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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.

Alkyl Halides

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Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
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Introduction
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Acid Halides to Amides: Aminolysis

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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...

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Related Experiment Video

Updated: Jun 1, 2026

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

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Published on: September 12, 2018

4-Meth-oxy-anilinium iodide.

¹Ordered Matter Science Research Center, College of Chemistry and Chemical, Engineering, Southeast UniVersity, Nanjing 210096, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|May 19, 2011

Summary

This summary is machine-generated.

The crystal structure of 4-methoxy-anilinium iodide was determined. This study reveals N-H⋯I hydrogen bonds and C-H⋯π contacts within the crystal lattice.

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Area of Science:

Crystallography
Solid-state chemistry
Supramolecular chemistry

Background:

Understanding the intermolecular interactions in organic salts is crucial for predicting their solid-state properties.
Anilinium derivatives are widely studied for their potential applications in materials science.

Purpose of the Study:

To elucidate the crystal structure of 4-methoxy-anilinium iodide.
To identify and characterize the non-covalent interactions governing the crystal packing.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the three-dimensional arrangement of atoms.
Analysis of the crystal structure to identify hydrogen bonds and other weak interactions.

Main Results:

The crystal structure of 4-methoxy-anilinium iodide (C(7)H(10)NO(+)·I(-)) was successfully determined.
Strong N-H⋯I hydrogen bonds were observed between the 4-methoxy-anilinium cations and iodide anions.
Weaker C-H⋯π contacts were also identified, contributing to the overall crystal packing.

Conclusions:

The crystal structure is stabilized by a combination of directional N-H⋯I hydrogen bonds and weaker C-H⋯π interactions.
These findings provide insights into the supramolecular assembly of anilinium salts and can inform the design of new materials.