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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.

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.

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.

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.

NMR Spectroscopy of Benzene Derivatives

NMR Spectroscopy of Benzene Derivatives

Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling constants depend...

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...

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Updated: May 31, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

4-Bromo-N-phenyl-aniline.

Emily J Hefter¹, Joseph M Tanski

¹Department of Chemistry, Vassar College, Poughkeepsie, NY 12604, USA.

Acta Crystallographica. Section E, Structure Reports Online

|July 15, 2011

Summary

This study details the molecular structure of C(12)H(10)BrN, revealing specific dihedral and pitch angles between its benzene rings. The compound features intermolecular interactions, including C-H⋯π and N-H⋯π, but no direct hydrogen bonding.

Area of Science:

Crystallography
Organic Chemistry
Supramolecular Chemistry

Background:

Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
Aryl amines are common structural motifs in pharmaceuticals and materials science, making their structural characterization important.

Purpose of the Study:

To elucidate the detailed crystal structure of the title compound, C(12)H(10)BrN.
To analyze the spatial arrangement of the aryl rings and the nature of intermolecular interactions within the crystal lattice.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
Analysis of the crystal structure involved measuring dihedral and pitch angles and identifying non-covalent interactions.

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

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Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores

Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores

Published on: August 19, 2013

Main Results:

The dihedral angle between the benzene rings in C(12)H(10)BrN was determined to be 52.5°.
Pitch angles of 19.6° and 36.2° were observed between the aryl groups and the C-N-C plane.
The crystal structure is stabilized by intermolecular C-H⋯π and N-H⋯π interactions, with the N-H group not participating in hydrogen bonding.

Conclusions:

The non-planar conformation of the C(12)H(10)BrN molecule is quantified by specific dihedral and pitch angles.
The identified intermolecular interactions play a significant role in the crystal packing and stability of the compound.
This structural information provides a foundation for further studies on related compounds and their potential applications.