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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).

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...

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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...

Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles

Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles

Naming Amides
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.

Electrophilic Aromatic Substitution: Nitration of Benzene

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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.

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Updated: Jun 5, 2026

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

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2-Methyl-N-(3-methyl-phen-yl)benzamide.

B Thimme Gowda, Sabine Foro, B P Sowmya

Acta Crystallographica. Section E, Structure Reports Online

|January 5, 2011

Summary

This study details the crystal structure of N3MP2MBA, revealing specific bond conformations and hydrogen bonding patterns. The findings offer insights into benzanilide molecular structures and their crystal packing.

Area of Science:

Crystallography
Organic Chemistry
Molecular Structure

Background:

Benzanilides are an important class of organic compounds with diverse applications.
Understanding the molecular structure and crystal packing of benzanilides is crucial for predicting their properties and designing new materials.

Purpose of the Study:

To elucidate the detailed crystal structure of a novel benzanilide derivative, N3MP2MBA.
To analyze the conformational preferences and intermolecular interactions within the crystal lattice.

Main Methods:

Single-crystal X-ray diffraction analysis was performed on N3MP2MBA.
Bond parameters, dihedral angles, and hydrogen bonding networks were meticulously examined.

Main Results:

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The crystal structure of N3MP2MBA (C(15)H(15)NO) was determined.
Specific conformations of the N-H and C=O bonds were observed, relative to methyl substituents on the aniline and benzoyl rings, respectively.
The amide group exhibited a dihedral angle of 55.2(7)° with the benzoyl ring, and the inter-ring dihedral angle was 36.2(1)°.
N-H⋯O hydrogen bonds were identified, forming infinite chains along the b axis.

Conclusions:

The conformational analysis of N3MP2MBA provides valuable data for understanding structure-property relationships in benzanilides.
The observed hydrogen bonding pattern highlights the role of intermolecular forces in dictating crystal packing and stability.