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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.

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.

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...

Amines: Introduction

Amines: Introduction

Amines are organic derivatives of ammonia. They are formed by replacing one or more ammonia protons with alkyl or aryl groups. Depending upon the number of organyl groups bonded to nitrogen, amines are classified as primary, secondary, or tertiary. Primary amines have one organyl group attached to the nitrogen atom, while secondary and tertiary amines have two and three organyl groups attached to the nitrogen atom, respectively.

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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Updated: Jan 18, 2026

A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s

A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s

Published on: September 25, 2017

5-Methyl-2-nitro-aniline.

Lily Samson¹, Lydia Banwart¹, Sajan Silwal¹

¹Department of Chemistry and Physics Southeast Missouri State University,Cape Girardeau MO 63701 USA.

|September 8, 2025

Summary

This summary is machine-generated.

This study analyzes the molecular structure of a 5-substituted-2-nitro-aniline derivative. Findings reveal specific bond lengths and angles, and N-H⋯O hydrogen bonds forming intricate molecular tapes and ribbons.

Keywords:

DFT geometry optimization crystal structure hydrogen bonding

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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

Area of Science:

Crystallography
Organic Chemistry
Materials Science

Background:

5-substituted-2-nitro-anilines are a class of organic compounds with potential applications.
Understanding their precise molecular geometry and intermolecular interactions is crucial for predicting material properties.

Purpose of the Study:

To determine the crystal structure and molecular geometry of a specific 5-substituted-2-nitro-aniline derivative.
To investigate the intermolecular interactions, specifically hydrogen bonding, that govern the self-assembly of these molecules.

Main Methods:

Single-crystal X-ray diffraction was employed to elucidate the three-dimensional structure.
Density Functional Theory (DFT) calculations were performed for geometry optimization and comparison.

Main Results:

The molecule's bond lengths and angles are consistent with average values for related compounds and DFT calculations.
A notably short C-NH2 bond length (1.3469(12) Å) indicates significant aniline N-atom participation in the aromatic π-system.
N-H⋯O hydrogen bonds facilitate the formation of [001] tapes, which further assemble into zipper-like folded ribbons, ultimately forming layered structures.

Conclusions:

The crystal structure of the studied nitro-aniline derivative has been determined.
The observed hydrogen bonding network dictates the formation of extended supramolecular architectures.
The electronic structure, particularly the π-system involvement, influences the molecular geometry.