Penicillenic acid, the mechanism of the acid and base catalysed hydrolysis reactions

Abstract

Rate coefficient data are reported for the hydrolysis of benzyl penicillenic acid over pH range 0·5–14. The complex rate –pH profile, containing six changes in acidity dependence, is analysed in terms of the dissociation constants and relative reactivities of the tautomeric species present. The yields of the four known reaction products at various pH's provide quantitative support for the mechanistic interpretation.