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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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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.

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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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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...

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Published on: January 19, 2016

N'-(2-Fluoro-benzo-yl)benzohydrazide.

Krzysztof Ejsmont, Muhammad Zareef, Muhammad Arfan

Acta Crystallographica. Section E, Structure Reports Online

|January 5, 2011

Summary

The crystal structure of C(14)H(11)FN(2)O(2) reveals a centrosymmetric molecule with disordered fluorine atoms. Intermolecular hydrogen bonds link molecules in the crystal lattice, influencing crystal packing.

Area of Science:

Crystallography
Materials Science
Organic Chemistry

Background:

Understanding molecular arrangements in crystals is crucial for predicting material properties.
The specific compound C(14)H(11)FN(2)O(2) has not been extensively studied in terms of its solid-state structure.
Fluorine's unique electronic properties can significantly impact molecular conformation and intermolecular interactions.

Purpose of the Study:

To elucidate the crystal structure of the title compound, C(14)H(11)FN(2)O(2).
To investigate the molecular symmetry and the behavior of the fluorine atom within the crystal lattice.
To identify and characterize the intermolecular interactions present in the crystal structure.

Main Methods:

Single-crystal X-ray diffraction was employed to collect diffraction data.

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The crystal structure was solved and refined using standard crystallographic software.

Analysis of bond lengths, bond angles, and intermolecular contacts was performed.

Main Results:

The title compound C(14)H(11)FN(2)O(2) crystallizes in a centrosymmetric molecular arrangement.
The fluorine atom exhibits disorder, occupying four distinct positions with specific occupancies.
Intermolecular hydrogen bonds, specifically N-H⋯O and C-H⋯O, were identified as key interactions mediating crystal packing.

Conclusions:

The detailed crystal structure of C(14)H(11)FN(2)O(2) has been determined.
The observed fluorine disorder and hydrogen bonding patterns provide insights into the solid-state behavior of this fluorinated organic molecule.
This structural information can serve as a foundation for further studies on structure-property relationships.