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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.

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.

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.

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...

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic S_N1

Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...

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Preparation of SNS Cobalt(II) Pincer Model Complexes of Liver Alcohol Dehydrogenase

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Published on: March 19, 2020

Bis(4-amino-benzoic acid-κN)dichloridozinc(II).

Melanie Rademeyer¹, Gerhard E Overbeek, David C Liles

¹Department of Chemistry, University of Pretoria, Pretoria 0002, South Africa.

Acta Crystallographica. Section E, Structure Reports Online

|May 19, 2011

Summary

This study details the crystal structure of a zinc compound with 4-amino-benzoic acid. The molecules form a 3D network through hydrogen bonding, revealing intricate molecular interactions.

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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

Area of Science:

Coordination Chemistry
Crystal Engineering
Materials Science

Background:

Understanding the self-assembly of metal-organic compounds is crucial for designing new materials.
4-amino-benzoic acid is a versatile ligand with potential applications in coordination chemistry.
Zinc chloride complexes offer tunable properties for various applications.

Purpose of the Study:

To elucidate the crystal structure and supramolecular assembly of the [ZnCl2(C7H7NO2)2] complex.
To investigate the role of hydrogen bonding in the formation of a three-dimensional network.
To characterize the coordination environment around the zinc(II) ion.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
Analysis of intermolecular interactions, including hydrogen bonds (O-H...O, N-H...Cl), was performed.
The coordination geometry and network topology were investigated.

Main Results:

The crystal structure reveals a discrete tetrahedral zinc(II) complex, [ZnCl2(C7H7NO2)2].
Molecules are interconnected via hydrogen bonds involving carboxyl groups and amine groups.
A robust three-dimensional supramolecular network is formed through N-H...Cl and O-H...O hydrogen bonding interactions.

Conclusions:

The compound forms an extended 3D network driven by specific hydrogen bonding motifs.
The tetrahedral coordination geometry around zinc is confirmed.
This study provides insights into the crystal engineering of zinc-based coordination compounds.