Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

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 water loss...

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.

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.

Preparation of Amines: Alkylation of Ammonia and Amines

Preparation of Amines: Alkylation of Ammonia and Amines

Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...

Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia

Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia

Alkynes can be reduced to trans-alkenes using sodium or lithium in liquid ammonia. The reaction, known as dissolving metal reduction, proceeds with an anti addition of hydrogen across the carbon–carbon triple bond to form the trans product. Since ammonia exists as a gas (bp = −33°C) at room temperature, the reaction is carried out at low temperatures using a mixture of dry ice (sublimes at −78°C) and acetone.
When dissolved in liquid ammonia, an alkali metal, such as sodium, dissociates into a...

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by

Same author

The Pschorr Reaction: Recent Advances and Application in Heterocyclic Synthesis.

Molecules (Basel, Switzerland)·2026

Same author

Editorial: Spotlight on North America - chemical sciences.

Frontiers in chemistry·2024

Same author

Recent Advances in the Synthesis of Organic Thiocyano (SCN) and Selenocyano (SeCN) Compounds, Their Chemical Transformations and Bioactivity.

Molecules (Basel, Switzerland)·2024

Same author

Recent Advances in the Synthesis of Propargyl Derivatives, and Their Application as Synthetic Intermediates and Building Blocks.

Molecules (Basel, Switzerland)·2023

Same author

Design, synthesis, and molecular docking study of novel quinoline-based bis-chalcones as potential antitumor agents.

Archiv der Pharmazie·2021

Same author

Curcumin Conjugates of Non-steroidal Anti-Inflammatory Drugs: Synthesis, Structures, Anti-proliferative Assays, Computational Docking, and Inflammatory Response.

ChemistryOpen·2020

Search research articles

Related Experiment Video

Updated: May 30, 2026

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

Ethylammonium nitrate (EAN)/Tf2O and EAN/TFAA: ionic liquid based systems for aromatic nitration.

Gopalakrishnan Aridoss¹, Kenneth K Laali

¹Department of Chemistry, University of North Florida, 1 UNF Drive, Jacksonville, Florida 32224, United States.

The Journal of Organic Chemistry

|August 25, 2011

Summary

New nitrating systems using ethylammonium nitrate (EAN) ionic liquid efficiently generate triflyl nitrate and trifluoroacetyl nitrate for electrophilic aromatic nitration. EAN/Tf(2)O shows superior performance for deactivated compounds.

More Related Videos

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Published on: January 3, 2018

Related Experiment Videos

Last Updated: May 30, 2026

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Published on: January 3, 2018

Area of Science:

Organic Chemistry
Green Chemistry
Nitration Reactions

Background:

Electrophilic aromatic substitution is a fundamental organic reaction.
Developing efficient and selective nitrating agents is crucial for synthesizing complex molecules.
Ionic liquids offer unique solvent properties for chemical transformations.

Purpose of the Study:

To develop novel in situ nitrating reagents using ethylammonium nitrate (EAN) ionic liquid.
To evaluate the efficacy of triflyl nitrate (TfONO(2)) and trifluoroacetyl nitrate (CF(3)COONO(2)) generated in EAN for nitration.
To compare the performance of EAN/Tf(2)O and EAN/TFAA systems, particularly for deactivated substrates.

Main Methods:

Generation of TfONO(2) and CF(3)COONO(2) via metathesis reactions within the EAN ionic liquid.
Electrophilic nitration of diverse aromatic and heteroaromatic compounds using the in situ generated reagents.
Comparative studies to assess the reactivity and selectivity of the EAN/Tf(2)O and EAN/TFAA systems.
Determination of substrate selectivity using kinetic measurements (K(T)/K(B)).

Main Results:

The EAN/Tf(2)O and EAN/TFAA systems effectively act as in situ sources of potent electrophilic nitrating agents.
Both systems demonstrate broad applicability for nitrating a wide range of aromatic and heteroaromatic compounds.
The EAN/Tf(2)O system exhibits enhanced performance compared to EAN/TFAA when nitrating strongly deactivated aromatic systems.
Both nitrating systems display low substrate selectivity, with K(T)/K(B) values ranging from 5-10.

Conclusions:

Ethylammonium nitrate-based systems provide a convenient and effective method for generating triflyl nitrate and trifluoroacetyl nitrate in situ.
These novel nitrating reagents offer a powerful approach for electrophilic nitration of various organic substrates.
The EAN/Tf(2)O system is particularly advantageous for the nitration of challenging, deactivated aromatic compounds.