Competition between basicity and nucleophilicity
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.