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

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 –H

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.

Preparation and Reactions of Sulfides

Preparation and Reactions of Sulfides

Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic S_N1

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...

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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.

Preparation and Reactions of Thiols

Preparation and Reactions of Thiols

Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.

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Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

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From thia- to selenadiazoles: changing interaction priority.

Benjamin D Lindner¹, Benjamin A Coombs, Manuel Schaffroth

¹Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, 69120 Heidelberg, Germany.

Organic Letters

|January 17, 2013

Summary

Researchers synthesized novel alkynylated benzannulated selenadiazoles and compared them to thiadiazoles. Selenadiazoles exhibit unique dimerization driven by Se-N interactions, crucial for self-assembly and charge transport in thin-film devices.

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Utilizing Thermal Shift Assay to Probe Substrate Binding to Selenoprotein O

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Area of Science:

Organic Chemistry
Materials Science
Solid-State Chemistry

Background:

Alkynylated benzannulated heterocycles are of interest for electronic applications.
Understanding structure-property relationships is key for designing new materials.

Purpose of the Study:

To synthesize and characterize novel alkynylated benzannulated selenadiazoles.
To compare their properties and solid-state structures with analogous thiadiazoles.
To investigate the role of Se-N interactions in self-assembly and charge transport.

Main Methods:

Synthesis of selenadiazole and thiadiazole derivatives.
Optical and electrochemical property measurements.
Single-crystal X-ray diffraction analysis.

Main Results:

Successful synthesis of a series of alkynylated benzannulated selenadiazoles.
Selenadiazoles exhibit head-to-head dimerization in the solid state.
Thiadiazole packing is influenced by steric effects of side groups.
Se-N interactions identified as a key supramolecular motif.

Conclusions:

Alkynylated benzannulated selenadiazoles possess distinct solid-state structures compared to thiadiazoles.
Se-N interactions facilitate self-assembly and can modulate charge transport in thin films.
These findings provide insights for designing organic electronic materials.