Synthesis, Structure, and Features of Anilinium Anilinomethanesulfonates

Two series of anilinomethanesulfonate derivatives, the anilinium and p-toluidinium anilinomethanesulfonates, were synthesized. They present interesting spectroscopic features and can be used as characteristic derivatives of the parent compounds. These series allow the easy study of the N-H stretching frequencies of the secondary amine whereas difficulties are encountered with the parent compounds due to the occurrence of O-H stretching bands in the same frequency range. All three compounds present a common fragmentation pattern in mass spectral analysis. Through these analyses, the salt structure of the anilinium anilinomethanesulfonates is demonstrated in opposition to a sulfonamide structure, giving further support to the salt structure of other series previously reported.