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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.

Aromatic Hydrocarbon Anions: Structural Overview

Aromatic Hydrocarbon Anions: Structural Overview

Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous overlap of p...

Basicity of Aromatic Amines

Basicity of Aromatic Amines

The basicity of aromatic amines is much weaker than that of aliphatic amines due to the involvement of the lone pair of electrons over the N atom in resonance with the aryl rings. Generally, the electron-donating ability of any substituents on the aryl ring of aromatic amines increases the basicity of the amine by increasing electron density, and hence the availability of lone pair on the nitrogen. On the other hand, electron-withdrawing functional groups on the aryl ring of amines decrease the...

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.

Aromatic Hydrocarbon Cations: Structural Overview

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...

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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Related Experiment Video

Updated: Jun 1, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

2,4,6-Triphenyl-aniline.

Onome Ugono¹, Stephanie Cowin, Alicia M Beatty

¹Department of Chemistry and Biochemistry, Center for Nanoscience, University of Missouri-St. Louis, St. Louis, Missouri, USA.

Acta Crystallographica. Section E, Structure Reports Online

|May 19, 2011

Summary

Steric hindrance from bulky phenyl rings prevents hydrogen bonding in the C(24)H(19)N molecule. This structural feature influences molecular interactions and crystal packing in organic compounds.

Area of Science:

Organic Chemistry
Crystallography
Molecular Structure

Background:

Hydrogen bonding is a crucial intermolecular force influencing the physical and chemical properties of organic compounds.
Steric hindrance, caused by bulky substituents, can significantly impede or prevent intermolecular interactions like hydrogen bonding.
The title compound, C(24)H(19)N, possesses a structure with potential for steric crowding around the amine group.

Purpose of the Study:

To investigate the intermolecular interactions of the title compound, C(24)H(19)N.
To determine the role of steric bulk in the hydrogen-bonding capabilities of C(24)H(19)N.
To analyze the conformational preferences of the phenyl rings in relation to the central amine group.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular structure of C(24)H(19)N.

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Last Updated: Jun 1, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

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Analysis of intermolecular contacts within the crystal lattice to identify hydrogen-bonding events.

Measurement of dihedral angles between the central ring and pendant phenyl rings to quantify steric effects.

Main Results:

Individual molecules of C(24)H(19)N were observed to not participate in hydrogen-bonding interactions.
Significant steric bulk from the ortho-positioned phenyl rings effectively shields the amine nitrogen atom.
Dihedral angles between the central ring and pendant phenyl rings were measured as 68.26(10)°, 55.28(10)°, and 30.61(11)°.

Conclusions:

The steric bulk of the phenyl rings in C(24)H(19)N prevents intermolecular hydrogen bonding.
The observed dihedral angles reflect the conformational adjustments made to accommodate steric strain.
This lack of hydrogen bonding has implications for the compound's solid-state properties and reactivity.