Nucleophiles

There are a number of methods of classifying nucleophilic ability. See the notes for general trends. The following lists give examples of relative nucleophilicity. Note that nucleophilic ability will change slightly from reaction to reaction, as mechanism changes and as the structure of the electrophile changes.

Relative Nucleophilicity in polar solvents

O SH > C N > I > OH > N N N > Br > O > Cl > H2O

Strong Nucleophiles
(CH3)3P SH C N I (CH3)2NH (CH3)3N OH

"Medium" Nucleophiles
Br NH3 Cl O O

Weak Nucleophiles
H2O F

You can classify related compounds in each series. For example, OH- is a strong nucleophile, as are other alkoxides such as CH3O-. Be sure to consider all factors when deciding nucleophilicity. Although CH3O- is a stong nucleophile, (CH3)3CO- is not because of hindrance.