ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 36, Number 4
JKCSEZ 36(4)
August 20, 1992 

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 (Ad_N-E) mechanism. In the range of pH from 10.0 to 11.0 these two reaction occur competitively.