zum Directory-modus

Competition between basicity and nucleophilicity

LDA, a non-nucleophilic base

Ball & Stick Spacefill Put back

A strong base may be a poor nucleophile if it is considerably bulky. Lithium diisopropylamide (LDA) is one such base. Due to its sterically-demanding isopropyl substituents, LDA is frequently used in laboratory-scale syntheses.

Nucleophilicity is a kinetic measure that describes how rapidly a nucleophile reacts in a nucleophilic attack. In contrast, basicity is a thermodynamic measure, which merely describes the equlibrium.