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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,...

Alcohols from Carbonyl Compounds: Reduction

Alcohols from Carbonyl Compounds: Reduction

Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...

Nucleophilic Addition to the Carbonyl Group: General Mechanism

Nucleophilic Addition to the Carbonyl Group: General Mechanism

The carbonyl carbon in an aldehyde or ketone is the site of a nucleophilic attack due to its electron-deficient nature. Depending on the strength of the incoming nucleophile, the reaction occurs via different mechanistic pathways.
A stronger nucleophile can directly attack the electrophilic center, the carbonyl carbon. The HOMO orbital of the nucleophile interacts with the LUMO (π* antibonding) orbital present on the carbonyl carbon. This interaction breaks the π bond and shifts the π...

IR Frequency Region: Alkene and Carbonyl Stretching

IR Frequency Region: Alkene and Carbonyl Stretching

Double bonds in alkenes and carbonyl compounds exhibit stretching frequencies in the diagnostic region of the IR spectrum. In addition, alkenes exhibit vinylic C–H stretching and C–H out-of-plane bending absorptions that are useful for identifying substitution patterns.
Stretching frequencies are affected by several factors, such as resonance, inductive effects, ring strain, dipole moment, and hydrogen bonding. Consequently, the stretching frequency of the carbonyl double bond...

Alcohols from Carbonyl Compounds: Grignard Reaction

Alcohols from Carbonyl Compounds: Grignard Reaction

Grignard reagents are one of the most commonly used reagents used to synthesize alcohols from carbonyl compounds. Grignard reagents are organomagnesium halides with a highly polar carbon–magnesium bond. Due to the partial ionic nature of the C–Mg bond, the carbon functions as a strong nucleophile and attacks electrophiles like carbonyl carbon.
Magnesium from the reagent coordinates with carbonyl oxygen, further reducing the carbonyl carbon's electron density. Thus, the...

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Iron Carbide-Sulfide Carbonyl Clusters.

Liang Liu¹, Thomas B Rauchfuss¹, Toby J Woods¹

¹School of Chemical Sciences , University of Illinois , Urbana , Illinois 61801 , United States.

Inorganic Chemistry

|June 12, 2019

Summary

Researchers synthesized novel iron carbide-sulfide clusters, including the first face-capped octahedral and edge-fused double clusters. These compounds offer potential as active-site analogues for key biological cofactors.

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Area of Science:

Inorganic Chemistry
Organometallic Chemistry
Materials Science

Background:

Iron-sulfur clusters are crucial in biological systems, particularly in nitrogen fixation.
Understanding the synthesis and properties of novel iron-sulfur compounds can provide insights into these biological processes.

Purpose of the Study:

To report the synthesis of the first iron carbide-sulfide clusters.
To explore the structural diversity and reactivity of these novel clusters.
To assess their potential as models for biological active sites.

Main Methods:

Synthesis of iron carbide-sulfide clusters starting from [Fe6C(CO)16]2-.
O-methylation and demethoxylation reactions to form sulfinite and sulfide clusters.
Characterization of cluster structures and redox properties.

Main Results:

Successful preparation of the first iron carbide-sulfides, including face-capped octahedral and edge-fused double clusters.
Characterization of sulfinite [Fe6C(CO)15(SO2)]2- and sulfide [Fe6C(CO)16(S)] clusters.
Investigation of the redox behavior and hydrolysis of the sulfide cluster.

Conclusions:

The synthetic routes provide access to the Fe6CSx cluster family.
These novel clusters may serve as valuable active-site analogues for FeMoco and FeVco cofactors.
Further studies can elucidate their role in mimicking biological functions.