How Basic is NaSH Compared to NaOH in Organic Synthesis?

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In summary, the conversation is about a person using NaSH to make a mercaptan by refluxing a bromo pyridine in ethanol. However, the pyridine also has an amide moiety and they are concerned about the basicity of NaSH compared to NaOH. The individual suggests that NaSH is less basic than NaOH because its acidic adduct, H2S, is more acidic.
  • #1
gravenewworld
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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?
 
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  • #2
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
 
  • #3

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.
 

Related to How Basic is NaSH Compared to NaOH in Organic Synthesis?

1. What is the basicity of NaSH compared to NaOH?

The basicity of a compound refers to the number of hydrogen ions (H+) that can be released by one molecule of the compound in an aqueous solution. NaSH (sodium hydrosulfide) has a basicity of 2, meaning that one molecule of NaSH can release two hydrogen ions. On the other hand, NaOH (sodium hydroxide) has a basicity of 1, as one molecule of NaOH can release only one hydrogen ion.

2. Why does NaSH have a higher basicity than NaOH?

The basicity of a compound is determined by the number of hydrogen ions that can be released by the compound's conjugate acid. In the case of NaSH and NaOH, the conjugate acid of NaSH (H2S) has two hydrogen ions, while the conjugate acid of NaOH (H2O) has only one. This is why NaSH has a higher basicity than NaOH.

3. How does the basicity of NaSH and NaOH affect their properties?

The basicity of a compound is a measure of its ability to neutralize acids. Therefore, a higher basicity means that a compound is more alkaline and has a stronger ability to neutralize acids. In the case of NaSH and NaOH, NaSH is more basic and therefore has a stronger alkaline nature compared to NaOH.

4. Is NaSH more corrosive than NaOH due to its higher basicity?

The basicity of a compound does not necessarily determine its corrosiveness. Both NaSH and NaOH are highly corrosive compounds due to their ability to react with and break down other substances. In fact, NaOH is typically considered more corrosive than NaSH due to its strong alkaline nature and ability to cause severe chemical burns.

5. Can NaSH and NaOH be used interchangeably in basic solutions?

No, NaSH and NaOH cannot be used interchangeably in basic solutions. Although both compounds are strong bases, they have different basicities and therefore different properties. NaSH is usually used in industries where a stronger alkaline solution is needed, while NaOH is commonly used in household products and in water treatment processes.

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