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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.

Diazonium Group Substitution: –OH and –H

Diazonium Group Substitution: –OH and –H

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.

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...

Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene

Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene

The Friedel–Crafts acylation reactions involve the addition of an acyl group to an aromatic ring. These reactions proceed via electrophilic aromatic substitution by employing an acyl chloride and a Lewis acid catalyst such as aluminum chloride to form aryl ketone.

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Updated: Jun 5, 2026

[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

[(DPEPhos)(bcp)Cu]PF₆: A General and Broadly Applicable Copper-Based Photoredox Catalyst

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Diaqua-bis(benzyl-oxyacetato)copper(II).

Sheng-Li Sun, Chun-Liang Chen, Chang-Sheng Gu

Acta Crystallographica. Section E, Structure Reports Online

|January 5, 2011

Summary

This study details a mononuclear copper(II) complex, [Cu(C(9)H(9)O(3))(2)(H(2)O)(2)], featuring a distorted octahedral geometry. The crystal structure reveals intermolecular hydrogen bonds forming layered networks.

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Synthesis of Triazole and Tetrazole-Functionalized Zr-Based Metal-Organic Frameworks Through Post-Synthetic Ligand Exchange

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Synthesis of Triazole and Tetrazole-Functionalized Zr-Based Metal-Organic Frameworks Through Post-Synthetic Ligand Exchange

Synthesis of Triazole and Tetrazole-Functionalized Zr-Based Metal-Organic Frameworks Through Post-Synthetic Ligand Exchange

Published on: June 23, 2023

Area of Science:

Inorganic Chemistry
Crystallography
Coordination Chemistry

Background:

Copper(II) complexes are widely studied for their diverse structural motifs and potential applications.
Benzyl-oxyacetate ligands offer interesting coordination possibilities due to their functional groups.
Understanding the coordination environment and crystal packing is crucial for predicting material properties.

Purpose of the Study:

To synthesize and characterize a novel mononuclear copper(II) complex.
To elucidate the coordination geometry and crystal structure of the synthesized complex.
To investigate the intermolecular interactions governing the crystal packing.

Main Methods:

Single crystal X-ray diffraction was employed to determine the molecular and crystal structure.
The coordination environment around the central Cu(II) ion was analyzed.
Intermolecular interactions, specifically hydrogen bonding, were identified and characterized.

Main Results:

A mononuclear copper(II) complex, [Cu(C(9)H(9)O(3))(2)(H(2)O)(2)], was successfully synthesized and characterized.
The Cu(II) ion is hexa-coordinated in a distorted octahedral geometry, bonded to four oxygen atoms from two benzyl-oxyacetate ligands and two water molecules.
Crystal structure analysis revealed the formation of layered networks through intermolecular O-H⋯O hydrogen bonds parallel to the bc plane.

Conclusions:

The synthesized mononuclear copper(II) complex exhibits a distorted octahedral coordination geometry.
Intermolecular hydrogen bonding plays a significant role in organizing the crystal structure into layered arrangements.
The study provides insights into the structural characteristics of copper(II) complexes with benzyl-oxyacetate ligands.