Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

Preparation and Reactions of Thiols

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 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.

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, similar...

SN2 Reaction: Mechanism

S_N2 Reaction: Mechanism

The kinetic studies of SN2 reactions suggest an essential feature of its mechanism: it is a single-step process without intermediates. Here, both the nucleophile and the substrate participate in the rate-determining step.
The presence of the more electronegative halogen in the substrate creates a polarized carbon-halide bond. The halide pulls the electron cloud generating an electrophilic center at the carbon atom. Thus, the carbon atom carries a partial positive charge while the halide has a...

Nitrosation of Enols

Nitrosation of Enols

The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.

SN1 Reaction: Mechanism

S_N1 Reaction: Mechanism

Kinetic studies of ionization of a tertiary halide in a protic solvent suggest that only the substrate participates in the rate-determining step (slow step). The nucleophile is involved only after the slowest step. The SN1 reaction takes place in a multiple-step mechanism.
Firstly, the haloalkane ionizes to generate a carbocation intermediate and a halide ion. This heterolytic cleavage is highly endothermic with large activation energy. The ionization of the substrate, facilitated by a polar...

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by

Same author

Direct Evidence for the Sulfonium-Mediated Photopolymerization of 1,2-Dithiolanes.

Journal of the American Chemical Society·2026

Same author

Tunable Mechanical Anisotropy, Crack Guiding, and Toughness Enhancement in Two-Stage Reactive Polymer Networks.

Advanced engineering materials·2026

Same author

Tailoring fully biobased optical adhesives <i>via</i> hydrogen-bonding modulation.

RSC applied polymers·2026

Same author

Ultrafast-relaxing and photopolymerizable PEG hydrogels enable viscoelasticity-mediated cell remodeling in synthetic matrices.

Matter·2026

Same author

Preparation of Degradable Polymers Containing Tunable Ratios of Dithioacetals and Disulfides via Mixed Mode Polymerization.

Angewandte Chemie (International ed. in English)·2025

Same author

Digital light processing of photoresponsive and programmable hydrogels.

Science advances·2025

Search research articles

Related Experiment Video

Updated: Jun 16, 2026

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation

Published on: August 1, 2018

Thiol-ene click chemistry.

Charles E Hoyle¹, Christopher N Bowman

¹School of Polymers and High Performance Materials, University of Southern Mississippi, Hattiesburg, MS 39406-0001, USA.

Angewandte Chemie (International Ed. in English)

|February 19, 2010

Summary

This summary is machine-generated.

The radical-mediated thiol-ene reaction is an efficient click reaction ideal for materials science. Photoinitiation enables precise control in polymerizations, offering high yields and uniform networks.

More Related Videos

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

Published on: August 19, 2012

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

Published on: April 9, 2018

Related Experiment Videos

Last Updated: Jun 16, 2026

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation

Published on: August 1, 2018

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

Published on: August 19, 2012

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

Published on: April 9, 2018

Area of Science:

Synthetic Chemistry
Materials Science
Polymer Chemistry

Background:

The concept of 'click reactions' has driven innovation in synthetic chemistry and materials science.
The radical-mediated thiol-ene reaction is recognized for its efficiency and desirable characteristics.

Purpose of the Study:

To review the radical-mediated thiol-ene reaction as a key click reaction.
To highlight its mechanism, applications, and advantages in various chemical processes.

Main Methods:

Literature review of radical-mediated thiol-ene reactions.
Analysis of photoinitiation mechanisms in polymerization.
Examination of applications in synthesis, biofunctionalization, and material modification.

Main Results:

The thiol-ene reaction exhibits high efficiency, simplicity, and rapid kinetics with no side products.
Photoinitiation allows for excellent spatial and temporal control, particularly in photopolymerizations.
The reaction yields highly uniform polymer networks with unique properties.

Conclusions:

The radical-mediated thiol-ene reaction is a versatile and powerful click chemistry tool.
Its photoinitiated nature provides advanced control for creating functional materials.
This reaction is crucial for advancements in polymer synthesis and surface modification.