
TY  - JOUR
A1  - Crow, WD 
A1  - Gosney, I 
T1  - Isothiazole chemistry. IV. Cyanide cleavage of the S-N bond in 3-hydroxyisothiazole
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1967
VL  - 20
IS  - 12
SP  - 2729
EP  - 2736
KW  - 
UR  - https://doi.org/10.1071/CH9672729 
N2  - Nucleophilic attack on 3-hydroxyisothiazole by cyanide ion, yielding cis-3-thiocyanoacrylamide, has been investigated over the pH range 0.00-5.50. Rate constants have been measured both for direct attack by cyanide ion and from the effect of cyanide ion in retarding the cyclization of the thiocyanoacrylamide; in both cases the derived rate constants agree. The pH-rate profile of the reaction reveals the existence of two kinetically discrete mechanisms. Within the range 5.50-4.00 the dominating mechanism is one involving a slow direct attack on 3-hydroxyisothiazole itself, while at pH less than 3.50 the conjugate acid of this molecule is subjected to a much faster attack. Equilibrium studies have been made for the system, and the effect of temperature on the equilibrium constant has been used to derive thermodynamic parameters. 
ER  -

