Combined experimental and theoretical approaches to the molecular structure of 4-(1-formylnaphthalen-2-yloxy)phthalonitrile.

The novel compound 4-(1-formylnaphthalen-2-yloxy)phthalonitrile, C(19)H(10)N(2)O(2,) has been synthesized and characterized by IR, UV-vis, NMR and X-ray single-crystal determination. The title compound, is built up from two planar groups (naphthalen and phthalonitrile), with a dihedral angle of 64.10(4)° between them. The crystal structure is stabilized by weak C-H···O hydrogen-bond and π-π interactions. The structural and spectroscopic data of the compound in the ground state have been calculated using density functional theory (DFT) and Hartree-Fock (HF) with the 6-31G(d,p) basis set. The vibrational study was interpreted in terms of potential energy distribution (PED). The observed wave number in FT-IR spectra was analyzed and assigned to different normal modes of the molecule. Using the TD-DFT and TD-HF methods, electronic absorption spectra of the title compound were predicted and good agreement with the TD-DFT method and the experimental determination was found. Isotropic chemical shifts ((13)C and (1)H NMR) were calculated using the gauge-invariant atomic orbital (GIAO) method. The HOMO and LUMO analyses were used to elucidate information regarding charge transfer within the molecule.