Crystallography and DFT Studies of Synthesized Tetraketones


  • Elma Veljović
  • Krešimir Molčanov
  • Mirsada Salihović
  • Una Glamočlija
  • Amar Osmanović University of Sarajevo, Faculty of Pharmacy
  • Nevzeta Ljubijankić
  • Selma Špirtović-Halilović



Tetraketones, X-ray diffraction, DFT, HOMO-LUMO energies


Two tetraketone derivatives, one previously reported and one novel, were synthesized, whose structures have been confirmed by elemental analyses, NMR, HPLC-MS, and IR spectroscopy. The crystal structures of synthesized tetraketones were determined using X-ray single-crystal diffraction. To analyze the molecular geometry and compare with experimentally obtained X-ray crystal data of synthesized compounds 1 (2,2'-((4-nitrophenyl)methylene)bis(5,5-dimethylcyclohexane-1,3-dione)) and 2 (2,2'-((4-hydroxy-3-methoxy-5-nitrophenyl)methylene)bis(5,5-dimethylcyclohexane-1,3-dione)), DFT calculations were performed with the standard 6-31G*(d), 6-31G**, and 6-31+G* basis sets. The calculated HOMO-LUMO energy gap for compound 1 was 4.60 eV and this value indicated that compound 1 is chemically more stable compared to compound 2 whose energy gap was 3.73 eV. Both compounds' calculated bond lengths and bond angles were in very good accordance to experimental values determined by X-ray single-crystal diffraction.





Organic chemistry