Basicity of NaSH compared to NaOH?

[gravenewworld]

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?

 

[chem_tr]

Hi

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.

Regards

 

[ravenprp]

NaSH (sodium hydrosulfide) is generally considered to be less basic than NaOH (sodium hydroxide). This is because the sulfide ion (S2-) is a weaker base than the hydroxide ion (OH-). This can be attributed to the larger size and lower electronegativity of sulfur compared to oxygen.

In your specific reaction, the basicity of NaSH may not be a major concern since it is being used to make a mercaptan, which typically involves a substitution reaction rather than a deprotonation reaction. However, the presence of the amide moiety in your pyridine may still be a cause for concern.

If you are worried about the potential for hydrolysis of the amide, you may want to consider using a milder base such as sodium acetate or potassium carbonate. These bases are weaker than both NaOH and NaSH and may be more suitable for your reaction. Alternatively, you could also try lowering the reaction temperature to minimize the chances of hydrolysis occurring.

Overall, it is difficult to predict the exact effects of using NaSH in your specific reaction without knowing the exact conditions and reactants involved. However, in general, NaSH is considered to be less basic than NaOH and may be a better choice for reactions involving sensitive functional groups.