|
KMID : 1059519920360040589
|
|
Journal of the Korean Chemical Society
1992 Volume.36 No. 4 p.589 ~ p.597
|
|
|
Hydrolysis Mechanism of Phenyl-N-benzoylchlorothioformimidate Derivatives
|
|
Kwon Ki-Sung
Kim Chon-Suk
Lee Yong-Gu
Sung Nack-Do
|
|
|
Abstract
|
|
|
|
The rate constants of hydrolysis of phenyl-N-benzoylchlorothioformimidates were determined by UV spectrophotometry in 30% (v/v) aqueous dioxane at 25℃. On the basis of rate equation, general base catalysis, solvent effect, substituent effect, thermodynamic parameters, frontier orbital interaction and hydrolysis product analysis, it may be concluded that the hydrolysis of phenyl-N-benzoylchlorothioformimidates proceeds through SN1 mechanism via azocarbocation intermidiate below pH 10.0, while above pH 10.00 the hydrolysis proceeds through nucleophilic addition-elimination (AdN-E) mechanism. In the range of pH from 10.0 to 11.0 these two reaction occur competitively.
|
|
|
KEYWORD
|
|
|
|
|
|
FullTexts / Linksout information
|
|
|
|
|
|
Listed journal information
|
|
|