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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.

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 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.

Metal-Ligand Bonds

Metal-Ligand Bonds

The hemoglobin in the blood, the chlorophyll in green plants, vitamin B-12, and the catalyst used in the manufacture of polyethylene all contain coordination compounds. Ions of the metals, especially the transition metals, are likely to form complexes.
In these complexes, transition metals form coordinate covalent bonds, a kind of Lewis acid-base interaction in which both of the electrons in the bond are contributed by a donor (Lewis base) to an electron acceptor (Lewis acid). The Lewis acid in...

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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Updated: Jun 28, 2026

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

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Silyl-substituted thioether ligands and their Ag(I) complexes.

Chinwon Rim¹, Hongming Zhang, David Y Son

¹Department of Chemistry, P.O. Box 750314, Southern Methodist University, Dallas, Texas 75275-0314, USA.

Inorganic Chemistry

|November 15, 2008

Summary

New silyl-substituted thioether ligands were synthesized and reacted with silver(I) triflate. The resulting silver complexes exhibited diverse structures, including polymeric forms, with common argentophilic interactions observed in solid-state analyses.

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Last Updated: Jun 28, 2026

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Published on: April 9, 2018

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Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents

Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents

Published on: May 28, 2014

Area of Science:

Organometallic Chemistry
Coordination Chemistry
Materials Science

Background:

Thioether ligands are versatile in coordination chemistry.
Silyl-substituted organic molecules offer unique electronic and steric properties.
Silver(I) complexes are of interest for their structural diversity and potential applications.

Purpose of the Study:

To synthesize novel silyl-substituted thioether ligands.
To investigate the coordination behavior of these ligands with silver(I).
To characterize the solid-state structures of the resulting silver complexes.

Main Methods:

Ligand synthesis via deprotonation of thioethers with n-butyllithium and subsequent reaction with chlorosilanes.
Complexation with silver(I) triflate.
Characterization using single-crystal X-ray crystallography.

Main Results:

Silyl-substituted thioether ligands were successfully prepared in 45-75% yields.
The majority of ligands formed stable, crystalline silver(I) complexes in high yields.
X-ray crystallography revealed diverse structures, from discrete units to infinite polymers.
Argentophilic interactions (Ag-Ag distances of 2.909-3.196 Å) were frequently observed.

Conclusions:

Silyl-substitution provides a tunable platform for designing thioether ligands.
Silver(I) complexes with these ligands display rich structural polymorphism.
The observed argentophilic interactions are a significant structural feature in these silver complexes.