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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...

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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.

Reactions at the Benzylic Position: Oxidation and Reduction

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The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.

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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...

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4-Nitro-phenyl 4-bromo-benzoate.

Rodolfo Moreno-Fuquen¹

¹Departamento de Química - Facultad de Ciencias, Universidad del Valle, Apartado 25360, Santiago de Cali, Colombia.

Acta Crystallographica. Section E, Structure Reports Online

|January 6, 2012

Summary

This summary is machine-generated.

This study reveals how C(13)H(8)BrNO(4) molecules form chains through hydrogen bonds and bromine-oxygen interactions. The crystal structure shows a twisted molecular conformation due to the arrangement of its aryl rings.

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Area of Science:

Crystallography
Chemical Physics

Background:

Understanding molecular interactions is key to materials science.
Crystal structure analysis provides insights into intermolecular forces.

Purpose of the Study:

To determine the crystal structure of C(13)H(8)BrNO(4).
To investigate intermolecular interactions and molecular conformation in the solid state.

Main Methods:

Single-crystal X-ray diffraction was used to analyze the crystal structure.
Analysis of hydrogen bonds and halogen bonds (Br...O contacts) was performed.

Main Results:

The crystal structure of C(13)H(8)BrNO(4) was elucidated.
Molecules are arranged in chains along the [101] direction.
Weak C-H⋯O hydrogen bonds and Br⋯O contacts (3.140(4) Å) mediate the chain formation.
A dihedral angle of 64.98(10)° between the nitrated and brominated aryl rings indicates a twisted molecular conformation.

Conclusions:

The crystal packing of C(13)H(8)BrNO(4) is governed by a combination of hydrogen bonding and halogen bonding.
The observed twist in the molecule is a significant structural feature affecting its solid-state arrangement.