An experimental and theoretical investigation of the molecular and electronic structure of 2-amino-4-chloro-6-pyrazolyl-[1,3,5]triazine, forming supramolecular linear tapes in solid state

The new derivative 2-amino-4-chloro-6-pyrazolyl-[1,3,5]triazine, 1, prepared by reaction of 2-amino-4,6-dichloro-[1,3,5]triazine with an excess of pyrazole, has been characterized by 1H, 13C and 15N NMR measurements and single crystal XRD structural determination. The non-equivalence of the NH2 hydrogens evidences the iminium character of this moiety. Compound 1, exploiting strong H-bonds, self-assembles generating supramolecular linear tapes. Theoretical calculations are in good agreement with experimental solid state and solution data. Electronic properties of1 (lowest lying excitation energies and corresponding oscillator strength) have also been determined by time dependent DFT at the PBE level.