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Related Concept Videos

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.
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...
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 Primary Amines01:17

Nomenclature of Primary Amines

Primary, secondary, and tertiary amines are compounds consisting of one, two, and three alkyl groups connected to the amino group (–NH2), respectively. As depicted in Figure 1, the common name of the primary amines is obtained by adding the suffix -amine to the alkyl substituent attached to the amino group as the corresponding alkylamine.
Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
Structure of Conjugated Dienes01:16

Structure of Conjugated Dienes

Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...

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Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
07:06

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

Published on: November 15, 2017

Hexane-1,6-diammonium dinitrate.

Charmaine van Blerk1, Gert J Kruger

  • 1University of Johannesburg, Department of Chemistry, P O Box 524, Auckland Park, Johannesburg 2006, South Africa.

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

The crystal structure of hexane-1,6-diammonium nitrate reveals a non-planar hydrocarbon chain and a complex 3D hydrogen-bonding network. This network involves bifurcated interactions between ammonium and nitrate ions, forming intricate ring and chain motifs.

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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 structural properties of organic ammonium salts is crucial for designing new materials.
  • Hydrogen bonding plays a significant role in the self-assembly and properties of crystalline compounds.
  • Hexane-1,6-diammonium dinitrate is a relevant model compound for studying these interactions.

Purpose of the Study:

  • To elucidate the crystal structure of hexane-1,6-diammonium dinitrate.
  • To analyze the hydrogen bonding network and its influence on the molecular conformation.
  • To characterize the supramolecular architecture formed by the cation and anion.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the atomic arrangement.
  • Analysis of torsion angles was performed to assess the planarity of the hydrocarbon chain.
  • Hydrogen bond analysis, including graph set notation, was used to describe the network.

Main Results:

  • The hexane-1,6-diammonium cation was found to lie across a crystallographic inversion center.
  • Significant deviation from planarity was observed in the hydrocarbon chain, with specific torsion angles reported.
  • A three-dimensional hydrogen-bonding network was identified, featuring bifurcated interactions between ammonium and nitrate groups.
  • Complex ring and chain motifs, including a 26-membered ring (R(4)(4)(26)), were observed.

Conclusions:

  • The crystal structure of hexane-1,6-diammonium dinitrate exhibits a non-planar cation conformation due to steric and electronic factors.
  • The extensive hydrogen bonding network dictates the supramolecular assembly, leading to the formation of intricate motifs.
  • These findings contribute to the understanding of structure-property relationships in organic salts and hydrogen-bonded systems.