Gas phase chemistry of sulfonate anions: Basicities and fragmentation reactions

Abstract

The gas phase relative acidities of 15 sulfonic acids, RSO3H, have been determine via Cooks' kinetic method. The following acidity scale was established (starting with the weakest acid): methane sulfonic acid < ethane sulfonic acid < methoxy sulfonic acid < sulfuric acid < m-aminobenzene sulfonic acid ≈ p-aminobenzene sulfonic acids < p-toluene sulfonic acid < benzene sulfonic acid o-aminobenzene sulfonic acid < 5-sulfosalicylic acid < o-nitrobenzene sulfonic acid < cysteic acid < m-aminobenzene sulfonic acid < p-nitrobenzene sulfonic acid < triflic acid. In addition the gas phase fragmentation reactions of the conjugate bases, the sulfonate anions RSO3-, have been studied using MS/MS techni..