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A new 2-hydroxy-1-naphthaldehyde Schiff base derived nickel(II) complex ( 4 ) was synthesized and fully characterized. Analysis of the structure of  4  by single-crystal X-ray diffraction shows two chelating Schiff base ligands bound to nickel in a  trans  [O ∧ N(Ni 2+ )N ∧ O] fashion. Hence, in a molecule of  4 , two ligands are four coordinate to a Ni(II) center through the imine nitrogen and naphthyloxyl oxygen atoms. This coordination mode resulted in a square planar complex that is stabilized in the solid-state by a network of intermolecular O-H···N hydrogen bonds between neighboring molecules. The  1 H NMR data showed the loss of the hydroxyl (O H ) proton signal and an upfield shift of the metal-bound imine (-N H ) proton signal, while the IR data also showed a lower energy shift in the absorption frequency of the imine ( C = N ) bond due to back donation from the coordinated Ni(II) center. As a catalyst for the transfer hydrogenation of a range of ketones,  4  showed good catalytic activity at a very low concentration of 0.1 mol% with 2-propanol as the model substrate. The catalyst is also effective for various related ketone substrates bearing a range of steric and electronic regulating groups.

Structural characterization of a square planar Ni(II) complex and its application as a catalyst for the transfer hydrogenation of ketones