.
  • The nitrate anion exhibits m symmetry and participates in N-H⋯O hydrogen bonds.
  • These interactions facilitate the formation of layered structures parallel to the ab plane, integrating both cations and anions.

Conclusions:

  • The specific arrangement of ions and hydrogen bonding in this salt leads to a distinct layered supramolecular architecture.
  • The findings provide insights into the structure-property relationships of organic nitrate salts.