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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...

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...

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.

Amines to Amides: Acylation of Amines

Amines to Amides: Acylation of Amines

Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...

Determining the pH of Salt Solutions

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...

Acidity of 1-Alkynes

Acidity of 1-Alkynes

The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.

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Related Experiment Video

Updated: Jun 2, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

2-Acetyl-anilinium chloride.

R Prasath, P Bhavana, Seik Weng Ng

Acta Crystallographica. Section E, Structure Reports Online

|April 28, 2011

Summary

The cation of the title salt exhibits a nearly planar conformation, stabilized by intramolecular hydrogen bonds. In the crystal, these molecules form dimeric aggregates through intermolecular hydrogen bonds and other interactions.

Area of Science:

Crystallography
Chemical Physics

Background:

Understanding molecular conformation and intermolecular interactions is crucial in crystal engineering.
Hydrogen bonding and van der Waals forces play significant roles in crystal lattice formation.

Purpose of the Study:

To elucidate the crystal structure and intermolecular interactions of the title salt.
To investigate the factors stabilizing the molecular conformation and crystal packing.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the crystal structure.
Analysis of bond lengths, bond angles, and non-covalent interactions was performed.

Main Results:

The cation, C(8)H(10)NO(+)·Cl(-), displays a nearly planar conformation with a C-C-C-C torsion angle of 4.6(2)°.

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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 Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

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

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Published on: August 22, 2018

An intramolecular N-H⋯O hydrogen bond stabilizes the cation's conformation.

Centrosymmetric dimeric aggregates are formed in the crystal via N-H⋯Cl hydrogen bonds.

Additional C-H⋯Cl, C-H⋯O, and C-O⋯π interactions contribute to the crystal packing.

Conclusions:

The crystal structure reveals a combination of strong and weak interactions governing the assembly of the title salt.
The interplay of intramolecular and intermolecular forces dictates the observed planar conformation and dimeric aggregation.