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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

4.8K
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.
4.8K
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

4.1K
The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is...
4.1K
Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

6.2K
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.
6.2K
Structure and Nomenclature of Thiols and Sulfides02:17

Structure and Nomenclature of Thiols and Sulfides

4.7K
Thiols and sulfides are sulfur analogs of alcohols and ethers, respectively, where the sulfur atom takes the place of the oxygen atom. Thus, thiols are generally represented as RSH, where R is an alkyl substituent and —SH is the functional group. On the other hand, in sulfides, the central sulfur atom is bonded to two hydrocarbon groups on either side. Depending upon the type of group, sulfides can be either symmetrical or asymmetrical. Both thiols and sulfides display a bent geometry,...
4.7K
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
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

10.2K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
10.2K

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N,N'-Diaryl-Sulfurdiimides are Strongly Redox Tuned.

Nathan D D Hill1, René T Boeré1

  • 1Department of Chemistry and Biochemistry and The Canadian Centre for Research in Advanced Fluorine Technologies, University of Lethbridge, 4401 University Dr. W, Lethbridge, AB, Canada, T1K3M4.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|March 5, 2024
PubMed
Summary

This study details nine aryl sulfur diimides (SDIs), revealing their tunable electrochemical properties. Substituent effects strongly influence reduction potentials, correlating with computed orbital energies, offering new insights into thiazyl chemistry.

Keywords:
DFT computationEPR spectroelectrochemistrySC-XRD structure determinationUV-vis spectroscopychemical synthesiselectrochemistryinfrared spectroscopythiazyl chemistry

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Area of Science:

  • Inorganic Chemistry
  • Materials Science
  • Computational Chemistry

Background:

  • Sulfur diimides (SDIs) are a class of thiazyl compounds with unique properties.
  • Understanding their fundamental characteristics is crucial for developing new materials and chemical processes.

Purpose of the Study:

  • To synthesize and characterize nine aryl sulfur diimides (SDIs).
  • To investigate the electrochemical behavior and substituent effects on reduction potentials.
  • To clarify physical properties and solution-state conformations of SDIs.

Main Methods:

  • Synthesis and extensive experimental characterization of nine SDIs.
  • Computational modeling to investigate fundamental properties.
  • Electrochemical analysis, including reduction potential measurements.
  • Electron paramagnetic resonance (EPR) spectroscopy.
  • Infrared (IR) spectroscopy and X-ray crystallography.

Main Results:

  • Demonstrated a strong, quantifiable correlation between substituent properties and SDI reduction potentials.
  • Established a close link between electrochemical response and computed orbital energies.
  • Determined the nature, localization, and lifetimes of SDI radical anions using EPR.
  • Corrected historical assignments of IR spectroscopic data and resolved long-standing questions about solution-state conformations.
  • Showcased the utility of NoSpherA2 software for accurate crystal structure refinement.

Conclusions:

  • The electrochemical behavior of SDIs is highly tunable by substituents.
  • Computational and experimental data provide a clear understanding of SDI properties.
  • This work resolves key ambiguities regarding SDI structure and spectroscopy.