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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...

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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...

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Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

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Published on: January 19, 2016

Methyl 5-chloro-2-nitro-benzoate.

Yan-Shu Liang, Bing-Ni Liu, Mo Liu

Acta Crystallographica. Section E, Structure Reports Online

|December 27, 2011

Summary

This study details the crystal structure of C(8)H(6)ClNO(4), revealing twisted nitro and acetoxy groups. Molecular layers are formed via hydrogen bonds, with short intermolecular distances observed in the crystal packing.

Area of Science:

Crystallography
Organic Chemistry
Molecular Structure

Background:

Understanding the three-dimensional arrangement of atoms in organic molecules is crucial.
The influence of substituent groups on benzene ring planarity affects molecular properties.
Intermolecular interactions, such as hydrogen bonding, dictate crystal packing and solid-state behavior.

Purpose of the Study:

To elucidate the crystal structure of the compound C(8)H(6)ClNO(4).
To analyze the spatial arrangement and torsion angles of the nitro and acetoxy groups relative to the benzene ring.
To investigate the intermolecular interactions and packing motifs in the crystalline state.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.

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Published on: January 21, 2020

Analysis of bond lengths, bond angles, and torsion angles provided insights into molecular geometry.

Crystal structure visualization and analysis of intermolecular contacts were performed.

Main Results:

The crystal structure of C(8)H(6)ClNO(4) was successfully determined.
The nitro group exhibited a torsion angle of 29.4(1)°, and the acetoxy group showed a torsion angle of 49.7(1)° with respect to the benzene ring plane.
Weak C-H⋯O hydrogen bonds were identified, linking molecules into layers parallel to the (101) plane, with short intermolecular C⋯O distances of 2.925(3) Å.

Conclusions:

The compound C(8)H(6)ClNO(4) displays significant deviations from planarity due to the orientation of its substituents.
Hydrogen bonding plays a key role in organizing the molecules within the crystal lattice.
The observed crystal packing and intermolecular distances provide valuable data for understanding structure-property relationships in similar compounds.