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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.

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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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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

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2,4,6-trifluorobenzonitrile.

Doyle Britton¹

¹Department of Chemistry, University of Minnesota, Minneapolis, MN 55455-0431, USA. britton@umn.edu

Acta Crystallographica. Section C, Crystal Structure Communications

|November 8, 2008

Summary

This summary is machine-generated.

This study reveals the unique crystal structure of a trifluorinated benzonitrile compound. It highlights the presence of multiple distinct interlayer interactions, offering insights into molecular packing and intermolecular forces.

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Area of Science:

Crystal Engineering
Solid-State Chemistry
Supramolecular Chemistry

Background:

Understanding molecular packing is crucial for designing materials with specific properties.
Benzonitrile derivatives are widely studied for their electronic and structural characteristics.
Intermolecular interactions dictate the assembly and properties of crystalline solids.

Purpose of the Study:

To elucidate the crystal structure of the title compound, C(7)H(2)F(3)N.
To analyze the types and characteristics of interlayer contacts within the crystal lattice.
To compare the observed packing motifs with related difluorobenzonitrile compounds.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the three-dimensional crystal structure.
Analysis of crystallographic data identified independent molecules and their symmetries (m and mm).
Intermolecular interactions, specifically C-H...N hydrogen bonds, were investigated.

Main Results:

The crystal structure contains three crystallographically independent molecules, two with m symmetry and one with mm symmetry.
Each molecule type forms planar or approximately planar layers.
Three distinct types of interlayer contacts were identified, with two being similar and one notably different.
Intralayer packing resembles that of 2,5- and 3,6-difluorobenzonitrile, stabilized by C-H...N interactions.

Conclusions:

The crystal structure of C(7)H(2)F(3)N exhibits complex layering and diverse interlayer interactions.
The presence of multiple, distinct interlayer contact types is a key feature of this structure.
This finding contributes to the understanding of crystal engineering principles and structure-property relationships in fluorinated aromatic compounds.