Solvent effects on the infrared and 1h-nmr spectra of n, n'-thiodianilines

Abstract

The influence of various common basic solvents on the IR and 1H-NMR spectra of a series of N,N′-thiodianilines, , X = H, OMe, Br, Cl, and m-NO2 has been studied. The solvent shifts of both, frequencies θ(NH) and chemical shifts δ(NH), show a near linear dependence on solvent basicity, DN (DN: Donor Number). The sensitivity of the thiodianilines to the solvent, expressed as the slopes in the curves δ(NH) and θ(NH) vs. DN, are determined by the inductive effect of the substituents on the amino group. The anomalous behavior of the m-NO2 derivative is attributed to strong intermolecular interactions.