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Chemistry LibreTexts

Ambident Nucleophile

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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.

ambidentnucleophile1.png

The hybrid can be drawn roughly as follows.

ambidentnucleophile2.png

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This page titled Ambident Nucleophile is shared under a All Rights Reserved (used with permission) license and was authored, remixed, and/or curated by Gamini Gunawardena via source content that was edited to the style and standards of the LibreTexts platform.

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