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Competition of basicity and nucleophilicity

The diisopropylamide anion is a strong, non-nucleophilic base.

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If it is bulky and sterically-demanding, a strong base may be a particularly poor nucleophile. Lithium diisopropylamide (LDA), for instance, is an extremely strong base that is frequently applied to the generation of carbanions in the laboratory. Due to the shielding caused by its bulky, sterically-demanding isopropyl groups, the nitrogen is not nucleophilic, though it is negatively charged and possesses two lone electron pairs.