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Thiophenol is a chemical compound with the formula C6H5SH, and sometimes abbreviated as PhSH. The foul-smelling liquid is the principal aromatic thiol. The chemical structures of thiophenols are analogous to phenols except the oxygen atom in the hydroxyl group (-OH) bonded to the aromatic ring is replaced by a sulfur atom. The prefix thio- implies a sulfur-containing compound and when used before a root word name for a compound which would normally contain an oxygen atom, thio- commonly means that the oxygen atom is replaced by a sulfur atom.
Thiophenols also describes a class of compounds formally derived from thiophenol itself. All have a sulfhydryl group (-SH) covalently bonded to an aromatic ring. The organosulfur ligand in medicine merthiolate is a thiophenol.
Many ways exist to generate thiophenol and related compounds, although thiophenol is usually purchased for laboratory operations.
Thiophenol has appreciably greater acidity than does phenol. A similar pattern is seen for H2S vs. H2O and all thiols vs. the corresponding alcohols. Treatment of PhSH with strong base such as sodium hydroxide (NaOH) or sodium metal affords the salt sodium thiophenolate (PhSNa). Such salts are readily oxidized.
The thiophenolate is highly nucleophilic, which translates to an high rate of alkylation. Thus, treatment of C6H5SH with methyl iodide in the presence of a base gives methyl phenyl sulfide, C6H5SCH3, a thioether. Such reactions are fairly irreversible. C6H5SH also adds to α,β-unsaturated carbonyls.
A substantial difference between sulfur and oxygen is that thiophenolate is oxidized to diphenyl disulfide:
The disulfide can be reduced back the thiol using sodium borohydride followed by acidification. This redox reaction is also exploited in the use of C6H5SH as a source of H atoms. Of course free H atoms are almost never observed in solution, but C6H5SH delivers the equivalent result by adding H atoms to various substrates.
Coordination to metals
Thiophenol is highly toxic.
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Thiophenol". A list of authors is available in Wikipedia.|