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Preparation and Reactions of Sulfides

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.

Preparation and Reactions of Thiols

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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.

Structure and Nomenclature of Thiols and Sulfides

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,...

Redox Titration: Other Oxidizing and Reducing Agents

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Besides iodine, other oxidizing or reducing agents can serve as titrants in redox titrations. Common oxidizing titrants include KMnO4, cerium(IV), and K2Cr2O7. The choice of oxidizing titrants depends on factors like stability, cost, analyte strength, and reaction rate between the analyte and titrant. KMnO4 is a strong oxidizing titrant that reduces from Mn(VII) to Mn(II) in a highly acidic solution, simultaneously oxidizing the analyte to a higher oxidation state. In this case, KMnO4 acts as a...

Electrophilic Aromatic Substitution: Sulfonation of Benzene

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Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.

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Updated: Jul 20, 2025

Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates

Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates

Published on: March 6, 2019

Serinol-Based Versatile Disulfide-Reducing Reagent.

Babita Kushwaha¹, Sinenhlanhla N Mthembu^1,2, Anamika Sharma^1,2,3

¹KwaZulu-Natal Research Innovation and Sequencing Platform (KRISP), School of Laboratory Medicine and Medical Sciences, College of Health Sciences, University of KwaZulu-Natal, Durban 4041, South Africa.

Molecules (Basel, Switzerland)

|July 29, 2023

Summary

This summary is machine-generated.

Researchers synthesized two new disulfide-reducing agents, DPDT and DMPDT. DPDT demonstrated superior stability and comparable reducing capacity to DTT, showing promise for various applications.

Keywords:

cysteine disulfide-reducing agents dithiols monothiols phosphines

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A Facile and Efficient Approach for the Production of Reversible Disulfide Cross-linked Micelles

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A Facile and Efficient Approach for the Production of Reversible Disulfide Cross-linked Micelles

A Facile and Efficient Approach for the Production of Reversible Disulfide Cross-linked Micelles

Published on: December 23, 2016

Area of Science:

Chemical Synthesis
Biochemistry
Organic Chemistry

Background:

Disulfide bonds are crucial in protein structure and function.
Effective reducing agents are needed for various biochemical and chemical processes.
Existing reducing agents like DTT have limitations.

Purpose of the Study:

To synthesize novel disulfide-reducing agents.
To evaluate the stability and efficacy of the synthesized compounds.
To compare the performance of the most stable agent with established reducing agents.

Main Methods:

Synthesis of 2-(dibenzylamino) propane-1,3-dithiol (DPDT) from serinol.
Synthesis of 2-(dibenzylamino)-2-methylpropane-1,3-dithiol (DMPDT) from methyl serinol.
Stability assessment of DPDT and DMPDT.
Evaluation of DPDT's reducing capacity in liquid and solid phases.

Main Results:

DPDT and DMPDT were successfully synthesized.
DPDT exhibited greater stability compared to DMPDT.
DPDT demonstrated comparable reducing capacity to Dithiothreitol (DTT).
DPDT showed effectiveness in both liquid and solid-phase applications.

Conclusions:

DPDT is a stable and effective disulfide-reducing agent.
DPDT presents a viable alternative to DTT in various applications.
The synthesized dithiol compounds hold potential for biochemical research and chemical synthesis.