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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.

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 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...

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.

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.

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 the...

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Updated: May 22, 2026

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphos^Ph Complexes

Published on: April 10, 2015

Ruthenium cryptates with an unusual selectivity for nitrate.

Naomi C A Baker¹, Nicholas C Fletcher, Peter N Horton

¹The School of Chemistry and Chemical Engineering, Queen's University Belfast, Belfast, UK BT9 5AG.

Dalton Transactions (Cambridge, England : 2003)

|May 2, 2012

Summary

Researchers synthesized two new ruthenium(II) tripodal complexes. The larger cavity complex showed decreased emission with halide and nitrate salts, indicating selective anion binding.

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Published on: August 23, 2018

Area of Science:

Coordination Chemistry
Supramolecular Chemistry
Ruthenium Complexes

Background:

Tripodal ligands offer unique coordination environments for metal ions.
Ruthenium complexes are widely studied for their diverse chemical and photophysical properties.

Purpose of the Study:

To synthesize and characterize novel ruthenium(II) tripodal complexes with varying cavity sizes.
To investigate the anion binding properties and spectroscopic responses of these complexes.

Main Methods:

Synthesis of two new tripodal ligands and their corresponding ruthenium(II) complexes.
Full characterization including X-ray structural determination.
Anion binding studies using spectroscopic methods (UV-Vis, fluorescence) and NMR titrations.

Main Results:

Successful synthesis and characterization of [Ru(L3)](PF(6))(2) and [Ru(L4)](PF(6))(2).
The smaller cavity complex showed moderate interactions with anions, precipitating dihydrogen phosphate.
The larger cavity complex exhibited decreased emission upon addition of chloride, bromide, hydrogen sulfate, and nitrate salts.
NMR titrations revealed a high binding affinity for nitrate in the larger cavity complex compared to halides.

Conclusions:

The cavity size and rigidity of tripodal ligands significantly influence their anion binding capabilities.
Ruthenium(II) complexes with expanded cavities can act as sensitive receptors for specific anions like nitrate.
These findings contribute to the development of novel anion sensing materials.