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Preparation of Acid Anhydrides

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...

Acid Halides to Amides: Aminolysis

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...

Alkyl Halides

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...

Electrophilic Addition to Alkynes: Halogenation

Electrophilic Addition to Alkynes: Halogenation

Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.

Reactions of Acid Anhydrides

Reactions of Acid Anhydrides

The reactions of acid anhydrides are analogous to the reactions of acid chlorides and proceed via a nucleophilic acyl substitution. They only differ in the identity of the leaving group. During an acid chloride reaction, the leaving group is a chloride ion, and the by-product is hydrochloric acid. However, in an acid anhydride reaction, the leaving group is a carboxylate ion, and the by-product is a carboxylic acid.

Diazonium Group Substitution: –OH and –H

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.

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Related Experiment Video

Updated: Jun 5, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

3-Cyano-anilinium chloride.

Xiao-Chun Wen¹

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

|January 5, 2011

Summary

This study reveals that in the title salt, the organic cations and chloride ions form a 2D network structure through hydrogen bonding. This crystal structure analysis provides insights into supramolecular chemistry.

Area of Science:

Crystallography
Supramolecular Chemistry
Materials Science

Background:

Understanding the crystal structure of organic salts is crucial for predicting their physical and chemical properties.
Hydrogen bonding plays a significant role in the self-assembly of molecular structures.
The title salt, C(7)H(7)N(2) (+)·Cl(-), represents a model system for studying such interactions.

Purpose of the Study:

To determine the precise crystal structure of the title salt, C(7)H(7)N(2) (+)·Cl(-).
To investigate the nature of intermolecular interactions, specifically hydrogen bonding, within the crystal lattice.
To elucidate the formation of extended network structures in the solid state.

Main Methods:

Single-crystal X-ray diffraction was employed to analyze the crystal structure.

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

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The atomic coordinates and bond lengths/angles were refined.

Analysis of intermolecular contacts, including hydrogen bonds, was performed.

Main Results:

The crystal structure consists of organic cations (C(7)H(7)N(2) (+)) and chloride anions (Cl(-)).
All non-hydrogen atoms of the cation exhibit near-planarity, with a root-mean-square deviation of 0.005 Å.
A two-dimensional network structure is formed parallel to the (001) plane, driven by N-H⋯Cl hydrogen bonds between cations and anions.

Conclusions:

The title salt exhibits a well-defined crystal structure characterized by planar organic cations.
N-H⋯Cl hydrogen bonds are the primary driving force for the formation of a 2D supramolecular network.
The findings contribute to the understanding of crystal engineering and the design of materials with specific network architectures.