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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.

ortho–para-Directing Activators: –CH3, –OH, –&NoBreak;NH2, –OCH3

ortho–para-Directing Activators: –CH₃, –OH, –⁠NH₂, –OCH₃

All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...

NMR Spectroscopy of Benzene Derivatives

NMR Spectroscopy of Benzene Derivatives

Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling constants depend...

Nucleophilic Aromatic Substitution: Elimination–Addition

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...

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Updated: May 27, 2026

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

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

Published on: January 21, 2020

Isopropyl 4-nitro-benzoate.

Pei Zou¹, Min-Hao Xie, Hao Wu

¹Jiangsu Institute of Nuclear Medicine, Wuxi 214063, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|November 8, 2011

Summary

This summary is machine-generated.

This study details the molecular structure of C(10)H(11)NO(4), revealing a nitro group nearly aligned with the benzene ring and a twisted carboxylate group. Crystal analysis identified weak C-H⋯O hydrogen bonds and π-π stacking interactions.

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

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Area of Science:

Crystallography
Organic Chemistry
Molecular Structure Analysis

Background:

Understanding the precise three-dimensional arrangement of atoms in organic molecules is crucial for predicting their chemical behavior and physical properties.
Intermolecular interactions, such as hydrogen bonding and π-π stacking, significantly influence crystal packing and material characteristics.

Purpose of the Study:

To elucidate the detailed molecular geometry of the title compound, C(10)H(11)NO(4).
To investigate the intermolecular interactions present in the crystalline state of the compound.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular structure.
Analysis of crystallographic data was performed to identify and quantify dihedral angles and intermolecular contacts.

Main Results:

The nitro group exhibits approximate coplanarity with the benzene ring (dihedral angle = 4.57°).
The carboxylate group is slightly twisted relative to the benzene ring (angle = 12.16°).
Weak intermolecular C-H⋯O hydrogen bonds and π-π stacking interactions (centroid-centroid distances of 3.670(2) Å and 3.665(2) Å) were observed in the crystal.

Conclusions:

The specific orientation of the nitro and carboxylate groups influences the molecule's conformation.
The identified intermolecular interactions dictate the crystal packing and stability of the compound.