NEGATIVE-ION, CHEMICAL-IONIZATION MASS-SPECTROMETRY OF SULFONIC-ACID ESTERS OF CARBOHYDRATES

Negative-ion, chemical-ionization mass spectra of p-toluenesulfonates 1-6, 2-naphthalenesulfonates 7-10, and p-nitrobenzenesulfonate 11 show that these compounds readily form radical anions in the gas phase. Re gardless of the structure of the carbohydrate portion of the molecule, tosylate radical anions fragment by cleavage of the sulfur-carbon bon d. Changes in the sulfonic acid portion of the molecule open new react ion pathways. The radical anions derived from compounds 7-10 break car bon-oxygen and sulfur-oxygen bonds in addition to the sulfur-carbon bo nd cleavage observed for p-toluenesulfonates.