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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.

Acids, Bases and Neutralization Reactions

Acids, Bases and Neutralization Reactions

An acid-base reaction is one in which a hydrogen ion, H+, is transferred from one chemical species to another. Such reactions are of central importance to numerous natural and technological processes, ranging from the chemical transformations within cells or lakes and oceans to the industrial-scale production of fertilizers, pharmaceuticals, and other substances essential to the society.

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO₂ Overview

Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by...

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO₂ Mechanism

Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.

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.

Weak Acid Solutions

Weak Acid Solutions

Few compounds act as strong acids. A far greater number of compounds behave as weak acids and only partially react with water, leaving a large majority of dissolved molecules in their original form and generating a relatively small amount of hydronium ions. Weak acids are commonly encountered in nature, being the substances partly responsible for the tangy taste of citrus fruits, the stinging sensation of insect bites, and the unpleasant smells associated with body odor. A familiar example of a...

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Related Experiment Video

Updated: Jun 26, 2025

Measurement of the Potential Rates of Dissimilatory Nitrate Reduction to Ammonium Based on 14NH4+/15NH4+ Analyses via Sequential Conversion to N2O

Measurement of the Potential Rates of Dissimilatory Nitrate Reduction to Ammonium Based on 14NH4+/15NH4+ Analyses via Sequential Conversion to N2O

Published on: October 7, 2020

Sustained bacterial N₂O reduction at acidic pH.

Guang He^1,2, Gao Chen^2,3, Yongchao Xie^2,4

¹Department of Biosystems Engineering and Soil Science, The University of Tennessee, Knoxville, Knoxville, TN, 37996, USA.

Nature Communications

|May 15, 2024

Summary

This summary is machine-generated.

Microbial nitrous oxide (N₂O) reduction occurs in acidic soils. A co-culture demonstrated N₂O consumption at pH 4.5, driven by interspecies nutritional exchange.

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Last Updated: Jun 26, 2025

Measurement of the Potential Rates of Dissimilatory Nitrate Reduction to Ammonium Based on 14NH4+/15NH4+ Analyses via Sequential Conversion to N2O

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Published on: October 7, 2020

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Published on: December 6, 2018

Medium Preparation for the Cultivation of Microorganisms under Strictly Anaerobic/Anoxic Conditions

Medium Preparation for the Cultivation of Microorganisms under Strictly Anaerobic/Anoxic Conditions

Published on: August 15, 2019

Area of Science:

Environmental microbiology
Biogeochemistry
Soil science

Background:

Nitrous oxide (N₂O) is a potent greenhouse gas with increasing emissions from agriculture.
Microbial N₂O reduction to N₂ is a key removal pathway, but often considered negligible in acidic environments.
Acidic soils contain nosZ genes, suggesting potential for N₂O reduction.

Purpose of the Study:

To investigate microbial N₂O reduction under acidic conditions.
To characterize a microbial co-culture from acidic tropical forest soil capable of N₂O reduction.
To elucidate the mechanisms and interactions enabling N₂O consumption in acidic environments.

Main Methods:

Isolation and cultivation of a microbial co-culture from acidic tropical forest soil.
Physiological characterization of N₂O reduction activity at low pH.
Integrated omics (genomics, transcriptomics, proteomics) and metabolic analyses.
Pyruvate fermentation and hydrogenotrophic N₂O reduction assays.

Main Results:

A co-culture, comprising Serratia sp. and Desulfosporosinus sp., effectively reduced N₂O at pH 4.5.
The co-culture exhibited bimodal growth, with Serratia sp. fermenting pyruvate and Desulfosporosinus sp. performing hydrogenotrophic N₂O reduction.
Interspecies interactions were identified, with Serratia sp. providing essential amino acids to Desulfosporosinus sp.
Growth-linked N₂O reduction was observed across a pH range of 4.5 to 6.

Conclusions:

Microbial N₂O reduction is feasible and significant in acidic soils.
Co-culture dynamics and interspecies nutritional exchange are crucial for N₂O consumption in acidic environments.
These findings highlight previously underestimated microbial N₂O mitigation potential in acidic ecosystems.