Is a thiol group an ortho/para director on a benzene ring?
I can't figure out if the sulfur in a thiol group will add a resonance structure to the ortho/para positions by moving one of its lone pairs into a bond or not...
Answer:
In general, anything that puts a lone pair of electrons adjacent to the aromatic ring will be ortho-para directing. This rule even applies to the halogens (Cl, Br), which are curiously ortho-para directing even though they are deactivating (because of their inductive electron-withdrawing effect).
This would include divalent sulfur, as in a thiol.
I would expect a benzenethiol, however, to suffer side reactions such as oxidation of the sulfur atom, in direct halogenations.
Since sulfur is in the same family as oxygen, I would expect the thiol group on a benzene ring to act like an oxygen, just not as actively. Yes, sulfur can move electron pairs around to form double bonds. I would expect the -SH group to be ortho-para directing.
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