Nucleophilicity
roughly parallels basicity. The trick lies within the word roughly. A base (in
a BL sense) attacks protons, whereas a nucleophile attacks anything else.
From
here, try to think about this: basicity is a subset of nucleophilicity. All
nucleophiles are Lewis bases; they donate a lone pair of electrons. A “base”
(or, better said, a Brønsted base) is just the name we give to a nucleophile
when iit forms a bond to a proton (H+). Therefore, when we are talking about
basicity and nucleophilicity, we are describing these two types of events.
If
basicity can be described by means of equilibria, nucleophilicity can be
described in terms of reaction rates. Acid-base reactions are fast equilibria.
Many
reactions of nucleophiles are not reversible and two more factors must be
accounted for, though, when dealing with nucleophiles: their steric hindrance
and solvent effects. The more sterically hindered a nucleophile, the weaker it
is. The more polar (or, even worse, the more protic) a solvent, the weaker the
nucleophile.
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