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Basicity of NaSH compared to NaOH?

  1. Nov 22, 2006 #1
    I am using NaSH to make a mercaptan by refluxing a bromo pyridine in ethanol. The only thing is that my pyridine also has an amide moiety, and I am afraid of the basicity of NaSH (since S is 1 below O on the periodic table). If I reflux this reaction I am afraid I might hydrolyze off the amide, so I was wondering, how basic is NaSH compared to NaOH?
  2. jcsd
  3. Nov 28, 2006 #2


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    I think it is less basic than NaOH, since the acidic adduct of NaSH is H2S, where NaOH produces H2O. Since the former product is more acidic, the parent compound (NaSH) must be less basic.

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