Hydrogen bonding patterns and DFT studies of (4-Acetylphenyl)amino 2,2-Dimethylpropanoate and (E)-1-(4-aminophenyl)-3-[4-(dimethylamino)phenyl] prop-2-en-1-one

Abstract

The (4-acetylphenyl)amino 2,2-dimethylpropanoate (1) and (E)-1-(4-aminophenyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one (2), were synthesized and characterized by elemental analysis, FT-IR, 1H NMR, 13CNMR and single crystal X-ray diffraction techniques. Both compounds 1 and 2 crystallized in orthorhombic crystal system with Pbca and P212121 space group respectively, having the unit cell parameters: a = 11.7220(12) Å, b = 14.4580(13) Å, c = 15.7853(12) Å, β = 90°, Volume = 2675.2(4) Å3, Z = 8 for 1 and a = 6.1146(5) Å, b = 9.0567(8) Å, c = 26.079(3) Å, β = 90°, Volume = 1444.2(2) Å3, Z = 4 for compound 2. The crystal structures of both compounds (1 and 2) are stabilized by N-H···O strong intermolecular hydrogen bonding forming C 1 1 (8) motifs. In compound 1, the molecules are linked by three C-H···O intramolecular H-bond forming S(6) motifs. In compound 2, the molecules are linked by C-H···N intermolecular H-bond exhibiting C 1 1 (12) motif and C-H···O intramolecular H-bond leading to S(5) motif. Crystallographic and vibrational data are compared with the results of density functional theory (DFT) method at the B3LYP/6-31G(d,p) level. The electronic (UV-vis) spectra was calculated by using the TD-DFT method and correlated with experimental spectra. © 2014 Springer Science+Business Media New York.