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When we talk about sulphide organic compounds, we automatically picture a couple of organic groups that are linked to a single sulphur molecule. The organic sulphides are represented by the formula RSR’ which is analogous to the ethers that consist of a central oxygen atom (ROR’). The R and R’ in organic sulphides signify an aryl group or an alkyl organic group. At times they can point out to both the groups at the same time. Cyclic sulphides are a class of sulphide organic compounds that depict multiple sulphur atoms in different areas of a single chain of carbon. The phase ‘thio’ is used before an organic sulphide where some different functional groups get priority over alkyl and aryl groups. The organic sulphur found in these complexes shows poor solubility in water, on the other hand, they are profound organic solvents. The organic sulphides with less amount of molar mass tend to give off a toxic smell. Acyclic organic sulphides incorporate methionine which is an essential amino acid. Methionine is naturally found in processes like methyl transfer. Crude petroleum contains sulphide organic compounds as functional groups like sulphides and thiols. These are generated when sulphur interacts with hydrocarbons due to the action of microbes that affect the sulfate deposits in mineral-rich rocks. With maturation, these organic compounds mature into more stable benzothiophene. Hydrogen sulphide is an inorganic sulphide that we receive as an end product when we treat crude petroleum with molybdenum. This is done to eliminate the foul smell of organic sulphide. Another major source of organic sulphide is traced in herbicides.
Structure of organic sulphides
Organic sulphides are identified as naturally occurring functional groups that are characterized by 90 degrees angles between the C – S links. It has a prototype which we refer to as the dimethyl sulphide. The C – S – C bonds in dimethyl sulphide form a bond angle of 99 degrees. The volatile samples of sulphides resemble thiols as both the organic molecules give off a strong smell. The physical aspects of sulphide organic compounds are identical to that of ethers. Though they are known for poor wetting properties, organic sulphides have a higher melting point when compared to ethers.
Now let us understand the concept of thiophenes. These are heterocyclic complexes. Therefore we come across two different substances as monomers in the structural ring. Thiophenes represent a category of organic sulphides that stand out due to their aromatic nature. Though thiophenes are non-nucleophilic, a few properties of these complexes resemble that of sulphides. Hydrogenation of thiophenes produces an organic complex called tetrahydrothiophene (C4H8S). This final product itself incorporates organic sulphides.
The general structural formation of organic sulphides is given as R1 – S – R2
Production of sulphides
Thiols are treated with the chemical procedures of alkylation to form sulphides. These critical procedures generally occur in addition to a basic matter. This assists in converting the functional thiol groups into a greater nucleophilic alternative which we term thiolate.
R – Br + H – R → HBr + R – S – R’
Similarly, reactions are very popular and they are initiated with the introduction of Grignard reagents.
Thiols are made to react with alkenes in a chemical reaction which is tagged in organic chemistry as the thiol-ene process. These chemical interactions are boosted with the use of catalysts that are derived from photoinitiators. These catalyzing agents are present in the form of free radicals.
There is another famous manufacturing process of sulphides which we refer to as the Pummerer rearrangement.
Nu– + R3S+ → R – S – R + Nu – R
Chemists exploit this chemical reaction in biological systems to transfer alkyl functional groups. A popular example can be cited in SN2 chemical reactions where S – adenosylmethionine behaves like a methylating agent.
Organic sulphides examples
Some organic sulphide examples are dimethyl sulphide, trimethylsulphonium iodide, trithiacyclononane, etc. These sulphides can be readily oxidized to produce sulfones. The sulfonium salts are produced by the alkylation of sulphides. Lastly, it is possible to produce thioether complexes by binding organic sulphides to metals. An example of such a complex is trithiacyclononane.
Conclusion
Organosulphur chemistry indicates organic sulphides as a separate functional group that characterizes the linkage C – S – C. Here both the Cs represent either an aryl or alkyl group or both simultaneously. We are assured that somewhat the properties of organic sulphides resemble that of ethers. This is a conclusion that we derive from the relative positions of sulphur and oxygen in the periodic table.
