The nature of the products of deprotonation of disulfonyl carbon acids in acetonitrile solvent

The series of bis(ethylsulfonyl) and bis(benzylsulfonyl) activated carbon acids were synthesized and the products of the deprotonation of these carbon acids by strong, organic, cyclic bases such as: 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) and 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD) in acetonitrile were characterized by conductance measurements. The values of pKa in acetonitrile are in the range between 19.1 and 24.23 for disulfonyl carbon acids and 25.96 and 25.0 for TBD and MTBD appropriately. The conductometric titration of 0.001 M carbon acids solution in acetonitrile with 0.1 M TBD or 0.1 M MTBD in acetonitrile has been carried out. The dissociation constant values of the products of the reaction between studied carbon acids and TBD and MTBD bases in acetonitrile at 25 °C have been estimated. The results of the conductometric study for various disulfonyl carbon acids indicate convincingly that the products of the studied proton transfer reactions in acetonitrile occur as free ions or can exist also in the form of ion pairs in case of phenyl[bis(ethylsulfonyl)]methane.