Current time in Korea 13:39 Oct 22 (Sun) Year 2017 KCS KCS Publications
KCS Publications
My Journal Log In Register
HOME > Search > Browsing(BKCS) > Archives

Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 31, Number 7
BKCSDE 31(7)
July 20, 2010 

 
Title
Kinetics and Mechanism of Alkaline Hydrolysis of Y-Substituted Phenyl Phenyl Carbonates
Author
Song I Kim, So Jeong Hwang, Eun Mi Jung, Ik Hwan Um*
Keywords
Alkaline hydrolysis, Concerted mechanism, Inductive effect, Hammett plot, Yukawa-Tsuno plot
Abstract
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.
Page
2015 - 2018
Full Text
PDF