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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,...

Sulfur Assimilation

Sulfur Assimilation

Sulfur is an essential element in biological systems, contributing to synthesizing key biomolecules, including amino acids such as cysteine and methionine, and cofactors such as coenzyme A and biotin. Microorganisms primarily assimilate sulfur as sulfate (SO₄²⁻) from the environment, which must undergo a series of biochemical transformations before it can be incorporated into cellular components. As sulfate is highly oxidized, it must undergo assimilatory sulfate reduction to...

Electrophilic Aromatic Substitution: Sulfonation of Benzene

Electrophilic Aromatic Substitution: Sulfonation of Benzene

Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.

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.

The Sulfur Cycle

The Sulfur Cycle

Sulfur, an important element in the chemical makeup of proteins, is recycled through the atmosphere and aquatic and terrestrial environments. Found in the atmosphere as sulfur dioxide (SO2), sulfur is released by decaying organisms, weathered rocks, geothermal vents, volcanos, and burning fossil fuels. It is deposited into the ecosystem, cycled through the biotic community, and either released back into the atmosphere as gas or deposited in marine sediment for long-term storage and eventual...

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Updated: Dec 21, 2025

Synthesis of Terpolymers at Mild Temperatures Using Dynamic Sulfur Bonds in PolyS-Divinylbenzene

Synthesis of Terpolymers at Mild Temperatures Using Dynamic Sulfur Bonds in PolyS-Divinylbenzene

Published on: May 20, 2019

Suit[4]ane.

Wenqi Liu¹, Charlotte L Stern¹, J Fraser Stoddart^1,2,3

¹Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States.

Journal of the American Chemical Society

|May 19, 2020

Summary

This summary is machine-generated.

Researchers created a novel porphyrin-based suit[4]ane using a molecular ship-in-a-bottle technique. This mechanically interlocked molecule features a porphyrin core encapsulated within a cyclophane via a slippage mechanism.

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Published on: April 9, 2018

Area of Science:

Supramolecular Chemistry
Mechanical Molecular Engineering

Background:

Mechanically interlocked molecules (MIMs) are complex architectures with unique properties.
The "ship-in-a-bottle" synthesis of MIMs, particularly suitanes, presents significant synthetic challenges.

Purpose of the Study:

To synthesize a novel porphyrin-based suit[4]ane.
To demonstrate the "slippage" mechanism for constructing this challenging molecular architecture.

Main Methods:

Synthesis of a porphyrin precursor with protruding ligands (limbs).
Encapsulation of the porphyrin within a tricyclic octacationic cyclophane via a temperature-controlled slippage mechanism.
Dynamic proton nuclear magnetic resonance (1H NMR) spectroscopy to study molecular motion.

Main Results:

Successful synthesis of a porphyrin-based suit[4]ane.
Demonstration of the slippage mechanism for facile porphyrin encapsulation.
Observation of rapid rocking motion of the encapsulated porphyrin within the cyclophane cavity.

Conclusions:

The study reports a new porphyrin-based suit[4]ane, advancing the field of mechanically interlocked molecules.
The slippage mechanism offers an efficient route for constructing complex molecular architectures.
The dynamic behavior of the encapsulated porphyrin highlights the unique properties of these systems.