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Nomenclature of Aryl and Heterocyclic Amines

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.

Radical Substitution: Allylic Bromination

Radical Substitution: Allylic Bromination

In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...

2° Amines to N-Nitrosamines: Reaction with NaNO2

2° Amines to N-Nitrosamines: Reaction with NaNO₂

Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.

Electrophilic Aromatic Substitution: Nitration of Benzene

Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric 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.

Physical Properties of Amines

Physical Properties of Amines

Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.

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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

N,N-Bis(2-bromo-ethyl)aniline.

R Vilma Bojan¹, Richard A Varga, Cristian Silvestru

¹Facultatea de Chimie si Inginerie Chimica, Univesitatea Babes-Bolyai, Cluj-Napoca, Ro-40028, Romania.

Acta Crystallographica. Section E, Structure Reports Online

|January 5, 2011

Summary

This summary is machine-generated.

This study details the molecular structure of a novel dibrominated nitrogen-containing compound. Intermolecular interactions create a unique three-dimensional crystal structure.

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Area of Science:

Crystallography
Organic Chemistry
Supramolecular Chemistry

Background:

Understanding the structural properties of halogenated organic compounds is crucial for predicting their reactivity and applications.
Nitrogen-containing organic molecules with specific geometries are foundational in medicinal chemistry and materials science.

Purpose of the Study:

To elucidate the crystal structure of the title compound, C(10)H(13)Br(2)N.
To investigate the molecular geometry and intermolecular interactions within the crystal lattice.

Main Methods:

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

Main Results:

The molecule possesses a twofold rotation axis coincident with the N-C(phenyl) bond.
A slightly distorted trigonal planar geometry was observed around the nitrogen atom.
Intermolecular C-H⋯Br interactions were identified, leading to a 3D supramolecular architecture.

Conclusions:

The study provides a detailed structural characterization of the title compound.
The observed intermolecular interactions dictate the formation of an extended three-dimensional network.
This structural insight is valuable for designing related compounds with tailored properties.