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Chemistry LibreTexts

Ambident Nucleophile

[ "article:topic", "authorname:ggunawardena" ]
  • Page ID
    33804
  • 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.

     

    ambidentnucleophile1.png

     

    The hybrid can be drawn roughly as follows.

    ambidentnucleophile2.png

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