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Related Concept Videos

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.
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.
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...
Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
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.

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Related Experiment Video

Updated: May 25, 2026

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
11:01

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

Published on: November 23, 2016

2-(2-Nitro-anilino)benzoic acid.

Xiao-Lin Zhu1, Lu Shi, Peng Jiang

  • 1Department of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|January 20, 2012
PubMed
Summary
This summary is machine-generated.

This study details the crystal structure of a nitro-substituted aromatic compound. Key findings include the nitro group

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Molecular Structure

Background:

  • Understanding the precise arrangement of atoms in organic molecules is crucial for predicting their properties.
  • Nitro-substituted aromatic compounds are important in various chemical applications.

Purpose of the Study:

  • To elucidate the detailed three-dimensional molecular structure of the title compound, C(13)H(10)N(2)O(4).
  • To investigate the intermolecular interactions and crystal packing within the solid state.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the atomic coordinates and bond parameters.
  • Analysis of the crystal structure included assessing planarity, dihedral angles, and hydrogen bonding.

Main Results:

  • The nitro nitrogen atom exhibited a slight deviation from the benzene ring plane (0.031 Å).
  • Aromatic rings were found to be oriented at a dihedral angle of 50.6°.
  • An intramolecular N-H⋯O hydrogen bond and intermolecular O-H⋯O interactions forming inversion dimers were identified in the crystal lattice.

Conclusions:

  • The study provides precise structural data for C(13)H(10)N(2)O(4), highlighting specific geometric features.
  • The identified hydrogen bonding patterns and crystal packing offer insights into the solid-state behavior of this nitroaromatic compound.