Structure and spectroscopy of diorganotin(IV) complexes derived from N′-(2-hydroxy-3-methoxybenzylidene)benzohydrazide

Three new diorganotin(IV) complexes of the general formula R2Sn[3-(OMe)-2-OC6H3CHN–NC(O)Ph] (R = Ph, Ia; R = Me, Ib; R = n-Bu, Ic) have been synthesised from the corresponding diorganotin(IV) dichlorides and the ligand, N′-(2-hydroxy-3-methoxybenzylidene)benzohydrazide in methanol at room temperature in the presence of trimethylamine. All the complexes have been characterized by elemental analysis, IR and 1H, 13C, 15N, 119Sn NMR spectra, and their structures have been confirmed by single crystal X-ray diffraction analysis of one representative compound Ia. Complex Ia crystallises in the orthorhombic system, space group Pna21 with a = 12.424(5), b = 9.911(5), c = 18.872(5) Å; Z = 4. The ligand N′-(2-hydroxy-3-methoxybenzylidene)benzohydrazide (H2L) coordinates to the metal centre in the enolate form via the phenolic O, imino N and enolic O atoms. In Ia, the central tin atom adopts a distorted trigonal bipyramidal coordination geometry with the oxygen atoms in axial positions, while the imino nitrogen atom of the Schiff base and the two phenyl groups occupy the equatorial sites. The δ(119Sn) values for the complexes Ia, Ib and Ic are −327.3, −151.7 and −187.2 ppm, respectively, thus indicating penta-coordinated Sn centres in solution.

Graphical abstractThree new diorganotin(IV) complexes, having a distorted trigonal bipyramidal geometry, have been synthesised from the corresponding diorganotin(IV) dichlorides and the ligand, N′-(2-hydroxy-3-methoxybenzylidene)benzohydrazide, in methanol.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Synthesis of diorganotin(IV) complexes at room temperature. ► The tridentate nature of the ligand is confirmed. ► Both NMR spectra and X-ray structure indicate same coordination geometry.