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Related Concept Videos

Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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 para position.
Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
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...
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.
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.
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.

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Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

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2,6-Diazido-toluene.

Thomas M Klapötke1, Burkhard Krumm, Matthias Scherr

  • 1Department of Chemistry and Biochemistry, Ludwig-Maximilian University, Butenandtstrasse 5-13, D-81377 Munich, Germany.

Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
PubMed
Summary
This summary is machine-generated.

This study details the molecular structure of C(7)H(6)N(6), revealing nearly planar molecules and disordered methyl group hydrogen atoms. The azide groups exhibit standard geometry for covalently bonded azides.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Molecular Structure

Background:

  • Understanding the precise molecular arrangement of organic compounds is crucial for predicting their chemical behavior and potential applications.
  • C(7)H(6)N(6) is a compound with potential relevance in various chemical synthesis pathways.

Purpose of the Study:

  • To elucidate the detailed three-dimensional structure of the title compound, C(7)H(6)N(6).
  • To characterize bond distances, molecular planarity, and the positional disorder of hydrogen atoms within the methyl group.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular structure.
  • Analysis of bond lengths, angles, and atomic coordinates provided structural insights.

Main Results:

  • The compound C(7)H(6)N(6) was found to possess an almost planar molecular geometry.
  • Specific C-N bond distances were measured as 1.429(2) and 1.428(2) Å.
  • Hydrogen atoms of the methyl group exhibited disorder, distributed over two sites with occupancy factors of 0.69 and 0.31.
  • The azide groups displayed geometries consistent with covalently bonded azides.

Conclusions:

  • The determined crystal structure provides a fundamental understanding of C(7)H(6)N(6)'s molecular architecture.
  • The observed planarity, bond lengths, and hydrogen disorder offer valuable data for computational modeling and further chemical investigations.