150831-99-5Relevant academic research and scientific papers
The Quest for Carbanion-promoted Dissociative Pathways in the Hydrolysis of Aryl Phosphinates
Cevasco, Giorgio,Thea, Sergio
, p. 1103 - 1106 (2007/10/02)
Results of a kinetic study on the alkaline hydrolysis of the aryl(methylsulfonyl)methylphenylphosphinates 3a-i show that a dissociative mechanism is not operating in this reaction.Activation entropy data (ΔS = -59.5 J mol-1 K-1 for the 4-nitrophenyl ester) and good Hammett ? relationship (ρ = 1.45 +/- 0.07) strongly suggest that an associative bimolecular mechanism occurs, in which negligible negative charge is generated on the leaving group in the rate-determining step.
