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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.

Basicity of Heterocyclic Aromatic Amines

Basicity of Heterocyclic Aromatic Amines

Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).

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...

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.

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.

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.

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Related Experiment Video

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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-pyridylmeth-yl)aniline.

Jun-Tao Kang¹, Guan-Hua Wang, Jing-Wei Xu

¹The State Key Laboratory of Electroanalytical Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This study analyzes the molecular structure of C(18)H(17)N(3), revealing specific dihedral angles between its phenyl and pyridyl rings. Crystal analysis identified weak intermolecular C-H⋯π interactions.

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Area of Science:

Organic Chemistry
Crystallography

Background:

Understanding the three-dimensional structure of organic molecules is crucial for predicting their properties and reactivity.
Dihedral angles define the spatial arrangement of atoms within a molecule, influencing its overall conformation.

Purpose of the Study:

To determine the precise molecular geometry of the title compound, C(18)H(17)N(3).
To investigate intermolecular interactions within the crystal lattice.

Main Methods:

Single-crystal X-ray diffraction was employed to analyze the crystal structure.
Geometric parameters, including dihedral angles, were precisely measured.

Main Results:

The two pyridyl rings exhibit a dihedral angle of 54.55°.
The phenyl ring forms dihedral angles of 73.61° and 81.40° with the two pyridyl rings.
Weak intermolecular C-H⋯π interactions were observed in the crystal packing.

Conclusions:

The study provides detailed structural information for C(18)H(17)N(3).
The observed dihedral angles indicate a non-planar molecular conformation.
Intermolecular C-H⋯π interactions play a role in the crystal packing of this compound.