TY - JOUR
T1 - Hydrolysis of aryl N-methylaminosulphonates
T2 - Evidence consistent with an E1cB mechanism
AU - Williams, Andrew
AU - Douglas, Kenneth T.
PY - 1974
Y1 - 1974
N2 - The following evidence is consistent with an E1cB mechanism for the hydrolysis of aryl N-methylaminosulphonates: (1) rate constants for the hydrolysis of the title esters are independent of pH in the alkaline region and obey a Broønsted type relationship with a β1.g, -1.8; (2) the 4-nitrophenyl N-methylamino-ester shows a 108-fold greater reactivity to hydroxide ion than does the corresponding dimethylamino-ester; and (3) increasing the concentration of amine buffer has no effect on the rate constant for the release of 4-nitrophenol from the monomethyl ester but at 1M-amine concentration all the product is in the form of the sulphonamide.
AB - The following evidence is consistent with an E1cB mechanism for the hydrolysis of aryl N-methylaminosulphonates: (1) rate constants for the hydrolysis of the title esters are independent of pH in the alkaline region and obey a Broønsted type relationship with a β1.g, -1.8; (2) the 4-nitrophenyl N-methylamino-ester shows a 108-fold greater reactivity to hydroxide ion than does the corresponding dimethylamino-ester; and (3) increasing the concentration of amine buffer has no effect on the rate constant for the release of 4-nitrophenol from the monomethyl ester but at 1M-amine concentration all the product is in the form of the sulphonamide.
UR - https://www.scopus.com/pages/publications/37049130332
U2 - 10.1039/p29740001727
DO - 10.1039/p29740001727
M3 - Article
AN - SCOPUS:37049130332
SN - 1472-779X
SP - 1727
EP - 1732
JO - Journal of the Chemical Society, Perkin Transactions 2
JF - Journal of the Chemical Society, Perkin Transactions 2
IS - 14
ER -