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Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
Determining the pH of Salt Solutions04:08

Determining the pH of Salt Solutions

The pH of a salt solution is determined by its component anions and cations. Salts that contain pH-neutral anions and the hydronium ion-producing cations form a solution with a pH less than 7. For example, in ammonium nitrate (NH4NO3) solution, NO3− ions do not react with water whereas NH4+ ions produce the hydronium ions resulting in the acidic solution. In contrast, salts that contain pH-neutral cations and the hydroxide ion-producing anions form a solution with a pH greater than 7. For...
Preparation of Acid Anhydrides01:07

Preparation of Acid Anhydrides

One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
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.
Alkyl Halides02:45

Alkyl Halides

Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
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...

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Related Experiment Video

Updated: Jun 1, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
08:43

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

2,4-Dimethyl-anilinium chloride.

Ji-Yuan Yao1

  • 1Ordered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|May 19, 2011
PubMed
Summary

The crystal structure of C(8)H(12)N(+)·Cl(-) reveals ammonium hydrogen atoms forming hydrogen bonds with chloride ions. These interactions create 16-membered macrocyclic rings from four formula units.

Area of Science:

  • Crystallography
  • Supramolecular Chemistry
  • Chemical Physics

Background:

  • Understanding the hydrogen bonding patterns in organic salts is crucial for predicting their solid-state structures and properties.
  • The formation of ordered supramolecular assemblies influences material characteristics.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C(8)H(12)N(+)·Cl(-).
  • To investigate the hydrogen bonding interactions and resulting supramolecular architecture.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to determine the three-dimensional arrangement of atoms.
  • Analysis of intermolecular distances and angles to identify hydrogen bonding networks.

Main Results:

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  • The crystal structure confirmed the presence of ammonium cations and chloride anions.
  • All hydrogen atoms on the ammonium nitrogen were involved in hydrogen bonding with chloride ions.
  • Observed N⋯Cl distances ranged from 3.080(2) to 3.136(2) Å.
  • A distinctive 16-membered macrocyclic ring was formed, involving four formula units of the compound.

Conclusions:

  • The hydrogen bonding network dictates the formation of a specific supramolecular architecture in the solid state.
  • The identified macrocyclic structures are a direct consequence of the directional hydrogen bonding between ammonium and chloride ions.