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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.

Nitrosation of Enols

Nitrosation of Enols

The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.

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 of Nitriles

Preparation of Nitriles

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...

Electrophilic Aromatic Substitution: Nitration of Benzene

Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.

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One-pot thioether formation from S-nitrosothiols.

Dehui Zhang¹, Nelmi O Devarie-Baez, Jia Pan

¹Department of Chemistry, Washington State University, Pullman, Washington 99164, USA.

Organic Letters

|November 18, 2010

Summary

This summary is machine-generated.

Researchers developed a new one-pot reaction to stabilize unstable S-nitrosothiols, the products of protein S-nitrosation. This method improves the detection of protein S-nitrosation, a crucial post-translational modification.

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Area of Science:

Biochemistry
Molecular Biology
Chemical Biology

Background:

Protein S-nitrosation is a critical post-translational modification.
Detecting S-nitrosation is challenging due to the instability of S-nitrosothiol products.

Purpose of the Study:

To develop a novel reaction for stabilizing S-nitrosothiols.
To facilitate the detection of protein S-nitrosation.

Main Methods:

A new one-pot reaction was employed.
The reaction selectively converts S-nitrosothiols to stable thioethers.
The process occurs under mild conditions.

Main Results:

Unstable S-nitrosothiols were successfully converted to stable thioethers.
The conversion was achieved in a single reaction vessel (one-pot).
The reaction proceeded efficiently under mild experimental conditions.

Conclusions:

A new, mild, one-pot reaction effectively stabilizes S-nitrosothiols.
This method offers a promising approach for the reliable detection of protein S-nitrosation.