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

Yıl 2016, Cilt: 17 Sayı: 4, 641 - 659, 01.12.2016

Serpil Eryılmaz Kerem Mesci Melek Gül Ersin İnkaya

https://doi.org/10.18038/aubtda.267054

Cited By: 1

Öz

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, ¹H-NMR, ¹³C-NMR,
UV-Vis and the single-crystal X-ray diffraction technique. The 3,7-bis(4-(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 (DFT/B3LYP) method with
6-311G(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 = 20.634(4) Å, b = 11.179(2) Å, c = 11.0690(17)
Å and Z = 4 unit cell parameters. Also,
the spectral results were examined with calculated vibrational frequencies, ¹H-NMR, ¹³C-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 6-311G(d,p) basis set using the Conductor Polarizable
Continuum Model (CPCM). The frontier molecular orbitals (FMOs), molecular
electrostatic potential (MEP) and electronic structure parameters (dipole
moment, electronegativity, chemical hardness-softness, ionization potential,
electron affinity, etc.) were examined to get information about the chemical
stability of the structure. 

Anahtar Kelimeler

Bisisoxaoline, DFT, Single Crystal X-ray, FT-IR

Kaynakça

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