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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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Updated: Jun 1, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

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Published on: November 22, 2016

3-Carbamothioylpyridinium iodide.

Shahzad Sharif, Mehmet Akkurt, Islam Ullah Khan

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This study reveals the crystal structure of a sulfur-containing organic salt. Hydrogen bonds link the molecules and ions into zigzag chains, providing insights into crystal packing and intermolecular interactions.

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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

Area of Science:

Crystallography
Chemical Physics
Materials Science

Background:

Understanding the crystal structure of organic salts is crucial for predicting their physical and chemical properties.
Hydrogen bonding plays a significant role in molecular self-assembly and the formation of extended structures in the solid state.

Purpose of the Study:

To determine and describe the crystal structure of the title organic salt, C(6)H(7)N(2)S(+)·I(-).
To investigate the role of hydrogen bonding in the self-assembly of cations and anions within the crystal lattice.

Main Methods:

Single-crystal X-ray diffraction was employed to elucidate the three-dimensional crystal structure.
Analysis of intermolecular interactions, specifically hydrogen bonds (N-H⋯S and N-H⋯I), was performed.

Main Results:

The crystal structure features inversion-related cations forming dimers linked by N-H⋯S hydrogen bonds.
Iodide anions bridge adjacent cation dimers via N-H⋯I hydrogen bonds.
These interactions lead to the formation of zigzag chains propagating along the [001] direction, parallel to the bc plane.

Conclusions:

The crystal packing is dictated by a combination of cation dimerization and anion-cation hydrogen bonding.
The observed zigzag chain motif highlights the directional nature of hydrogen bonding in directing crystal architecture.
This structural characterization provides a foundation for further studies on the properties and potential applications of this class of organic salts.