Synthesis, structural, and spectral studies of N,N′-bis(5-methylsalicylidene)-2,2′-diamino-4-4′-di-(trifloromethyl)-diphenyl disulfide

A new disulfide compound N,N'-bis-(5-methylsalicylidene)-2,2'-diamino-4-4'-di-(trifloromethyl)diphenyl disulfide (C30H22F6N2O2S2) was prepared and characterized by H-1-NMR, IR, mass spectroscopy, and single-crystal X-ray diffraction. Spectroscopic assignments and the crystallographic results indicate the predominance of the phenol-imine tautomeric form. [For example, N=C double bonds 1.274(9)angstrom and 1.275(9)angstrom, two very close hydrogen peaks to the atomic positions of O atoms in difference Fourier map and two strong intramolecular hydrogen bonds (O-H center dot center dot center dot N) with O center dot center dot center dot N distances of 2.611(10) and 2. 613(8) angstrom strongly indicate that this tautomeric form is preferred]. The strong effect of the para CF3 groups in the molecular and crystallographic arrangement was attributed to the electronegativity of the CF3 groups.