Synthesis, crystal structure, vibrational spectral and density functional studies of 4-(1,3-dioxoisoindolin-2-yl)antipyrine

The 4-(1,3-dioxoisoindolin-2-yl)antipyrine, C19H15N3O3, was synthesized by the condensation reaction of 4-aminoantipyrine and phthalic anhydride in ethanol solution using triethylamine as catalyst, and characterized by X-ray diffraction and spectral techniques. The experimental spectral bands were structurally assigned with the theoretical calculation, and the thermodynamic properties of the studied compound were obtained from the theoretically calculated frequencies. The linear polarizability (α0) and first hyperpolarizabilities (β0) calculated at B3LYP/6-31G(d) level are of 33.6921 Å3 and 2.7835 × 10−30 cm5/esu, respectively. The NBO analysis reveals that the studied molecule presents a structural characteristic of long-range electron-transfer with the energy gap of ⩾3.639 eV. The frontier molecular orbitals are responsible for the electron polarization and long-range electron-transfer properties. The results indicate that the compound might be an excellent candidate of photo-responsive materials.

► The title compound was synthesized in one step by an amine-anhydride reaction.
► The molecule form effective dihedral angles between three conjugated moieties.
► The vibrational spectra have been precisely ascribed to the molecular structure.
► The thermodynamic properties are obtained by the theoretical vibrational analysis.
► The theoretical first-order hyperpolarizabilitie is seven times magnitude of urea.
► The studied molecule presents LRET of ⩾3.639 eV obtained by NBO and FMO analysis.