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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.

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Related Experiment Video

Updated: Jun 8, 2026

A Technique to Functionalize and Self-assemble Macroscopic Nanoparticle-ligand Monolayer Films onto Template-free Substrates

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Published on: May 9, 2014

Controlling surface functionality through generation of thiol groups in a self-assembled monolayer.

Simon Q Lud¹, Stefan Neppl, Gerhard Richter

¹Walter Schottky Institut, Technische Universität München, 85747 Garching, Germany.

Langmuir : the ACS Journal of Surfaces and Colloids

|September 18, 2010

Summary

Researchers developed a new method to create reactive thiol groups on synthetic diamond surfaces. This functionalization enables controlled hybridization for biosensors and molecular electronics, facilitating protein grafting and electron transfer.

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Last Updated: Jun 8, 2026

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Area of Science:

Materials Science
Surface Chemistry
Nanotechnology

Background:

Synthetic diamond, particularly ultrananocrystalline diamond (UNCD), offers unique properties for electronic and biosensing applications.
Controlled surface functionalization is crucial for developing advanced biosensors and molecular electronic devices.
Thiol groups are versatile for surface modification and biomolecule immobilization.

Purpose of the Study:

To develop a lithographic method for generating reactive thiol groups on functionalized synthetic diamond.
To demonstrate the utility of thiol-functionalized UNCD for surface hybridization and biomolecule grafting.
To investigate the potential of these modified diamond surfaces in biosensor and molecular electronic applications.

Main Methods:

Ultrananocrystalline diamond (UNCD) thin films were functionalized.
Phenylsulfonic acid (PSA) monolayers on UNCD surfaces were irradiated to generate thiol head groups.
X-ray photoelectron spectroscopy (XPS), near-edge X-ray absorption fine structure (NEXAFS), and fluorescence microscopy were used for characterization.

Main Results:

A selective method for generating reactive thiol surface groups on UNCD was successfully developed.
Controlled thiol-disulfide exchange surface hybridization processes were demonstrated.
Yeast cytochrome c was grafted to the thiol-modified diamond surface, and electron transfer between the protein and electrode was confirmed.

Conclusions:

The developed lithographic method effectively generates reactive thiol groups on synthetic diamond surfaces.
Thiol-functionalized UNCD is a promising platform for biosensor and molecular electronic applications.
The ability to graft proteins and facilitate electron transfer opens avenues for bioelectronic interfaces.