Ambident nucleophiles, like cyanides and nitrites, have two nucleophilic centers. Cyanide can act through the carbon atom (⁻C≡N) or nitrogen atom (⁻:C=N⁻), forming alkyl cyanides or isocyanides. Similarly, nitrite ion can link through oxygen (⁻O—:N=O) to form alkyl nitrites or through nitrogen atom, leading to nitroalkanes.
What distinguishes ambident nucleophiles, and provide examples of groups that possess two nucleophilic centers?
Share
Ambident nucleophiles possess two distinct nucleophilic centers within the same molecule. These centers can potentially participate in nucleophilic attacks. Examples include nitrite ions (NO2⁻), where nitrogen and oxygen can act as nucleophiles, attacking electrophiles at different positions. Another example is the enolate ion, where the carbon and oxygen atoms can function as nucleophiles during reactions. Ambident nucleophiles offer versatility in reactions by allowing nucleophilic attacks at multiple sites, influencing the regioselectivity and product formation in various chemical processes. Nitrite ion and enolate ion are notable examples showcasing the ambident reactivity of certain functional groups.