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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

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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Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

2.3K
The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
2.3K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.7K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
2.7K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

1.8K
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...
1.8K
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

2.9K
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...
2.9K
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

4.0K
Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
4.0K

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Related Experiment Video

Updated: Jun 3, 2025

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
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Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography

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3-Iodo-aniline.

Ferhan Slamang1, Eric Cyriel Hosten1, Richard Betz1

  • 1Nelson Mandela University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa.

Iucrdata
|January 8, 2025
PubMed
Summary

This study details the crystal structure of meta-iodoaniline, revealing molecular chains formed by hydrogen bonds and sheets created by iodine interactions. This provides insights into organic crystal packing and intermolecular forces.

Area of Science:

  • Crystallography
  • Organic Chemistry
  • Materials Science

Background:

  • Aniline derivatives are important in various chemical applications.
  • Understanding crystal structures informs material properties.
  • Meta-iodoaniline (C6H6IN) is a specific derivative with potential applications.

Purpose of the Study:

  • To determine the crystal structure of meta-iodoaniline.
  • To elucidate the intermolecular interactions governing its solid-state arrangement.
  • To provide a foundation for understanding its physical and chemical properties.

Main Methods:

  • Single-crystal X-ray diffraction was employed to analyze the compound.
  • The crystal structure was solved and refined.
  • The asymmetric unit and twinning were characterized.
Keywords:
crystal structure

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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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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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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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Main Results:

  • The asymmetric unit contains two molecules of meta-iodoaniline.
  • The structure was refined as a two-component inversion twin (55.6:44.4 ratio).
  • Infinite N-H⋯N hydrogen-bonded chains along the a-axis and I⋯I contacts forming sheets perpendicular to the c-axis were observed.

Conclusions:

  • The crystal packing of meta-iodoaniline is dominated by N-H⋯N hydrogen bonds and I⋯I dispersive interactions.
  • These interactions lead to a layered structure with potential implications for solid-state reactivity and material design.
  • The detailed structural analysis contributes to the broader understanding of halogenated aniline derivatives.