Synthesis, spectroscopic and crystal structure studies of N,N'-Bis [2-hydroxy-3-methoxybenzylidene] diaminobenzene derivatives

The reaction of 0-vanillin 1 with phenylenediamine isomers 2-4 in dichloromethane formed three diaminobenzene derivatives: N,N'-bis [2-hydroxy-3-methoxybenzylidene]-1,2-diaminobenzene 5, N,N'-bis [2-hydroxy-3-methoxybenzylid-ene]-l,3-diaminobenzene 6 and N,N'-bis [2-hydroxy-3-methoxybenzylidene]-l,4-di-aminobenzene 7, respectively, All compounds were obtained as single crystals and the structures were determined by X-ray crystallography. All compounds were confirmed by FTIR, HRMS, ID and 2D NMR spectroscopy. The complete assignments of these compounds, using ID and 2D NMR including APT, DEPT-135, COSY, HMQC and HMBC in CDC1[3], will be discussed