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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.

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...

Nomenclature of Aromatic Compounds with a Single Substituent

Nomenclature of Aromatic Compounds with a Single Substituent

Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).

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.

Structure of Benzene: Molecular Orbital Model

Structure of Benzene: Molecular Orbital Model

According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).

Electrophilic Aromatic Substitution: Sulfonation of Benzene

Electrophilic Aromatic Substitution: Sulfonation of Benzene

Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.

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Updated: May 17, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

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Benzyl-ammonium hexa-noate.

Mary H Wood¹, Stuart M Clarke

¹BP Institute and Department of Chemistry, University of Cambridge, Cambridge, England.

Acta Crystallographica. Section E, Structure Reports Online

|November 6, 2012

Summary

Researchers formed a novel salt from benzyl-amine and hexa-noic acid. This 1:1 crystal structure, with complete proton transfer and unique hydrogen bonding, differs from related compounds.

Area of Science:

Crystallography
Supramolecular Chemistry
Organic Chemistry

Background:

Amine-acid salts are crucial in various chemical applications.
The stoichiometry and hydrogen bonding in these salts influence their properties.
Previous studies show varied stoichiometric ratios in related systems.

Purpose of the Study:

To synthesize and characterize a novel salt formed from benzyl-amine and hexa-noic acid.
To investigate the proton transfer and hydrogen bonding characteristics of the resulting crystal.
To compare the structural features with related amine-acid salts.

Main Methods:

Single crystal X-ray diffraction was employed to determine the crystal structure.
Stoichiometry and proton transfer were analyzed from diffraction data.

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A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products

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Hydrogen bonding networks were examined.

Main Results:

A 1:1 salt, C(7)H(10)N(+)·C(6)H(11)O(2) (-), was successfully formed.
Complete proton transfer from hexa-noic acid to benzyl-amine was confirmed.
Each ammonium group is involved in three hydrogen bonds, forming a distinct structural motif.

Conclusions:

The synthesized salt exhibits a unique 1:1 stoichiometry, differing from other known integer ratios.
The observed hydrogen bonding pattern around the ammonium groups is a key structural feature.
This study provides insights into the formation and structural diversity of amine-acid salts.