Ambident Nucleophile
- Page ID
- 33804
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An ambident nucleophile is an anionic nucleophile whose negative charge is delocalized by resonance over two unlike atoms or over two like but non-equivalent atoms. The most common ambident nucleophiles are enolate ions. For example, the resonance forms of acetone enolate are shown below.
The hybrid can be drawn roughly as follows.
- Gamini Gunawardena from the OChemPal site (Utah Valley University)