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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...

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.

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

Nucleophilic Aromatic Substitution: Addition–Elimination (S_NAr)

Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between the...

Acidity and Basicity of Alcohols and Phenols

Acidity and Basicity of Alcohols and Phenols

Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.

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...

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4-Nitro-phenyl 1-naphthoate.

Uzma Bibi, Humaira M Siddiqi, Zareen Akhter

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This summary is machine-generated.

This study details the crystal structure of a nitro-substituted aromatic compound. Molecular analysis reveals specific dihedral angles and intermolecular interactions, forming crystal chains.

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Area of Science:

Crystallography
Organic Chemistry
Materials Science

Background:

Understanding the three-dimensional arrangement of molecules in crystals is crucial for predicting material properties.
Aromatic compounds with nitro-substituents are important in various chemical applications.

Purpose of the Study:

To elucidate the detailed crystal structure of the title compound, C(17)H(11)NO(4).
To analyze the molecular conformation, including dihedral angles and substituent orientations.
To investigate intermolecular interactions driving crystal packing.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
Geometric parameters, including bond lengths, bond angles, and dihedral angles, were analyzed.
Intermolecular interactions, such as C-H⋯O contacts, were identified.

Main Results:

The crystal structure of C(17)H(11)NO(4) was determined.
A small dihedral angle of 8.66(3)° was observed between the two benzene rings.
The nitro group exhibited a twist of 4.51(9)° relative to its attached aromatic ring.
Intermolecular C-H⋯O contacts were identified as the primary driving force for chain formation along the c axis.

Conclusions:

The crystal structure provides precise geometric data for the title compound.
The observed molecular conformation and intermolecular interactions dictate the solid-state packing.
The formation of 1D chains via C-H⋯O contacts is a key feature of this crystal structure.