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Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

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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,...
2.1K
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...
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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
Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

8.7K
According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).
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Related Experiment Video

Updated: May 23, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

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Dicationic dibenzo[1,4]azaborine with an open-shell electronic structure.

Peiyuan Yang1, Yizhou Chen2, Takuma Kuroda3

  • 1Department of Quantum Beam Science, Graduate School of Science and Engineering, Ibaraki University, 4-12-1 Naka-narusawa, Hitachi, Ibaraki 316-8511, Japan.

Chemical Communications (Cambridge, England)
|May 2, 2025
PubMed
Summary
This summary is machine-generated.

A novel dibenzoazaborine dication was synthesized, existing as a hybrid of open-shell and closed-shell states. This unique molecule displays significant antiaromaticity within its azaborine ring.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Spectroscopy

Background:

  • Dibenzoazaborine compounds are of interest due to their unique electronic properties.
  • Understanding the electronic structure of dications is crucial for developing new materials.

Purpose of the Study:

  • To synthesize and characterize a novel dibenzoazaborine dication.
  • To investigate the electronic structure and aromaticity of the synthesized dication.

Main Methods:

  • Synthesis of the dibenzoazaborine dication (Dpa2DBAB2+).
  • Characterization using electron spin resonance (ESR) spectroscopy.
  • Computational analysis via density functional theory (DFT) calculations.

Main Results:

  • The dibenzoazaborine dication (Dpa2DBAB2+) was successfully synthesized and characterized.
  • The dication exists as a resonance hybrid of open-shell singlet (OS) and quinoidal closed-shell states (CS).
  • The azaborine ring within the dication demonstrated significant antiaromatic character.

Conclusions:

  • The study presents the first synthesis and characterization of a dibenzoazaborine dication.
  • The electronic structure is a unique resonance hybrid, challenging traditional aromaticity concepts.
  • The observed antiaromaticity in the azaborine ring opens new avenues for exploring electronic properties in boron-containing heterocycles.