R. Kant, B. Maiti, S. Awasthi
Jul 16, 2014
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Influential Citations
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Journal
Journal of Chemical Crystallography
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 C11(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 C11(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.Graphical AbstractThe crystal structure of compound 1, formed four motifs which are giving first-level graph set N1: C11(8)S(6)S(6)S(6) while compound 2, formed three motifs, giving first-level graph set N1: C11(8)C11(12)S(5) and second-level graph set N2(a,b): C22(14). Crystallographic and vibrational (IR) data were compared with the results of density functional theory (DFT) method at the B3LYP/6-31G(d,p) level and electronic (UV–vis) spectra was calculated by using the TD-DFT method.