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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...

Structures of Carboxylic Acid Derivatives

Structures of Carboxylic Acid Derivatives

Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...

Preparation of Amines: Alkylation of Ammonia and Amines

Preparation of Amines: Alkylation of Ammonia and Amines

Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...

Amides to Carboxylic Acids: Hydrolysis

Amides to Carboxylic Acids: Hydrolysis

Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires severe conditions.
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...

Structure of Amines

Structure of Amines

The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...

Amines to Sulfonamides: The Hinsberg Test

Amines to Sulfonamides: The Hinsberg Test

The Hinsberg test is a method to identify primary, secondary and tertiary amines, named after its pioneer, Oscar Hinsberg. Here, amines are treated with benzenesulfonyl chloride, also known as the Hinsberg reagent, in the presence of an excess of aqueous base, followed by acidification. Based on the nature of the amines, different changes are observed.
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing sulfonyl...

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Related Experiment Video

Updated: Jun 5, 2026

Hydrophobic Salt-modified Nafion for Enzyme Immobilization and Stabilization

Hydrophobic Salt-modified Nafion for Enzyme Immobilization and Stabilization

Published on: July 11, 2012

N-Hydroxy-N-methyl-ammonium chloride.

¹Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia.

Acta Crystallographica. Section E, Structure Reports Online

|January 5, 2011

Summary

The crystal structure of CH(6)NO(+)·Cl(-) reveals cations and anions forming an undulating layer via hydrogen bonds. This arrangement results in all non-hydrogen atoms lying on a single mirror plane.

Area of Science:

Crystallography
Solid-state chemistry

Background:

Understanding the supramolecular assembly of ionic compounds is crucial for materials science.
Hydrogen bonding plays a significant role in dictating crystal packing and network formation.

Purpose of the Study:

To elucidate the crystal structure of the title compound, CH(6)NO(+)·Cl(-).
To characterize the hydrogen bonding interactions and resulting supramolecular architecture.

Main Methods:

Single-crystal X-ray diffraction analysis was employed to determine the three-dimensional crystal structure.
Analysis of intermolecular interactions, specifically hydrogen bonds, was performed.

Main Results:

The crystal structure consists of CH(6)NO(+) cations and Cl(-) anions.

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N-H⋯Cl and O-H⋯Cl hydrogen bonds link the ions into an undulating layer motif with Schläfli symbol 4(8).6(8).8(2).

All non-hydrogen atoms were found to lie on a crystallographic mirror plane.

Conclusions:

The hydrogen bonding network dictates the formation of a specific layered structure in CH(6)NO(+)·Cl(-).
The observed structural features provide insights into the solid-state behavior of this ionic compound.