Synthesis, Spectral Properties, Crystal Structure and DFT Studies of 2,2'-diamino-4,4'-(propane-2,2'-diyl)-Diphenol

A bisphenol-A derivative, 2,2′-diamino-4,4′-(propane-2,2-diyl)-diphenol (3), was synthesized by nitration of bisphenol-A and then by its reduction. The title compound was characterized by elemental analysis, typical spectroscopic techniques, namely FT-IR, 1H-NMR, and 13C-NMR. The structure of the compound was also determined by single crystal X-ray diffraction method. The compound crystallized in the orthorhombic system with space group Pbcn and a = 15.51106(18) Å, b = 11.6910 (10) Å, c = 7.6473 (7) Å. It is seen that the hydrogen atoms of the -OH groups are in trans-position to the NH2 groups in the crystal structure of the title compound. Moreover, it was observed in the dimeric lattice that the hydrogens of the –NH2 groups made intramolecular and those of the –OH groups intermolecular hydrogen bonds. The geometry of the compound was optimized by the DFT method and the results were compared with the X-ray diffraction data. Frontier molecular orbitals of the title compound were calculated by using the B3LYP/6-31G(d) method. MEP analysis and Mulliken charge density, Global reactivity and thermodynamic properties were also performed.