Synthesis, crystal structure analysis, spectral characterization, quantum chemical calculations, antioxidant and antimicrobial activity of 3-(4-chlorophenyl)-3a,4,7,7a-tetrahydro-4,7-methanobenzo[d]isoxazole

ERYILMAZ S., GÜL M., İNKAYA E., İDİL Ö., Özdemir N.

JOURNAL OF MOLECULAR STRUCTURE, cilt.1122, ss.219-233, 2016 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1122
  • Basım Tarihi: 2016
  • Doi Numarası: 10.1016/j.molstruc.2016.05.081
  • Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.219-233
  • Anahtar Kelimeler: Isoxazole, X-ray analysis, Density Functional Theory (DFT), Quantum chemical calculations, Antioxidant-antimicrobial activities, X-RAY-STRUCTURE, NONLINEAR-OPTICAL PROPERTIES, DENSITY-FUNCTIONAL THERMOCHEMISTRY, SPECTROSCOPIC CHARACTERIZATION, FT-IR, AB-INITIO, VIBRATIONAL-SPECTRA, MOLECULAR-STRUCTURE, PERTURBATION-THEORY, SOFT ACIDS
  • Ondokuz Mayıs Üniversitesi Adresli: Evet

Özet

In this paper, 3-(4-chlorophenyl)-3a,4,7,7a-tetrahydro-4,7-methanobenzo[d]isoxazole was synthesized via 1,3 dipolar cycloaddition, characterized by spectroscopic analysis such as FT-IR, H-1 NMR, C-13 NMR, UV-Vis, LC-MS/MS, Elemental Analysis, and X-ray Single Crystal diffraction technique. The Density Functional Theory (DFT/B3LYP) method with 6-311G(d,p) basis set in the ground state was applied for quantum chemical calculations and molecular geometric parameters of the compound were compared with the X-ray analysis results. FT-IR, NMR and UV Vis spectral analysis were analysed to determine the compliance with the vibrational frequencies, H-1 NMR and C-13 NMR chemical shifts and absorption wavelength values. The frontier molecular orbitals (FMOs), some global reactivity descriptors, molecular electrostatic potential (MEP), thermodynamic properties, non-linear optical (NLO) behaviour of the compound were examined with the same method in gas phase, theoretically. Moreover, antioxidant activity was determined with three different methods - DPPH radical scavenging, reducing and metal chelating, antimicrobial activity were carried out with Gram positive, Gram negative and Eukaryote for the title compound. (C) 2016 Elsevier B.V. All rights reserved.