carbanionlike
Carbanionlike describes a class of chemical species in which a carbon atom bears substantial negative charge density and behaves as a nucleophilic center in reactions, closely resembling a carbanion, even if the formal negative charge is delocalized over adjacent atoms or a metal center. The term emphasizes carbon-centered reactivity that arises from carbanion character rather than from a discrete, isolated anion.
Stabilization of carbanionlike centers occurs through resonance with adjacent carbonyl groups or other pi systems, as
Representative examples include enolates and related alpha-substituted carbonyl anions, malonates and other beta-dicarbonyl systems, nitrile-stabilized carbanions,
Reactivity and applications: carbanionlike species act as nucleophiles toward electrophiles such as carbonyl compounds, alkyl halides,