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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...
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.
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...
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.
Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles01:11

Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles

Naming Amides
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.

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Related Experiment Video

Updated: Jun 2, 2026

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

9-Amino-acridinium nitrate monohydrate.

Mehrdad Pourayoubi, Hossein Eshtiagh-Hosseini, Somayyeh Sanaei Ataabadi

    Acta Crystallographica. Section E, Structure Reports Online
    |April 28, 2011
    PubMed
    Summary

    This study details the crystal structure of a hydrated pyridine salt, C(13)H(11)N(2) (+)·NO(3) (-)·H(2)O. The analysis reveals extensive hydrogen bonding interactions forming a layered network.

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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

    Published on: August 22, 2018

    Area of Science:

    • Crystallography
    • Supramolecular Chemistry
    • Materials Science

    Background:

    • Understanding the hydrogen bonding patterns in organic salts is crucial for designing new materials.
    • Pyridine derivatives are common scaffolds in medicinal chemistry and materials science.
    • Hydrated salts offer unique structural possibilities due to water molecule interactions.

    Purpose of the Study:

    • To elucidate the crystal structure of the title hydrated salt, C(13)H(11)N(2) (+)·NO(3) (-)·H(2)O.
    • To characterize the hydrogen bonding network involving the pyridine cation, nitrate anions, and water molecule.
    • To investigate the resulting supramolecular architecture in the solid state.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
    • Analysis of hydrogen bonding interactions was performed using crystallographic data.
    • The conformation of the pyridine N atom and the amino group was examined.

    Main Results:

    • The pyridine N atom of the cation is protonated and hydrogen-bonded to a water molecule.
    • The amino group exhibits a planar conformation and participates in three N-H⋯O hydrogen bonds with nitrate anions.
    • The water molecule forms hydrogen bonds with two adjacent nitrate anions, leading to a layered network structure.

    Conclusions:

    • The crystal structure is stabilized by a complex hydrogen bonding network.
    • The observed layered network is a direct consequence of the specific interactions between the cation, anion, and water.
    • This detailed structural analysis provides insights into the self-assembly of hydrated organic salts.