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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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Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.

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Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...

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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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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.

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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4-Bromo-phenyl benzoate.

B Thimme Gowda, Sabine Foro, K S Babitha

Acta Crystallographica. Section E, Structure Reports Online

|January 5, 2011

Summary

This summary is machine-generated.

The crystal structure of 4-bromophenyl benzoate (4BPBA) was determined and compared to similar benzoate compounds. Its molecular packing reveals infinite chains along the a-axis.

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Area of Science:

Crystallography
Organic Chemistry
Materials Science

Background:

Benzoate esters are a class of organic compounds with diverse applications.
Understanding the structure-property relationships of substituted benzoates is crucial for materials design.
Previous studies have characterized phenyl benzoate (PBA) and its derivatives.

Purpose of the Study:

To determine the crystal structure of 4-bromophenyl benzoate (4BPBA).
To compare the structural parameters of 4BPBA with related benzoate compounds.
To investigate the molecular packing arrangement of 4BPBA.

Main Methods:

Single-crystal X-ray diffraction was employed to elucidate the molecular structure.
Crystallographic data were analyzed to determine bond lengths, bond angles, and dihedral angles.
Crystal structure analysis was performed to understand the intermolecular interactions and packing motifs.

Main Results:

The crystal structure of 4-bromophenyl benzoate (C(13)H(9)BrO(2)) was successfully determined.
The dihedral angle between the phenyl and benzoyl rings in 4BPBA is 58.43(17)°, which is comparable to PBA (55.7°) and 4-methylphenyl benzoate (4MPBA) (60.17(7)°).
Molecules of 4BPBA are arranged in infinite chains along the a-axis direction.

Conclusions:

4BPBA exhibits structural similarities to other benzoate esters, with slight variations in bond parameters.
The dihedral angle provides insight into the conformational flexibility of the benzoate ester linkage.
The observed chain packing suggests potential for anisotropic properties in solid-state applications.