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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...

IUPAC Nomenclature of Aldehydes

IUPAC Nomenclature of Aldehydes

Aldehydes are named based on the systematic nomenclature rules set by the IUPAC. For acyclic aldehydes, the longest carbon chain containing the aldehydic (–CHO) group is considered the parent chain. The aldehyde is named by replacing the last letter “e” in the hydrocarbon name with “al”. For instance, a simple, seven-carbon-membered acyclic aldehyde is called heptanal, derived from heptane. The carbon chain is numbered starting from the aldehydic carbon, although the aldehydic carbon’s locant...

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.

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...

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Related Experiment Video

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Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

Published on: November 15, 2017

2-Methyl-3,5-dinitro-benzoic acid.

M Nawaz Tahir, Abdul Rauf Raza, Aisha Saddiqa

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This summary is machine-generated.

The crystal structure of a nitrobenzoic acid derivative reveals significant molecular disorder in its nitro, methyl, and carboxyl groups. These structural complexities are stabilized by hydrogen bonding and other weak intermolecular interactions.

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Area of Science:

Crystallography
Organic Chemistry
Materials Science

Background:

Understanding molecular structure and disorder is crucial in crystal engineering.
Nitrobenzoic acid derivatives are important in various chemical applications.
Disorder in crystalline structures can significantly impact material properties.

Purpose of the Study:

To elucidate the crystal structure of the title compound, C(8)H(6)N(2)O(6).
To investigate the nature and extent of molecular disorder within the crystal lattice.
To analyze the intermolecular interactions responsible for crystal packing.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
Analysis of atomic coordinates and occupancy factors revealed the disorder.
Hydrogen bonding and other non-covalent interactions were identified using crystallographic analysis.

Main Results:

The crystal structure exhibits disorder in the oxygen atoms of the nitro groups, methyl hydrogen atoms, and carboxyl groups (C=O and C-OH).
The disorder involves two sets of atomic sites with an occupancy ratio of approximately 0.595:0.405.
Inversion dimers formed by O-H⋯O hydrogen bonds were observed for both carboxyl disorder components.
Crystal packing is further stabilized by C-H⋯O bonds and weak C-H⋯π interactions.

Conclusions:

The title compound displays significant positional disorder in key functional groups.
Intermolecular hydrogen bonding and weaker interactions play a vital role in stabilizing the disordered crystal structure.
The findings provide insights into the structural behavior of nitrobenzoic acid derivatives and their packing motifs.