67065-64-9Relevant articles and documents
KINETICS OF THE REACTION OF IMIDAZOLE WITH S-p-NITROPHENYL THIOACETATE IN APROTIC SOLVENTS
Dadali, V. A.,Panchenko, B. V.,Litvinenko, L. M.
, p. 1470 - 1477 (2007/10/02)
The kinetics of the reversible reaction of S-p-nitrophenyl thioacetate with imidazole and some of its derivatives in benzene and acetonitrile were investigated.In the low-polarity solvent not only the monomeric forms of imidazole but also its hydrogen-bonded associates take part in the reaction, whereas in acetonitrile only the monomers of imidazole react.The highly polar acetonitrile leads to an increase in the rate of both the forward and the reverse reaction (by 35 and 180 times, respectively).The equilibrium constant for the reaction of p-nitrophenyl thioacetate with imidazole is 1.9 in benzene and 0.39 in acetonitrile.Comparison of the reactivity of imidazole and its N-methyl analog showed that in acetonitrile the reaction occurs without proton transfer, whereas in benzene such transfer is realized in the rate-determining stage.