Does anyone know if is it possible to deprotonate a thiol compound with secondary or primary amine (cyclohexylamine or piperidine) to obtain thiolate?

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Zach Erno

Yes. The fact that the pKa of the thiol is one unit lower than that of the secondary ammonium ion indicates that the thiol is sufficiently acidic to transfer its proton to the corresponding amine.

Mathieu Morency

Zach Erno Do you have a reference about that? What about alkyne thiol with pyridine for instance? I know that the pKa of alkyne thiol is about 11 and the pKa of the pyridine is about 5. But from experiments that I did, it seems that the thiol still get deprotonated. Do you have an explanation for that? Thanks.