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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.

meta-Directing Deactivators: –NO2, –CN, –CHO, –&NoBreak;CO2R, –COR, –CO2H

meta-Directing Deactivators: –NO₂, –CN, –CHO, –⁠CO₂R, –COR, –CO₂H

All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...

Preparation of Nitriles

Preparation of Nitriles

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...

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.

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...

ortho–para-Directing Activators: –CH3, –OH, –&NoBreak;NH2, –OCH3

ortho–para-Directing Activators: –CH₃, –OH, –⁠NH₂, –OCH₃

All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...

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Updated: Mar 31, 2026

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

Copper(II) mediated phenol ring nitration by nitrogen dioxide.

Vikash Kumar¹, Somnath Ghosh¹, Anoop Kumar Saini²

¹Department of Chemistry, Indian Institute of Technology Guwahati, Assam 781039, India. biplab@iitg.ernet.in.

Dalton Transactions (Cambridge, England : 2003)

|October 31, 2015

Summary

This summary is machine-generated.

Copper(II) complexes with N2O2 ligands undergo selective nitration on equatorial phenolate rings upon reaction with nitrogen dioxide. This reaction pathway involves the formation of phenoxyl radical intermediates, highlighting unique reactivity in coordinated ligand systems.

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Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

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Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

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Area of Science:

Coordination Chemistry
Organic Synthesis
Spectroscopy

Background:

N2O2 type ligands are crucial in coordinating metal ions, influencing their reactivity.
Copper(II) complexes exhibit diverse catalytic and reactive properties.
Understanding ligand modification in metal complexes is key to designing new materials.

Purpose of the Study:

To synthesize and characterize novel Cu(II) complexes with N2O2 ligands.
To investigate the reactivity of these complexes towards nitrogen dioxide.
To elucidate the mechanism of ligand nitration in coordinated systems.

Main Methods:

Synthesis of Cu(II) complexes with L(1)H2 and L(2)H2 ligands.
Reaction of complexes with nitrogen dioxide in Tetrahydrofuran (THF).
Spectroscopic analysis (e.g., UV-Vis, EPR) to characterize products and intermediates.

Main Results:

Selective nitration occurred at the 4-position of the equatorial phenolate ring.
Axially coordinated phenol rings remained unreacted.
Spectroscopic data indicated the formation of phenoxyl radical complexes during nitration.

Conclusions:

Cu(II) complexes with N2O2 ligands show regioselective nitration under NO2 exposure.
The equatorial phenolate rings are preferentially functionalized.
The reaction mechanism likely involves a phenoxyl radical intermediate, offering insights into redox processes in coordination chemistry.