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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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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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Structure and Nomenclature of Thiols and Sulfides02:17

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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,...
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sp3d and sp3d 2 Hybridization
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The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...
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Two NMR-active nuclei bonded to a central atom can be involved in geminal or two-bond coupling. Geminal coupling is commonly seen between diastereotopic protons in chiral molecules and unsymmetrical alkenes, among others.
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2,2'-Dithiobispyrazine: about the disulfide bond.

Kinga Wzgarda-Raj1, Justyna Dominikowska1, Natallia Husik1

  • 1Department of Physical Chemistry, University of Łódź, Pomorska 163/165, Łódź 91-236, Poland.

Acta Crystallographica. Section C, Structural Chemistry
|August 29, 2023
PubMed
Summary

Pyrazine-2-thiol oxidizes to form 2,2'-dithiobispyrazine, a disulfide compound. Quantum studies reveal its stable conformation and reactivity, indicating potential for SN2 reactions.

Keywords:
2,2′-dithiobispyrazineSN2 mechanismchalcogen bondcrystal structuredisulfide bondquantum-chemical calculations

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Area of Science:

  • Crystallography
  • Quantum Chemistry
  • Organic Chemistry

Background:

  • Pyrazine-2-thiol is a heterocyclic compound.
  • Disulfide compounds exhibit diverse molecular conformations.
  • Understanding molecular structure influences chemical reactivity.

Purpose of the Study:

  • To investigate the aerial oxidation product of pyrazine-2-thiol.
  • To determine the molecular structure and conformation of 2,2 '-dithiobispyrazine.
  • To explore the reactivity and stable rotamers of the disulfide.

Main Methods:

  • X-ray diffraction for structural analysis.
  • Cambridge Structural Database search for conformational comparison.
  • Quantum theoretical studies for rotamer analysis and reaction mechanism investigation.

Main Results:

  • Pyrazine-2-thiol condenses to form 2,2 '-dithiobispyrazine under aerial conditions.
  • The molecule exhibits an almost perpendicular arrangement of pyrazine rings with a C-S-S-C torsion angle of -91.45 °.
  • The lowest energy rotamer, observed in the crystalline state, is stabilized by various intermolecular interactions.
  • Quantum chemical computations confirm the potential for SN2 reactions.

Conclusions:

  • The study elucidates the structure and conformational preferences of 2,2 '-dithiobispyrazine.
  • The findings highlight the role of intermolecular interactions in stabilizing the observed crystal structure.
  • 2,2 '-dithiobispyrazine is predicted to undergo reactions via the SN2 mechanism.