TY - JOUR
AU - Raftery, William V.
AB - Aryl esters of 4-hydroxybutyric acid, 5-hydroxyvaleric acid, 2-hydroxyphenylacetic acid, and 3-(2-hydroxyphenyl)propionic acid are lactonised in reactions whose rates are proportional to 10. The anchimeric assistance corresponds to rate enhancements of 10–10 over the rates of hydrolysis of analogous esters without the hydroxy-groups. The reaction of phenyl 4-hydroxybutyrate shows buffer catalysis, possibly general base catalysis, in acetate and phosphate buffers. The esters of 4-hydroxybutyric acid and 5-hydroxyvaleric acid also react with participation by the hydroxy-groups in the acid-catalysed hydrolysis but those of 2-hydroxyphenylacetic acid and 3-(2-hydroxyphenyl)propionic acid do not. The rate of hydrolysis of phenyl 4-hydroxybutyrate increases more rapidly with acid concentration than that of phenyl butyrate does. The  values are 0·59 and 0·99 respectively. The hydrolyses of the lactones of 2-hydroxyphenylacetic acid and 3-(2-hydroxyphenyl)propionic acid were also studied.
TI - Hydroxy-group participation in ester hydrolysis
JO - Journal of the Chemical Society, Perkin Transactions 2
DO - 10.1039/p29730001118
DA - 1973-01-01
UR - https://www.deepdyve.com/lp/royal-society-of-chemistry/hydroxy-group-participation-in-ester-hydrolysis-wQMEAyuKBM
SP - 1118
EP - 1125
VL - 
IS - 8
DP - DeepDyve
ER -