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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).

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...

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.

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 Multiple Substituents

Nomenclature of Aromatic Compounds with Multiple Substituents

When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...

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Related Experiment Video

Updated: Jun 5, 2026

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

Published on: November 23, 2016

N-(2,6-Dimethyl-phen-yl)benzamide.

B Thimme Gowda, Miroslav Tokarčík, Jozef Kožíšek

Acta Crystallographica. Section E, Structure Reports Online

|January 5, 2011

Summary

This study details the crystal structure of a benzanilide derivative, C(15)H(15)NO. The research reveals specific molecular conformations and hydrogen bonding patterns, contributing to understanding crystalline organic compounds.

Area of Science:

Crystallography
Organic Chemistry
Solid-State Chemistry

Background:

Benzanilides are a significant class of organic compounds with diverse applications.
Understanding the solid-state structure of benzanilides is crucial for predicting their physical and chemical properties.

Purpose of the Study:

To elucidate the crystal structure of the title compound, C(15)H(15)NO.
To analyze the molecular conformation, including the orientation of the benzoyl and aniline rings and the amide linkage.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
Analysis of bond lengths, bond angles, dihedral angles, and intermolecular interactions (hydrogen bonds).

Main Results:

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The title compound crystallizes with two molecules in the asymmetric unit.
The H-N-C=O amide units adopt a trans conformation.
The benzoyl and aniline rings are nearly orthogonal, with dihedral angles around 86°.
N-H⋯O hydrogen bonds form infinite chains along the c axis.

Conclusions:

The crystal structure of C(15)H(15)NO exhibits specific conformational preferences and intermolecular hydrogen bonding.
These structural features are comparable to other substituted benzanilides.
The findings contribute to the structure-property relationships in benzanilide derivatives.