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Some sulfides are named by modifying the common name for the corresponding ether. For example, C 6 H 5 SCH 3 is methyl phenyl sulfide, but is more commonly called thioanisole, since its structure is related to that for anisole, C 6 H 5 OCH 3. The modern systematic nomenclature in chemistry for the trival name thioether is sulfane. [2]
Akin to the chemistry of alcohols, thiols form sulfides, thioacetals, and thioesters, which are analogous to ethers, acetals, and esters respectively. Thiols and alcohols are also very different in their reactivity, thiols being more easily oxidized than alcohols. Thiolates are more potent nucleophiles than the corresponding alkoxides.
Some metal sulfides, when exposed to a strong mineral acid, including gastric acids, will release toxic hydrogen sulfide. Organic sulfides are highly flammable. When a sulfide burns it produces sulfur dioxide (SO 2) gas. Hydrogen sulfide, some of its salts, and almost all organic sulfides have a strong and putrid stench; rotting biomass ...
Humans and other animals have an exquisitely sensitive sense of smell toward the odor of low-valent organosulfur compounds such as thiols, sulfides, and disulfides. Malodorous volatile thiols are protein-degradation products found in putrid food, so sensitive identification of these compounds is crucial to avoiding intoxication.
Thiophenol is an organosulfur compound with the formula C 6 H 5 SH, sometimes abbreviated as PhSH. This foul-smelling colorless liquid is the simplest aromatic thiol.The chemical structures of thiophenol and its derivatives are analogous to phenols, where the oxygen atom in the hydroxyl group (-OH) bonded to the aromatic ring in phenol is replaced by a sulfur atom.
Ethanethiol, commonly known as ethyl mercaptan, is an organosulfur compound with the formula CH 3 CH 2 SH. [5] It is a colorless liquid with a distinct odor. Abbreviated EtSH, it consists of an ethyl group (Et), CH 3 CH 2, attached to a thiol group, SH.
It is produced industrially by the hydrogenation of cyclohexanone in the presence of hydrogen sulfide over a metal sulfide catalyst: C 6 H 10 O + H 2 S + H 2 → C 6 H 11 SH + H 2 O. It is also obtained by the addition of hydrogen sulfide to cyclohexene in the presence of nickel sulfide. [2]
Thiourea is employed as a source of sulfide, such as for converting alkyl halides to thiols. The reaction capitalizes on the high nucleophilicity of the sulfur center and easy hydrolysis of the intermediate isothiouronium salt: CS(NH 2) 2 + RX → RSC(NH 2) + 2 X − RSC(NH 2) + 2 X − + 2 NaOH → RSNa + OC(NH 2) 2 + NaX + H 2 O RSNa + HCl ...