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Updated: Jun 27, 2025
12:30
Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
Published on: April 9, 2018
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Geminal-dithiol-based precursors for reactive sulfur species.
Shi Xu1, Geat Ramush1, Iris J Yang1
1Department of Chemistry, Brown University, Providence, Rhode Island, 02912, USA. ming_xian@brown.edu.
Chemical Communications (Cambridge, England)
|May 7, 2024
Summary
Free gem-dithiols are explored as reactive sulfur species (RSS) donors. 1,3-diphenylpropane-2,2-dithiol releases H2S, acts as a NO donor, and facilitates sulfur transfer reactions.
Area of Science:
- Chemistry
- Biochemistry
- Chemical Biology
Background:
- Caged gem-dithiols are established reactive sulfur species (RSS) donors.
- The chemical behavior of free gem-dithiols as RSS precursors remains largely unexplored.
Purpose of the Study:
- To investigate the potential of free gem-dithiols as versatile precursors for various reactive sulfur species.
- To characterize the reactivity of 1,3-diphenylpropane-2,2-dithiol in releasing different sulfur-containing molecules.
Main Methods:
- Synthesis and characterization of 1,3-diphenylpropane-2,2-dithiol.
- Investigation of its decomposition under physiological conditions.
- Chemical conversion to a mono-S-nitrosothiol and a dithiirane derivative.
Main Results:
- 1,3-diphenylpropane-2,2-dithiol releases hydrogen sulfide (H2S) under physiological conditions.
- It can be transformed into a mono-S-nitrosothiol, functioning as a nitric oxide (NO) donor.
- Conversion to 3,3-dibenzyldithiirane yields an active sulfur transfer reagent capable of inducing S-persulfidation.
Conclusions:
- Free gem-dithiols represent a promising class of precursors for generating diverse reactive sulfur species.
- 1,3-diphenylpropane-2,2-dithiol demonstrates multifaceted reactivity, serving as a source for H2S, NO, and facilitating sulfur transfer.
- This study expands the understanding of gem-dithiol chemistry and its applications in biological and chemical contexts.
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