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

Tereci H., ASKEROĞLU İ., AKDEMİR N., Ucar I., Buyukgungor O.

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, vol.96, pp.569-577, 2012 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 96
  • Publication Date: 2012
  • Doi Number: 10.1016/j.saa.2012.07.005
  • Journal Name: SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.569-577
  • Keywords: Phthalonitrile, X-ray diffraction, FT-IR, C-13 and H-1 NMR, UV-Vis, DFT, DENSITY-FUNCTIONAL THEORY, VIBRATIONAL-SPECTRA, DFT CALCULATIONS
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

The novel compound 4-(1-formylnaphthalen-2-yloxy)phthalonitrile, C19H10N2O2, 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)degrees between them. The crystal structure is stabilized by weak C-H center dot center dot center dot O hydrogen-bond and pi-pi 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 (C-13 and H-1 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. (c) 2012 Elsevier B.V. All rights reserved.