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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.

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...

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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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

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3,4-Diamino-benzonitrile.

David K Geiger¹, Dylan E Parsons

¹Department of Chemistry, State University of New York-College at Geneseo, 1 College Circle, Geneseo, NY 14454, USA.

Acta Crystallographica. Section E, Structure Reports Online

|March 12, 2013

Summary

This summary is machine-generated.

The crystal structure of C7H7N3 features nearly coplanar non-hydrogen atoms. Hydrogen bonding between amine and nitrile groups forms a 3D network, revealing insights into molecular interactions.

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Area of Science:

Crystallography
Supramolecular Chemistry

Background:

Understanding molecular interactions is crucial in crystal engineering.
Hydrogen bonding plays a key role in dictating crystal packing and network formation.

Purpose of the Study:

To elucidate the crystal structure of the title molecule, C7H7N3.
To analyze the hydrogen bonding network within the crystal structure.

Main Methods:

Single-crystal X-ray diffraction was used to determine the molecular structure.
Analysis of intermolecular interactions, specifically hydrogen bonds, was performed.

Main Results:

The non-hydrogen atoms in C7H7N3 are nearly coplanar (r.m.s. deviation = 0.018 Å).
Two amine groups participate in N-H⋯N hydrogen bonds, acting as donors and acceptors.
Hydrogen bonding between amine and nitrile groups forms chains along [101].
These chains are interconnected by inter-amine hydrogen bonds, creating an infinite 3D network.

Conclusions:

The crystal structure of C7H7N3 is characterized by a robust 3D hydrogen-bonded network.
The observed network arises from specific N-H⋯N interactions between amine and nitrile functionalities.
This detailed structural analysis provides a foundation for understanding the material properties of C7H7N3.