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Related Concept Videos

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.
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
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.
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...

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Related Experiment Video

Updated: Jun 1, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
11:45

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

4,7-Diaza-1-azoniacyclo-nonane bromide.

Thorsten Allscher1, Peter Klüfers, Christine Neumann

  • 1Ludwig-Maximilians-Universität, Department Chemie und Biochemie, Butenandtstrasse 5-13, 81377 München, Germany.

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

The study details the bromide salt of monoprotonated 1,4,7-triaza-cyclo-nonane (tacn). It reveals intramolecular hydrogen bonding and direct cation-anion contacts involving bromide ions.

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Area of Science:

  • Coordination Chemistry
  • Supramolecular Chemistry
  • Chemical Crystallography

Background:

  • 1,4,7-triaza-cyclo-nonane (tacn) is a macrocyclic triamine with a C3 symmetry.
  • Protonation of tacn disrupts its symmetry and influences its coordination properties.
  • Hydrogen bonding plays a crucial role in the self-assembly and structural organization of molecular compounds.

Purpose of the Study:

  • To characterize the structural and bonding features of the monoprotonated tacn bromide salt.
  • To investigate the role of intramolecular and intermolecular hydrogen bonds in the crystal structure.
  • To understand cation-anion interactions in this macrocyclic ammonium salt.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to determine the molecular structure.
  • Hydrogen bond analysis was performed to identify and quantify N-H···Br interactions.
  • Spectroscopic methods may have been used for characterization (though not explicitly stated in the abstract).

Main Results:

  • The compound was identified as the bromide salt of monoprotonated 1,4,7-triaza-cyclo-nonane (tacnH+Br-).
  • Protonation breaks the threefold symmetry of the tacn ligand.
  • The ammonium proton forms a bifurcated intramolecular hydrogen bond to two endodentate amine nitrogens.
  • Direct N-H···Br hydrogen bonds link tacnH+ cations and Br- anions, establishing cation-anion contacts.

Conclusions:

  • The crystal structure reveals specific hydrogen bonding patterns that stabilize the monoprotonated tacn cation.
  • Intramolecular hydrogen bonding influences the conformation of the protonated macrocycle.
  • The study highlights the importance of hydrogen bonding in organizing ionic macrocyclic compounds.