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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.

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...

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...

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.

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.

Nitrosation of Enols

Nitrosation of Enols

The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

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2,3-Bis(4-nitrobenzylthio)maleonitrile

¹Coordination Chemistry Institute and State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, People's Republic of China.

Acta Crystallographica. Section C, Crystal Structure Communications

|December 19, 2000

Summary

The crystal structure of (2Z)-2,3-bis[(4-nitrobenzyl)sulfanyl]but-2-enedinitrile reveals a nearly planar maleonitrile core. This study highlights intermolecular sulfur-sulfur and pi-pi interactions in the solid state.

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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

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Published on: January 21, 2020

Area of Science:

Crystallography
Organic Chemistry
Supramolecular Chemistry

Background:

The title compound, (2Z)-2,3-bis[(4-nitrobenzyl)sulfanyl]but-2-enedinitrile, possesses a unique molecular architecture.
Understanding the solid-state packing and intermolecular interactions is crucial for predicting material properties.

Purpose of the Study:

To elucidate the crystal structure of (2Z)-2,3-bis[(4-nitrobenzyl)sulfanyl]but-2-enedinitrile.
To investigate the nature and significance of intermolecular interactions, specifically sulfur-sulfur (S-S) and pi-pi stacking.

Main Methods:

Single-crystal X-ray diffraction analysis was employed to determine the three-dimensional molecular structure.
Analysis of the crystal packing revealed the spatial arrangement of molecules and the presence of specific intermolecular contacts.

Main Results:

The maleonitrile moiety of the compound exhibits a near-planar conformation.
The two 4-nitrobenzyl groups are positioned nearly parallel to each other and perpendicular to the maleonitrile plane.
Significant intermolecular S-S and pi-pi interactions were identified in the crystal lattice.

Conclusions:

The crystal structure provides detailed insights into the solid-state behavior of (2Z)-2,3-bis[(4-nitrobenzyl)sulfanyl]but-2-enedinitrile.
The observed intermolecular interactions likely influence the compound's physical properties and potential applications.