edwardx
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Thiol vs. alcohol as a nucleophile
Since alcohols are stronger bases than thiols, you would expect alcohols to be better nucleophiles in substitution and elimination reaction than
thiols! But because sulfur is larger than oxygen it is less solvated by a protic solvent, and because it is more polarizable, it is actually a better
nucleophile(in protic solvents). My question is: Are thiols still better nucleophiles in aprotic solvent? Or does the lesser solvation of alcohols
in aprotic solvents, cause the more electronegative alcohol to be the better nucleophile?
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Chemosynthesis
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This should be posted in Beginnings.
Size and polarizability are the primary determinants of nucleophilicity in protic solvents. Basicity/electronegativity is the primary determinant in
aprotic solvents.
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Bert
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Thread Moved
9-11-2014 at 16:54 |
CuReUS
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you can see this video ,it is very helpful
https://www.khanacademy.org/science/organic-chemistry/substi...
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