Non-nucleophilic base

A base that accepts a proton but has little tendency to attack electrophilic atoms. It can promote deprotonation while limiting competing nucleophilic substitution.

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Proton transfer: The movement of a proton from one chemical species to another. The defining reaction these bases promote is removal of a proton.
Lithium diisopropylamide: A strong, sterically hindered lithium amide base widely used in organic synthesis. LDA is a standard choice for generating enolates while limiting direct nucleophilic attack.
Nucleophile: An electron-pair donor that forms a bond to an electron-deficient atom. Unlike a deliberately hindered base, a nucleophile is valued for attacking electrophilic centers.
Basicity: The tendency of a species to accept a proton. It measures proton affinity, the property a non-nucleophilic base must retain.
Steric hindrance: Reduced reactivity caused by atoms or groups obstructing access to a reactive site. Bulky groups can obstruct approach to electrophilic atoms while leaving proton abstraction possible.
Potassium tert-butoxide: A bulky alkoxide base used in organic synthesis and elimination reactions. Its steric bulk often favors proton abstraction over substitution, though it can still act as a nucleophile.
Nucleophilic substitution: A reaction in which a nucleophile replaces a leaving group on an electrophile. Suppressing this competing pathway is a central reason to choose a non-nucleophilic base.
Nucleophilicity: The tendency of a species to donate an electron pair to an electrophile. Low nucleophilicity, rather than low basicity, defines the selectivity sought here.
Conjugate acid: The species formed when a base accepts a proton. Its acidity helps determine how strongly a base favors deprotonation.
Sodium hydride: An ionic hydride reagent used to deprotonate compounds in organic synthesis. Hydride rapidly accepts protons, and released hydrogen gas helps drive deprotonation.