As the oil ages, the thiols and sulfides are slowly converted into more stable compounds such as benzothiophene. Most crude oils contain organosulfur compounds such as thiols, sulfides, and polysulfides, presumably formed from the reaction of hydrocarbons with elemental sulfur, in turn generated from microbial action on sulfate in rocks. Polyphenylene sulfide (see below) has the empirical formula C6H4S. Halosulfonium ions and related species formed from sulfoxides are key intermediates in the synthesis of polysaccharides from 1-phenylthioglycosides, facilitating replacement of the phenylthio, PhS (or phenylsulfinyl, PhS(O)), group by a nucleophile from a second saccharide molecule, joining the saccharides in a process termed glycosylation. Indeed, the 2000 Nobel Prize for Chemistry, awarded to American chemists Alan J. Heeger and Alan G. MacDiarmid and Japanese chemist Shirakawa Hideki, recognized the discovery of plastics that conduct electricity. For example, S-adenosylmethionine acts as a methylating agent in biological SN2 reactions. One-electron oxidation of sulfides gives radical cations, of importance in conducting materials; these radical cations can dimerize to give dithia dications, R2S+―S+R2, which can also be formed in reactions involving bis-sulfides, molecules with two spatially separated sulfide groups. A disulfide is a compound containing an -S-S- linkage. Corrosion is a major concern in many industrial installations processing sulfides: sulfide ore mills, deep oil wells, pipelines transporting soured oil, Kraft paper factories. As a consequence, thiophene exhibits few properties expected for a sulfide – thiophene is non-nucleophilic at sulfur and, in fact, is sweet-smelling. (CH3)2S is called dimethylsulfide. The grouping of oxygen and sulfur in the periodic table suggests that the chemical properties of ethers and sulfides are somewhat similar, though the extent to which this is true in practice varies depending on the application. If one of the carbon groups, R, in a sulfide RSR′ is olefinic, aromatic, or acetylenic and the other group, R′, is a saturated carbon (e.g., methyl or ethyl), the bond to the saturated carbon can be cleaved with sodium or lithium metal in liquid ammonia—for example, RSR′ + Na/NΗ3→ RSNa + R′―H. Learn about the chemistry of garlic and why it causes bad breath and is good for health. Microbially-induced corrosion (MIC) or biogenic sulfide corrosion are also caused by sulfate reducing bacteria producing sulfide that is emitted in the air and oxidized in sulfuric acid by sulfur oxidizing bacteria. The sulfide functional group consists of a S atom bonded to two C atoms via s bonds. Such inorganic sulfides typically have very low solubility in water, and many are related to minerals with the same composition (see below). 181 pm) are longer than analogous C-O bonds (approx. This article is about sulfur anion in general. In terms of their physical properties they resemble ethers, but are less volatile, higher melting, and less hydrophilic. The C-S distance in dimethylsulfide is 1.81 Å.. The nonbonding electrons on sulfur are delocalized into the π-system.  Instead sulfide converts to hydrosulfide: Upon treatment with an acid, sulfide salts convert to hydrogen sulfide: Oxidation of sulfide is a complicated process. methanethiol, or methyl mercaptan. For example, allyl methyl sulfide is a major contributor to human “garlic breath.”. Polyphenylene sulfide (see below) has the empirical formula C6H4S. Some sulfides are named by modifying the common name for the corresponding ether. Many important metal ores are sulfides. The high polarizability of sulfur stabilizes a negative charge on the carbon adjacent to divalent sulfur, as in RSCH2−(usually as α-lithium sulfides, RSCH2Li), which proves useful in organic synthesis through nucleophilic reaction with alkylating agents and carbonyl compounds. For example, dimethyl sulfide can be oxidized as follows: Ethers can be alkylated at oxygen only with difficulty, but sulfides are readily alkylated to give stable sulfonium salts, such as trimethylsulfonium iodide: In analogy to their easy alkylation, sulfides bind to metals to form thioether complexes. (The use of the alternative name sulphoxide is discouraged by IUPAC.) By signing up for this email, you are agreeing to news, offers, and information from Encyclopaedia Britannica. Sulfides are typically prepared by alkylation of thiols: Such reactions are usually conducted in the presence of a base, which converts the thiol into the more nucleophilic thiolate. Sulfide is an angular functional group, the C–S–C angle approaching 90° The C–S bonds are about 180 pm. Occasionally, the term sulfide refers to molecules containing the –SH functional group. Be on the lookout for your Britannica newsletter to get trusted stories delivered right to your inbox. Sulfide also refers to chemical compounds large families of inorganic and organic compounds, e.g. Like thiols, sulfides can form metal complexes, particularly in the case of cyclic polysulfides with crown etherlike structures, such as the hexathia-18-crown-6. In nature, sulfides can serve as ligands, as in cytochrome C, in which the sulfur of methionine is coordinated to the heme iron. Metal sulfides react with halogens, forming sulfur and metal salts. In molecules with other functional groups of higher priority, the sulfide group is designated by thio- (as in thiodiacetic acid, HO2CCH2SCH2CO2H) or by methylthio- (as in methylthioacetic acid, CH3SCH2CO2H). Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions.
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