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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

1.9K
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...
1.9K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

3.3K
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.
3.3K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

1.9K
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.
1.9K
Preparation of Nitriles01:12

Preparation of Nitriles

1.9K
One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
1.9K
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

3.9K
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.
3.9K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

2.0K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
2.0K

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Related Experiment Video

Updated: May 4, 2026

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
06:44

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

71.2K

2,3-Xylidinium nitrate.

Chourouk Kefi1, Houda Marouani1, Mohamed Rzaigui1

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

Acta Crystallographica. Section E, Structure Reports Online
|January 16, 2014
PubMed
Summary

The crystal structure of 2,3-xylidinium nitrate reveals layered networks formed by hydrogen bonds between the organic cations and nitrate anions. These interactions create a complex three-dimensional framework.

Area of Science:

  • Crystallography
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Understanding the intermolecular interactions in organic salts is crucial for designing new materials.
  • Crystal engineering relies on predicting and controlling the assembly of molecules in the solid state.

Purpose of the Study:

  • To elucidate the crystal structure of 2,3-xylidinium nitrate.
  • To investigate the hydrogen bonding network governing the assembly of the crystal structure.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the crystal structure.
  • Analysis of hydrogen bond donors and acceptors was performed to identify intermolecular interactions.

Main Results:

  • The crystal structure features 2,3-xylidinium cations and nitrate anions.

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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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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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  • Bifurcated N-H⋯(O,O) and weak C-H⋯O hydrogen bonds connect the cations and anions.
  • Corrugated layers parallel to (001) are formed, further linked by C-H⋯O interactions into a 3D network.

    • Conclusions:

    • The hydrogen bonding network dictates the formation of a robust three-dimensional framework in 2,3-xylidinium nitrate.
    • The study provides insights into the supramolecular assembly of organic nitrates.