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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

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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.
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Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
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sp3d and sp3d 2 Hybridization
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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.
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N-Sulfur[n]arene: Synthesis and Solution-State Double-Threaded Dimerization Assisted by Multiple S···S Interactions.

Keiichiro Murakami1, Shunsuke Ohtani1, Kenichi Kato1

  • 1Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.

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This study shows macrocycle dimerization in solution via cooperative σ-hole and S···S interactions. These noncovalent forces enable the formation of stable, double-threaded dimers, overcoming solution-phase suppression challenges.

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Area of Science:

  • Supramolecular Chemistry
  • Chemical Crystallography
  • Solution-State Chemistry

Background:

  • Noncovalent interactions, such as σ-hole interactions, are crucial for building discrete supramolecular assemblies.
  • These interactions are often weakened or suppressed in solution, limiting their application in dynamic systems.
  • Developing methods to harness these interactions in solution is key for designing novel molecular architectures.

Purpose of the Study:

  • To demonstrate the solution-phase dimerization of a macrocycle driven by cooperative σ-hole interactions.
  • To investigate the structural and dynamic aspects of dimer formation in solution.
  • To explore the role of S···S contacts and alkyl-chain threading in stabilizing the dimer.

Main Methods:

  • Single-crystal X-ray diffraction to determine the solid-state structure of the dimer.
  • Concentration-dependent Nuclear Magnetic Resonance (NMR) spectroscopy to study dimerization in solution.
  • Diffusion-Ordered Spectroscopy (DOSY) to assess molecular size and aggregation in solution.

Main Results:

  • A double-threaded dimer structure was confirmed in the solid state, stabilized by alkyl-chain penetration and S···S contacts.
  • Evidence for dimer formation in solution was observed through concentration-dependent NMR.
  • DOSY experiments supported the presence of a stable dimer in solution, indicating cooperative stabilization.

Conclusions:

  • Cooperative σ-hole and S···S interactions can effectively drive macrocycle dimerization in solution.
  • Alkyl-chain threading and S···S contacts play a crucial role in stabilizing the supramolecular dimer in the solution phase.
  • This work highlights a strategy for utilizing weak noncovalent interactions to control self-assembly in solution.