3233-60-1Relevant articles and documents
Ground state structures of sulfate monoesters and sulfamates reveal similar reaction coordinates for sulfuryl and sulfamyl transfer
Denehy, Emma,White, Jonathan M.,Williams, Spencer J.
, p. 314 - 316 (2006)
Structure/reactivity and structure/structure correlations of 5 sulfate monoesters and 11 sulfamate esters determined by low temperature X-ray crystallography reveal similar ground state deformations that suggest similar reaction coordinates for sulfuryl and sulfamyl group transfer. The Royal Society of Chemistry 2006.
Sulfonation and sulfation on reaction of 1,4-dihydroxybenzene and its methyl ethers in concentrated sulfuric acid
Cerfontain, Hans,Koeberg-Telder, Ankie
, p. 583 - 591 (2007/10/02)
The homogeneous reactions of 1,4-dihydroxybenzene (1), its monomethyl (2) and dimethyl ether (3) and 2-3-sulfonic acid in 68-105percent H2SO4 at 25 deg C have been studied and isomer distributions and rate coefficients for the various subsequent sulfonations, as well as the equilibrium data for the sulfation (-OH -OSO3H), are reported.For 2, the ratio of 2- to 3-sulfonation decreases upon increasing the sulfuric acid concentration from 68-98.5percent H2SO4, due to a gradual change-over in the effective sulfonating entity from H3SO4(1+) to H2S2O7.For 1-2-sulfonic acid (1-2-S), 2-2-S and 2-3-S, the ratios of 5- to 6-sulfonation are all ca. 25:75, whereas 3-2-S only yields the 5-sulfonic acid.Demethylation of the sulfonic acids of 2 and 3 in = 98.5percent H2SO4 is of minor importance, but plays a major role in 105,0 percent H2SO4, the eventual products being the bis(hydrogen sulfate)s 10 and 15, the tricyclic bis(sulfate sulfonate anhydride) 11 and the bicyclic hydrogen sulfate 16.Mechanisms for the sulfodemethylation and for the cyclization of the 2-sulfophenyl hydrogen sulfate moiety to the 1,3,2,4-benzodioxadithiin 2,2,4,4-tetraoxide system are proposed.
