Synthesis, crystal structure, vibrational spectral and density functional studies of 4-(2,5-dioxo-2H-pyrrol-1(5H)-yl)antipyrine

The 4-(2,5-dioxo-2H-pyrrol-1(5H)-yl)antipyrine, C15H13N3O3, was synthesized by the condensation reaction of 4-aminoantipyrine and cis-butenedioic anhydride in toluene solution using triethylamine as catalyst, and characterized by X-ray diffraction and spectral techniques with density functional calculations. The experimental vibrational spectral bands were identified precisely with the aid of the theoretical vibrational modes, and the thermodynamic properties were also obtained by the theoretical frequencies. The total static dipole moment, polarizability and first-order hyperpolarizability obtained by B3LYP/6-31G(d) method are of 1.6896 Debye, 26.6464 Å3 and 7.8445 × 10−31 cm5/esu, respectively. The NBO analysis result reveals that the molecule has long-range electron-transfer characteristics with external perturbations, and presents a long-range electron transfer property with the energy gap of 3.895 eV. The frontier molecular orbitals should be responsible for the nonlinear optical and electron-transfer properties. The results indicate that the investigated compound might be an excellent photo-responsive material candidate.