7134-11-4Relevant articles and documents
Structure-reactivity correlations in the dissociative hydrolysis of 2′,4′-dinitrophenyl 4-hydroxy-X-benzenesulfonates
Cevasco, Giorgio,Thea, Sergio
, p. 6814 - 6817 (2007/10/03)
The hydrolysis reactions of several title esters in water at 60°C follow the rate law kobs = (ka + kb[OH-])/(1 + αH/Ka), where Ka is the ionization constant of the hydroxy group of the ester and kb is the second-order rate constant for the SN2(S) attack of hydroxide ion on the ionized ester. Hammett and Br?nsted correlations are consistent with a previous proposal that the mechanism related to ka is dissociative. An unusual relationship between ka values and redox equilibrium constants for substituted quinones is found to hold: this finding further supports the dissociative nature of the pathway related to ka.
Sulfonation and sulfation on reaction of 1,2-dihydroxybenzene and its methyl ethers in concentrated aqueous sulfuric acid
Cerfontain, Hans,Coenjaarts, Norbert J.,Koeberg-Telder, Ankie
, p. 325 - 330 (2007/10/02)
The homogeneous sulfonation of 1,2-dihydroxybenzene (1), its monomethyl (2) and dimethyl ether (3) in concentrated aqueous sulfuric acid at 25 deg C has been studied and isomer distributions, as well as rate coefficients for the sulfonation of 1-3 and their monosulfonic acids, have been determined.In 73.5-87.5percent H2SO4, 1 yields the 3- and 4-sulfonic acids in a ratio of 25:75, 2 yields the 4-, 5- and 6-sulfonic acids in a ratio of 46:36:18 in 73.5percent H2SO4 and 50:39:11 in 87.5percent H2SO4, whereas 3 yields only the 4-sulfonic acid.The remarkable absence of the 3-sulfonic acid (87.5percent H2SO4, the 4-sulfonic acid of 1 and the 5-sulfonic acid of 2 are present in part in the form of their hydrogen sulfate.In that acid region, the 3- and 4-sulfonic acids of 1 both yield the 3,5-disulfonic acid, the 4- and 6-sulfonic acids of 2 both yield the 4,6-disulfonic acid and the 4-sulfonic acid of 3 mainly yields the 4,6- together with some 4,5-disulfonic acid.