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Kinetics and mechanism of alkaline hydrolysis of Y-substituted phenyl phenyl carbonates

Title
Kinetics and mechanism of alkaline hydrolysis of Y-substituted phenyl phenyl carbonates
Authors
Kim S.-I.Hwang S.-J.Jung E.-M.Um I.-H.
Ewha Authors
엄익환
SCOPUS Author ID
엄익환scopusscopus
Issue Date
2010
Journal Title
Bulletin of the Korean Chemical Society
ISSN
0253-2964JCR Link
Citation
vol. 31, no. 7, pp. 2015 - 2018
Indexed
SCI; SCIE; SCOPUS; KCI WOS scopus
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.
DOI
10.5012/bkcs.2010.31.7.2015
Appears in Collections:
자연과학대학 > 화학·나노과학전공 > Journal papers
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