A density functional study for the molecular structure and chemical properties of 2-(N,N-dibenzoylamino)-3-pyridylbezoate Canan Kazak 1,* , Orhan Büyükgüngör 1 , Mustafa Odabaşoğlu 2 , Figen Arslan 3 , Cem Özdoğan 4 and Ziya B. Güvenç 5 *1 Department of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, TR-55139 Kurupelit Samsun, Turkey, 2 Department of Chemistry, Faculty of Arts and Sciences, Ondokuz Mayıs University, TR-55139 Kurupelit Samsun, Turkey, 3 Department of Chemistry, Faculty of Arts and Sciences, Karabük University, Karabük, Turkey, 4 Department of Computer Engineering, Çankaya University, Balgat 06530 Ankara, Turkey 5 Department of Electronic and Communication Engineering, Çankaya University, Balgat 06530 Ankara, Turkey Abstract The 2-amino-3- hydroxypyridine reacts with benzoil chloride to give 2-(N,N- dibenzoylamino)-3-pyridylbezoate (I). The compound has been studied by elemental analysis and X-ray crystallography and also its molecular orbital diagram has been calculated with the density functional theory (DFT) method. The molecules of (I) crystallize in the orthorhombic space group P2 1 2 1 2 1 and the crystal packing involves both hydrogen-bonding and C-H...π interactions (Fig.2.). 2-(N,N-dibenzoylamino)-3-pyridylbezoate molecule is investigated by solving the Kohn-Sham equations in the density functional theory framework with B3LYP/6- 311++G(d,p) level of theory. Geometry optimization, Natural Bond Orbital (NBO) analysis and vibration frequency calculations were performed. The calculated total energy with zero- point vibration energy correction is found as -38415.44 eV with the electronic state of 1 A. The calculated Highest Occupied Molecular Orbital - Lowest Unoccupied Molecular Orbital gap is 0.18295 eV. This small gap value shows that this system is chemically reactive. A delocalized and multi-centered π bonding nature of the chemical bonding is predicted from the molecular orbital pictures and Natural Bond Orbital analysis. The calculated first three * Corresponding author: Fax: +90 (362) 4576081; e-mail: ckazak@omu.edu.tr