|
KMID : 1059519940380120915
|
|
Journal of the Korean Chemical Society
1994 Volume.38 No. 12 p.915 ~ p.920
|
|
|
Structure-Reactivity Relationship of Benzylbenzenesulfonates (Part Ⅰ.) Mechanism of the Reaction of Benzylbenzenesulfonates with Pyridines
|
|
Chung Duck-Young
Park Jong-Hwan
Kwon Jeong-Min
Yoh Soo-Dong
Shim Kwnag-Taik
|
|
|
Abstract
|
|
|
|
The Menschutkin type reactions of substituted (Z)-benzyl (X)-arenesulfonates with substituted(Y)-pyridines were studied by the electroconductometric method in acetonitrile at 35℃. Hammett ρ values were calculated by the second order rate constants for the reaction of substituted (Z)-benzyl (X)-arenesulfonates with substituted (Y)-pyridines. The negative ρY values meant positive charge development on the nitrogen of pyridine at transition state owing to the charge development on the oxygen atom of benzenesulfonate. And the negative ρZ values meant positive charge development on the benzylic carbon. Application of the multi-Hammett interaction,│ρYZ│ > │ρXY│ > │ρZX│, the Menschutkin type reaction of substituted benzyl arenesulfonates with substituted pyridines was shown to be dissociative SN2 mechanism.
|
|
|
KEYWORD
|
|
|
|
|
|
FullTexts / Linksout information
|
|
|
|
|
|
Listed journal information
|
|
|