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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.

Formation of Complex Ions

Formation of Complex Ions

A type of Lewis acid-base chemistry involves the formation of a complex ion (or a coordination complex) comprising a central atom, typically a transition metal cation, surrounded by ions or molecules called ligands. These ligands can be neutral molecules like H2O or NH3, or ions such as CN− or OH−. Often, the ligands act as Lewis bases, donating a pair of electrons to the central atom. These types of Lewis acid-base reactions are examples of a broad subdiscipline called coordination...

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...

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.

Complexation Equilibria: The Chelate Effect

Complexation Equilibria: The Chelate Effect

In complexation reactions, metal atoms or cations interact with ligands to form donor-acceptor adducts called metal complexes. Ligands that bind through one donor site are monodentate, ligands with two donor sites are bidentate, and those with more than two donor sites are polydentate ligands. For example, ethylene diamine is a bidentate ligand that binds through two nitrogen donor atoms, forming a five-membered ring. EDTA is a polydentate ligand that binds through four oxygen and two nitrogen...

Complexation Equilibria: Factors Influencing Stability of Complexes

Complexation Equilibria: Factors Influencing Stability of Complexes

In complexation reactions, metal cations are the electron pair acceptors, and the ligands are the electron pair donors. The stability of the metal complexes depends primarily on the complexing ability of the central metal ion and the nature of the ligands. Generally, the complexing ability of the metal ion depends on the size and charge of the ion. As the metal ion size increases, the stability of the metal complexes decreases, provided that the valency of the metal ion and the ligands remain...

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Related Experiment Video

Updated: Jun 3, 2026

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

The first homoleptic gold(I) thiosulfonate complex.

Adam J Fischmann¹, Leone Spiccia

¹School of Chemistry, Monash University, Victoria, 3800, Australia.

Dalton Transactions (Cambridge, England : 2003)

|April 2, 2011

Summary

Researchers synthesized a novel gold(I) thiosulfonate complex. This complex forms unique anionic dimers with aurophilic interactions, showing distinct structural properties compared to gold thiosulfate compounds.

Area of Science:

Inorganic Chemistry
Coordination Chemistry
Materials Science

Background:

Gold(I) complexes are of interest due to their unique electronic and structural properties.
Aurophilic interactions play a significant role in the self-assembly and properties of gold compounds.
Thiosulfonate ligands offer a novel coordination environment for metal ions.

Purpose of the Study:

To synthesize and characterize a new gold(I) thiosulfonate complex.
To investigate the structural features, including coordination geometry and intermolecular interactions.
To compare the structural parameters with related gold thiosulfate complexes.

Main Methods:

Synthesis of the tetraethylammonium gold(I) thiosulfonate complex, Et(4)N[Au(MeS(2)O(2))(2)].

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Combining Solid-state and Solution-based Techniques: Synthesis and Reactivity of Chalcogenidoplumbates(II or IV)

Combining Solid-state and Solution-based Techniques: Synthesis and Reactivity of Chalcogenidoplumbates(II or IV)

Published on: December 29, 2016

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Last Updated: Jun 3, 2026

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

Synthesis and Characterization of Amphiphilic Gold Nanoparticles

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Combining Solid-state and Solution-based Techniques: Synthesis and Reactivity of Chalcogenidoplumbates(II or IV)

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X-ray crystallography to determine the solid-state structure.

Analysis of gold-gold distances and dihedral angles.

Main Results:

A linear coordination geometry around the gold(I) ion by terminal sulfur atoms of two thiosulfonate ligands was observed.
Discrete anionic dimers, [Au(MeS(2)O(2))(2)](2)(2-), were formed through aurophilic interactions.
The Au···Au distance and dihedral angle in the thiosulfonate dimer were found to be shorter and smaller, respectively, than in the thiosulfate analogue.

Conclusions:

The study reports a novel gold(I) thiosulfonate complex with unique structural characteristics.
Aurophilic interactions in this complex lead to the formation of anionic dimers with specific geometric parameters.
The findings provide insights into the influence of thiosulfonate ligands on gold coordination chemistry.