THE INVESTIGATION OF SPECTROSCOPIC AND THEORETICAL METHODS OF BISISOXAOLINE DERIVATIVE OF NORBORNADIEN

Authors : Serpil ERYILMAZ, Kerem MESCİ, Melek GÜL, Ersin İNKAYA

Pages : 641-659

Doi:10.18038/aubtda.267054

View : 18 | Download : 7

Publication Date : 2016-12-01

Article Type : Research Paper

Abstract :In this study, the synthesis of bisisoxaoline derivative of norbornadien from heterocyclic compounds was performed via 1,3-dipolar cycloaddition reaction, the structural properties of derivative characterized by spectroscopic analysis such as FT-IR, 1 H-NMR, 13 C-NMR, UV-Vis and the single-crystal X-ray diffraction technique. The 3,7-bisinsert ignore into journalissuearticles values(4-insert ignore into journalissuearticles values(tert-butyl);phenyl);-3a,4,4a,7a,8,8a-hexahydro-4,8-methanobenzo[1,2-d:4,5-d’]diisoxazole compound was optimized using Density Functional Theory insert ignore into journalissuearticles values(DFT/B3LYP); method with 6-311Ginsert ignore into journalissuearticles values(d,p); basis set in the ground state and the geometric parameters compared with single-crystal X-ray diffraction technique. The compound crystallizes in the monoclinic space group C2/c with a = 20.634insert ignore into journalissuearticles values(4); Å, b = 11.179insert ignore into journalissuearticles values(2); Å, c = 11.0690insert ignore into journalissuearticles values(17); Å and Z = 4 unit cell parameters. Also, the spectral results were examined with calculated vibrational frequencies, 1 H-NMR,  13 C-NMR chemical shift values and absorption wavelengths, theoretically. The energetic behaviour of the compound in different solvent media was examined with TD-DFT/B3LYP method and 6-311Ginsert ignore into journalissuearticles values(d,p); basis set using the Conductor Polarizable Continuum Model insert ignore into journalissuearticles values(CPCM);. The frontier molecular orbitals insert ignore into journalissuearticles values(FMOs);, molecular electrostatic potential insert ignore into journalissuearticles values(MEP); and electronic structure parameters insert ignore into journalissuearticles values(dipole moment, electronegativity, chemical hardness-softness, ionization potential, electron affinity, etc.); were examined to get information about the chemical stability of the structure. 
Keywords : Bisisoxaoline, DFT, Single Crystal X ray, FT IR