An ambident nucleophile is a nucleophile with two nucleophilic sites, meaning it has two sites through which it can attack. These nucleophiles can execute nucleophilic attacks from two or more different places in the molecule or ion, often resulting in the formation of more than one product. The negative charge of the ion is delocalized over two different atoms by resonance effects. Examples of ambident nucleophiles include:

• Thiocyanate ion (SCN-): This ion can execute nucleophilic attacks from either the sulfur atom or the nitrogen atom, resulting in the formation of a mixture of products.

• Cyanide ion (CN-): This ion has two nucleophilic sites, one on carbon and one on nitrogen, and can form a bond with two centers.

• Nitrite ion (NO2-): This ion can attack through oxygen, resulting in the formation of alkyl nitrites, or through nitrogen, resulting in the formation of nitroalkanes.

Ambident nucleophiles are important in organic chemistry because they can lead to the formation of multiple products, which can be useful in the synthesis of complex molecules.