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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...

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.

Reactions at the Benzylic Position: Halogenation

Reactions at the Benzylic Position: Halogenation

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

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

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...

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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.

Radical Substitution: Allylic Bromination

Radical Substitution: Allylic Bromination

In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...

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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

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1-Bromo-4-methyl-2-nitro-benzene.

Ping Li¹, Hai Wang, Ximan Zhang

¹School of Chemistry and Chemical Engineering, TaiShan Medical University, Tai'an 271016, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|November 8, 2011

Summary

This study details the crystal structure of a novel bromo-nitro-phenyl compound. Analysis reveals a specific dihedral angle between the nitro group and the phenyl ring, offering insights into molecular geometry.

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Area of Science:

Crystallography
Organic Chemistry
Molecular Structure

Background:

Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
Bromo-nitro-phenyl compounds are of interest due to their potential applications in materials science and medicinal chemistry.

Purpose of the Study:

To determine the precise molecular geometry of the title compound, C(7)H(6)BrNO(2).
To quantify the spatial relationship between the nitro group and the phenyl ring within the crystal structure.

Main Methods:

Single-crystal X-ray diffraction was employed to analyze the crystal structure of C(7)H(6)BrNO(2).
Crystallographic data were collected and refined to obtain precise atomic coordinates and bond parameters.

Main Results:

The crystal structure of C(7)H(6)BrNO(2) was successfully elucidated.
The dihedral angle between the nitro group and the phenyl ring was determined to be 14.9(11)°.

Conclusions:

The determined dihedral angle provides a quantitative measure of the non-planarity between the nitro substituent and the phenyl core.
This structural information contributes to the understanding of substituent effects on aromatic ring conformation in organic solids.