The role of anionic, imidic and amidic forms in structure-activity relationships. Conjugation and bacteriostatic...

The electronic structures of anionic, imidic and amidic forms of sulphonamides were investigated and compared by means of I.R., Raman and U.V. spectroscopy. Indices reflecting the electronic situation of the common moiety p-H2N-C6H4-SO2 was a whole, although not necessarily related, physically, to any event taking place in the biological processes, were found to correlate with the in vitro bacteriostatic activity of the specific individual forms. The influence of N1-substituents both on the SO2 electronic features and on the coupling between the para amino group and the phenyl ring was discussed. It resulted that the most active chemical species, in this class of compounds, are characterized, electronically, by the most electron-rich common moiety and, in particular, by the most negative oxygens in the SO2 group and the most available (less engaged) lone-pair in the rho-amino group. These conclusions give a new settlement both to the problem of resonance and to the relation between resonance effects and bacteriostatic activity in this class of compounds.