Structural study of benzidamine salicylate in the solid state and in solution

The vibrational (IR and Raman) and 1H and 13C NMR spectra of the analgesic and anti-inflammatory benzidamine salicylate (Benzasal) have been examined, and the results are described. The crystal structure of this compound has been determined by X-ray diffraction. To assist in interpretation of the spectroscopic data, some measurements of benzidamine, benzidamine hydrochloride, and salicylic acid have also been made. The most important intermolecular interactions of benzidamine salicylate in the solid state are N(+)H...O(-)...-C hydrogen bonds involving both salicylate oxygen atoms (d = 2.658 A and 3.228 A). At least the stronger hydrogen bond remains in CDCl3 solution. Moreover, the strong intramolecular hydrogen bond O-H...O(-)...-C within the salicylate anion has also been observed in the solid state and in solution.