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Related Concept Videos

Electrophiles02:28

Electrophiles

This lesson explains the definition, classification, and characteristic features of an electrophile that are key features of nucleophilic substitution reactions. An analysis of their charge and orbital picture helps understand their reactivity for seeking electrons. Electrophiles can be classified into positive and neutral species. Other classes include free radicals and polar functional groups.
While a positive electrophile, like a proton, reacts due to its vacant, low-energy 1s orbital, the...
Structure and Nomenclature of Thiols and Sulfides02:17

Structure and Nomenclature of Thiols and Sulfides

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, similar...
Preparation and Reactions of Thiols02:33

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.
Preparation and Reactions of Sulfides02:26

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.
Extraction: Advanced Methods00:56

Extraction: Advanced Methods

Metal ions can be separated from one another by complexation with organic ligands–the chelating agent– to form uncharged chelates. Here, the chelating agent must contain hydrophobic groups and behave as a weak acid, losing a proton to bind with the metal. Since most organic ligands used in this process are insoluble or undergo oxidation in the aqueous phase, the chelating agent is initially added to the organic phase and extracted into the aqueous phase. The metal-ligand complex is formed in...
Sulfur Assimilation01:20

Sulfur Assimilation

Sulfur is an essential element in biological systems, contributing to synthesizing key biomolecules, including amino acids such as cysteine and methionine, and cofactors such as coenzyme A and biotin. Microorganisms primarily assimilate sulfur as sulfate (SO₄²⁻) from the environment, which must undergo a series of biochemical transformations before it can be incorporated into cellular components. As sulfate is highly oxidized, it must undergo assimilatory sulfate reduction to become...

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Supercritical Nitrogen Processing for the Purification of Reactive Porous Materials
09:05

Supercritical Nitrogen Processing for the Purification of Reactive Porous Materials

Published on: May 15, 2015

Hydropersulfides: H-Atom Transfer Agents Par Excellence.

Jean-Philippe R Chauvin1, Markus Griesser1, Derek A Pratt1

  • 1Department of Chemistry and Biomolecular Sciences, University of Ottawa , Ottawa, Ontario K1N 6N5, Canada.

Journal of the American Chemical Society
|April 19, 2017
PubMed
Summary

Hydropersulfides (RSSH) are potent hydrogen atom donors, significantly outperforming thiols in radical scavenging due to their thermodynamic properties. Their reactivity rivals alpha-tocopherol, offering unique advantages in antioxidant defense, especially in specific environments.

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Synthesis of Metal Nanoparticles Supported on Carbon Nanotube with Doped Co and N Atoms and its Catalytic Applications in Hydrogen Production

Published on: December 6, 2021

Area of Science:

  • Biochemistry
  • Chemical Biology
  • Oxidative Stress Research

Background:

  • Hydropersulfides (RSSH) are endogenous compounds derived from hydrogen sulfide (H₂S).
  • RSSH are known to store H₂S in vivo and act as antioxidants.
  • Compared to thiols, RSSH exhibit higher reactivity towards two-electron oxidants.

Purpose of the Study:

  • To investigate the hydrogen (H)-atom transfer chemistry of hydropersulfides (RSSH).
  • To contrast the H-atom transfer capabilities of RSSH with those of thiols.
  • To evaluate the potential of RSSH as radical-trapping antioxidants.

Main Methods:

  • Kinetic studies of H-atom transfer reactions.
  • Thermodynamic analysis of RSSH bond dissociation enthalpies.
  • Comparison of RSSH reactivity with thiols and alpha-tocopherol (α-TOH).
  • Assessment of perthiyl radical stability and reactivity.

Main Results:

  • RSSH are potent H-atom donors to various radicals (alkyl, alkoxyl, peroxyl, thiyl), exceeding thiol reactivity by 1-4 orders of magnitude.
  • The high reactivity is attributed to a weak RSS-H bond (∼70 kcal/mol) and stable perthiyl radicals.
  • RSSH reactivity towards peroxyl radicals matches α-TOH, enhanced by secondary orbital interactions.
  • RSSH outperform α-TOH in H-bond-accepting media due to low H-bond acidity.
  • Resulting perthiyl radicals are persistent and rapidly dimerize, avoiding side reactions.

Conclusions:

  • RSSH possess exceptional H-atom donating ability, making them superior radical scavengers compared to thiols.
  • RSSH represent a versatile class of antioxidants with unique properties, particularly in non-polar or H-bond-accepting environments.
  • The stability and dimerization of perthiyl radicals contribute to the overall antioxidant efficacy of RSSH systems.