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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.

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

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Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...

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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.

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Updated: Jan 4, 2026

Combining Solid-state and Solution-based Techniques: Synthesis and Reactivity of ChalcogenidoplumbatesII or IV

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Published on: December 29, 2016

A new polymorph of phenylselenium trichloride.

Hannah R Bloomfield¹, Jamie S Ritch¹

¹Department of Chemistry, The University of Winnipeg, 515 Portage Avenue, Winnipeg, MB, R3B 2E9, Canada.

Acta Crystallographica. Section C, Structural Chemistry

|November 6, 2019

Summary

A new polymorph of phenylselenium trichloride was discovered, featuring noncovalent dimer units instead of polymer chains. This finding advances understanding of organoselenium trihalide structures.

Keywords:

chalcogen–halogen interaction crystal structure phenylselenium trichloride polymorph selenium compound

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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

Published on: November 22, 2016

Area of Science:

Organometallic Chemistry
Solid-State Chemistry
Crystallography

Background:

Phenylselenium trichloride (PhSeCl3) is an organoselenium compound with known structural characteristics.
Understanding polymorphism is crucial for predicting and controlling material properties.

Purpose of the Study:

To disclose and characterize a second polymorph of phenylselenium trichloride.
To investigate the structural differences and bonding interactions in the new polymorph.

Main Methods:

Single-crystal X-ray diffraction was used to determine the molecular and crystal structure.
Density functional theory (DFT) calculations were employed to study energetics and isomer stability.

Main Results:

A novel polymorph of PhSeCl3 was identified, consisting of asymmetric chlorine-bridged noncovalent dimer units.
These dimers exhibit weak Se...Cl interactions, linking adjacent dimers.
DFT calculations indicated the anti isomer is energetically close to the observed syn form.

Conclusions:

This discovery represents the first additional polymorph reported for an organoselenium trihalide.
The findings provide new insights into the structural diversity and noncovalent interactions in organoselenium compounds.