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Organic sulfide
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Organic sulfide
In organic chemistry, a sulfide (British English sulphide) or thioether is an organosulfur functional group with the connectivity R−S−R' as shown on right. Like many other sulfur-containing compounds, volatile sulfides have foul odors. A sulfide is similar to an ether except that it contains a sulfur atom in place of the oxygen. 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.
Sulfides are sometimes called thioethers, especially in the old literature. The two organic substituents are indicated by the prefixes. (CH3)2S is called dimethylsulfide. Some sulfides are named by modifying the common name for the corresponding ether. For example, C6H5SCH3 is methyl phenyl sulfide, but is more commonly called thioanisole, since its structure is related to that for anisole, C6H5OCH3.
The modern systematic nomenclature in chemistry for the trival name thioether is sulfane.
Sulfide is an angular functional group, the C–S–C angle approaching 90° The C–S bonds are about 180 pm. For the prototype, dimethylsulfide, the C-S-C angles is 99°, which is smaller than the C-O-C angle in ether (~110°). The C-S distance in dimethylsulfide is 1.81 Å.
Sulfides are characterized by their strong odors, which are similar to thiol odor. This odor limits the applications of volatile sulfides. In terms of their physical properties they resemble ethers, but are less volatile, higher melting, and less hydrophilic. These properties follow from the polarizability of the divalent sulfur center, which is greater than that for oxygen in ethers.
Thiophenes are a special class of sulfide-containing heterocyclic compounds. The nonbonding electrons on sulfur are delocalized into the aromatic π-system. As a consequence, thiophene exhibits few properties expected for a sulfide – thiophene is non-nucleophilic at sulfur and, in fact, is sweet-smelling. Upon hydrogenation, thiophene gives tetrahydrothiophene, C4H8S, which indeed does behave as a typical sulfide.
Sulfides are important in biology, notably in the amino acid methionine and the cofactor biotin. Petroleum contains many organosulfur compounds, including sulfides. Polyphenylene sulfide is a useful high temperature plastic. Coenzyme M, CH
3SCH
2CH
2SO−
3, is the precursor to methane (i.e. natural gas) via the process of methanogenesis.
Sulfides are typically prepared by alkylation of thiols. Alkylating agents include not only alkyl halides, but also epoxides, aziridines, and Michael acceptors.
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Organic sulfide
In organic chemistry, a sulfide (British English sulphide) or thioether is an organosulfur functional group with the connectivity R−S−R' as shown on right. Like many other sulfur-containing compounds, volatile sulfides have foul odors. A sulfide is similar to an ether except that it contains a sulfur atom in place of the oxygen. 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.
Sulfides are sometimes called thioethers, especially in the old literature. The two organic substituents are indicated by the prefixes. (CH3)2S is called dimethylsulfide. Some sulfides are named by modifying the common name for the corresponding ether. For example, C6H5SCH3 is methyl phenyl sulfide, but is more commonly called thioanisole, since its structure is related to that for anisole, C6H5OCH3.
The modern systematic nomenclature in chemistry for the trival name thioether is sulfane.
Sulfide is an angular functional group, the C–S–C angle approaching 90° The C–S bonds are about 180 pm. For the prototype, dimethylsulfide, the C-S-C angles is 99°, which is smaller than the C-O-C angle in ether (~110°). The C-S distance in dimethylsulfide is 1.81 Å.
Sulfides are characterized by their strong odors, which are similar to thiol odor. This odor limits the applications of volatile sulfides. In terms of their physical properties they resemble ethers, but are less volatile, higher melting, and less hydrophilic. These properties follow from the polarizability of the divalent sulfur center, which is greater than that for oxygen in ethers.
Thiophenes are a special class of sulfide-containing heterocyclic compounds. The nonbonding electrons on sulfur are delocalized into the aromatic π-system. As a consequence, thiophene exhibits few properties expected for a sulfide – thiophene is non-nucleophilic at sulfur and, in fact, is sweet-smelling. Upon hydrogenation, thiophene gives tetrahydrothiophene, C4H8S, which indeed does behave as a typical sulfide.
Sulfides are important in biology, notably in the amino acid methionine and the cofactor biotin. Petroleum contains many organosulfur compounds, including sulfides. Polyphenylene sulfide is a useful high temperature plastic. Coenzyme M, CH
3SCH
2CH
2SO−
3, is the precursor to methane (i.e. natural gas) via the process of methanogenesis.
Sulfides are typically prepared by alkylation of thiols. Alkylating agents include not only alkyl halides, but also epoxides, aziridines, and Michael acceptors.
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