Synthesis, characterization, crystal structures, Hirshfeld surface analysis and DFT computational studies of new Schiff Bases derived from Phenylhydrazine

Abstract

In this research, four novel ligands were synthesized from hydrazine derivatives. The hydrazine compounds via reacting 2, 4-dinitrophenylhydrazine with 2-hydroxy-4-methoxybenzaldehyde (HL1), 2-hydroxy- 5-bromobenzaldehyde (HL2), 2-hydroxy-naphtaldehyde (HL3) and 4-nitrophenylhydrazine with 2-hydroxy-4-methoxybenzaldehyde (HL4) were synthesized, characterized using FT-IR, Raman and UV–Vis spectrum and it structure were confirmed by X-ray diffraction studies. Novel compounds were recovered to crystallize the systems in monoclinic, orthorhombic, triclinic and monoclinic, crystal structures with P21/n, Pbcn, P-1, and P21/c space groups in ligands (HL1), (HL2), (HL3) and (HL4), respectively. Afterwards, the present study compared the experimental parameters in the UV–Vis and FT-IR spectra with the theoretical values.The results showed that at B3LYP/6-311 + G (d, p) level, DFT was able to properly reproduce the structure of the title ligands. Moreover, Hirshfeld surface (HS) analyses, particularly dnorm surface and FPs (fingerprint plots), were employed to decode intermolecular interactions in the crystal system and contribution of component units in the construction of the 3D architecture. These examinations presented the general description of such inter-contact interactions by means of an attractive graphical approach by 3D Hirshfeld surfaces and 2D fingerprint plots derived from the surfaces. Hirshfeld surface analysis indicated the dominant role of various hydrogen intermolecular interactions such as H⋯H, C⋯H/H⋯C and O⋯H/H⋯O for all compounds and H⋯Br contacts for the HL2 (because of the) into the crystal packing which are discussed.