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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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Published on: November 22, 2016

A PH-functionalized dicationic bis(imidazolio)diphosphine.

Mario Cicač-Hudi¹, Christoph M Feil¹, Nicholas Birchall¹

¹Institute of Inorganic Chemistry, University of Stuttgart, Pfaffenwaldring 55, 70550 Stuttgart, Germany. gudat@iac.uni-stuttgart.de.

Dalton Transactions (Cambridge, England : 2003)

|December 21, 2021

Summary

Researchers synthesized novel dicationic diphosphines and diphosphides using imidazolium-based precursors. These compounds, featuring bis(imidazolio) substitution, were characterized by X-ray diffraction and NMR spectroscopy.

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Published on: November 22, 2016

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Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology

Published on: May 15, 2012

Area of Science:

Organophosphorus Chemistry
Main Group Chemistry
Supramolecular Chemistry

Background:

Imidazolium salts are versatile precursors in coordination and organometallic chemistry.
Phosphine chemistry offers diverse bonding modes and reactivity.
The synthesis of multiply-cationic phosphorus compounds remains a synthetic challenge.

Purpose of the Study:

To explore the reactivity of secondary imidazolio-iodophosphines and imidazolio-phosphides.
To synthesize and characterize novel dicationic diphosphine species.
To investigate the stability and stereochemistry of these unique phosphorus compounds.

Main Methods:

Reaction of [(L)PHI]I with (L)PH in the presence of GaI3.
Spontaneous "dehalo-coupling" reactions.
Single-crystal X-ray diffraction for structural determination.
Nuclear Magnetic Resonance (NMR) spectroscopy for solution characterization.
Computational studies for stereochemical assignment and bonding analysis.

Main Results:

Isolation and characterization of a dicationic bis(imidazolio)-substituted dihydro-diphosphine, [(L)2P2H2][GaI4]2.
Observation of non-preparative formation of cationic diphosphines via dehalo-coupling.
Synthesis of a known (bis)imidazolio-diphosphide monocation, [(L)2P2H]+.
Identification of meso- and rac-diastereomers for the dicationic diphosphines in solution.
Confirmation of stereochemistry and elucidation of bonding through computational analysis.

Conclusions:

The reaction pathways provide access to novel dicationic diphosphine and diphosphide species.
The synthesized compounds exhibit interesting structural and stereochemical properties.
Computational studies offer valuable insights into the electronic structure and bonding of these cationic phosphorus systems.