81256-74-8Relevant articles and documents
Kinetics and mechanism of alkaline hydrolysis of Y-substituted phenyl phenyl carbonates
Kim, Song-I,Hwang, So-Jeong,Jung, Eun-Mi,Um, Ik-Hwan
experimental part, p. 2015 - 2018 (2010/12/19)
Second-order rate constants (kOH-) have been measured spectrophotometrically for alkaline hydrolysis of Y-substituted phenyl phenyl carbonates (2a-j) and compared with the kOH- values reported previously for the corresponding reactions of Y-substituted phenyl benzoates (1a-j). Carbonates 2a-j are 8 ~ 16 times more reactive than benzoates 1a-j. The Hammett plots correlated with σ- and σo constants exhibit many scattered points, while the Yukawa-Tsuno plot results in excellent linear correlation with ρ = 1.21 and r = 0.33. Thus, the reaction has been concluded to proceed through a concerted mechanism in which expulsion of the leaving group is advanced only a little. However, one cannot exclude a possibility that the current reaction proceeds through a forced concerted mechanism with a highly unstable intermediate.