Evaluation of hydrogen bonds in hydrobenzothiazoles 2-pyridin substituted.

In this work, the study of hydrogen bonds in the hydrobenzothiazoles 2-pyridin substituted of general formula {(C6H4CSNH)(C5H4N)R} [(1), R = H; (2), R = C6H5; (3), R = C5H4N] in solution and solid state by NMR, infrared and X-ray diffraction is described, Figure 1. On the one hand, for 2 and 3, the 1H NMR data in CDCl3 solution displayed the predominance of an intramolecular hydrogen bonding NH???N that is formed between the hydrogen atom of the NH group with the pyridinic nitrogen atom forming a five-membered ring. On the other hand, the 1H NMR spectra of 1 ? 3 in DMSO-d6 solution showed the formation of intermolecular hydrogen bonds of type NH???OS(CH3)2. In solid state, the NH???N intramolecular hydrogen bonding for 1 ? 3 by infrared and X-ray diffraction has been also established.