87962-96-7Relevant articles and documents
Electrophilic Catalysis of Sulphate (-SO3-) Group Transfer: Hydrolysis of Salicyl Sulphates assisted by Intramolecular Hydrogen Bonding
Hopkins, Andrew Ramsay,Green, Adam Llywellyn,Williams, Andrew
, p. 1279 - 1284 (2007/10/02)
The hydrolysis of substituted salicyl sulphates has been measured over a range of pH values at 70 deg C to obtain kinetic parameters for hydronium ion (kH) and carboxylic acid (kp) calalysis.A Jaffe treatment of the carboxy-catalysis parameter for a range of nuclear substituents yields ρphenol 1.51; ρcarboxy 0 indicates that the carboxy-function does not ionise on going from the ground- to the transition-state, consistent with hydrogen bonding rather than catalysis through proton transfer.The change in 'effective' charge on the phenol oxygen on going from the ground- to the transition-state confirms less build up of negative charge than in the uncatalysed hydrolysis of aryl sulphates.