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The effect of medium on rate and mechanism: Aminolysis of O-4-nitrophenyl thionobenzoate in MeCN and H2O

Title
The effect of medium on rate and mechanism: Aminolysis of O-4-nitrophenyl thionobenzoate in MeCN and H2O
Authors
Um I.-H.Seok J.-A.Kim H.-T.Bae S.-K.
Ewha Authors
엄익환
SCOPUS Author ID
엄익환scopusscopus
Issue Date
2003
Journal Title
Journal of Organic Chemistry
ISSN
0022-3263JCR Link
Citation
vol. 68, no. 20, pp. 7742 - 7746
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
Pseudo-first-order rate constants (kobs) have been measured spectrophotometrically for reactions of O-4-nitrophenyl thionobenzoate (1) with a series of alicyclic secondary amines in MeCN and H2O at 25.0 ± 0.1 °C. The plot of kobs vs amine concentration exhibits an upward curvature in all cases, indicating that the reactions proceed through two tetrahedral intermediates (a zwitterionic T ± and its deprotonated anionic T-) regardless of the amine basicity and the nature of the reaction medium. However, all the amines investigated have been found to be much less reactive in MeCN than in H2O, although the amines are more basic in the former medium by 7-9 pKa units.
DOI
10.1021/jo034637n
Appears in Collections:
자연과학대학 > 화학·나노과학전공 > Journal papers
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