Home page
About
Chemogenesis web book
Chemical Thesaurus
Tutorials and Drills
Meta-Synthesis Shop
Reviews
Contact Us
Links Page
Frequently Asked Questions

Ambidentate Behaviour: Selectivity of beta-propiolactone
According to Pearsons hard soft [Lewis] acid base principle, hard Lewis acids have a strong affinity for hard Lewis bases and soft Lewis acids have a strong affinity for soft Lewis bases.

beta-Propiolactone reacts with hard nucleophiles (such as HO-) by acylation, and soft nucleophiles by alkylation.

Note that while hard vs soft comparisons can be made for carefully selected pairs of species and/or reactive centres, the HSAB analysis is NOT general. For more information look in the Chemogenesis webbook section on Pearson's HSAB principle.