Nucleofiles and Bases (Organic Chemistry)
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5 Terms
Nucleofile
an electron rich species (negatively charged or has lone pair or pi bond).
Nucleophilicity and basicity often go hand in hand; strong bases are usually strong nucleophiles.
Generally, a negatively charged nucleofile (Nu-) is
a strong nucleofile and a strong base
Generally a neutral nucleofile is a
weak Nu and weak base.
However, nucleophilicity also takes into account steric effects. Therefore, a strong nucleophile MUST be sterically unhindered.
Examples of good base but a BAD nucleofile
potassium t-butoxide (KOtBu) and lithium diisopropyl amide (LDA). They are negatively charged but are sterically hindered.
Examples of good nucleofile but a BAD base
X- (Br-, Cl-, I-), -CN (cyanide), -OAc (acetate), N3- (azide), -SR (thiolate).
These are conjugate bases of acids with a pKa of less than 10 so they are weak bases.
