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Related Concept Videos

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

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.
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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

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...
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

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.
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

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...
Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.

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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
09:54

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

Published on: September 12, 2018

4-Iodo-benzohydrazide.

Rifat Ara Jamal, Uzma Ashiq, Muhammad Nadeem Arshad

    Acta Crystallographica. Section E, Structure Reports Online
    |May 18, 2011
    PubMed
    Summary
    This summary is machine-generated.

    The crystal structure of C(7)H(7)IN(2)O reveals a benzene ring with an inclined hydrazide group. Intermolecular hydrogen bonds stabilize the structure, forming six- and ten-membered rings.

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    Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
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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
    09:54

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

    Published on: September 12, 2018

    Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
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    Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
    04:38

    Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

    Published on: July 28, 2022

    Area of Science:

    • Crystallography
    • Chemical Structure Analysis

    Background:

    • Understanding molecular interactions is crucial in chemical structure determination.
    • Hydrogen bonding plays a significant role in stabilizing crystal lattices.

    Purpose of the Study:

    • To elucidate the three-dimensional crystal structure of the compound C(7)H(7)IN(2)O.
    • To analyze the hydrogen bonding network and ring formation within the crystal structure.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular structure.
    • Analysis of hydrogen bond distances and angles was performed.
    • Graph-set notation was used to describe the hydrogen bonded ring systems.

    Main Results:

    • The hydrazide group in C(7)H(7)IN(2)O is inclined at 13.3(3)° relative to the benzene ring.
    • Intermolecular N-H⋯N and N-H⋯O hydrogen bonds were identified.
    • Six- and ten-membered hydrogen bonded rings were formed, denoted by R(2)(2)(6) and R(2)(2)(10) graph-set notations.

    Conclusions:

    • The crystal structure of C(7)H(7)IN(2)O is stabilized by a network of intermolecular hydrogen bonds.
    • The specific arrangement of hydrogen bonds leads to the formation of characteristic ring structures, influencing the overall crystal packing.