Isoxazole derivatives of alpha-pinene isomers: Synthesis, crystal structure, spectroscopic characterization (FT-IR/NMR/GC-MS) and DFT studies

ERYILMAZ S., GÜL M., İNKAYA E., Taş M.

JOURNAL OF MOLECULAR STRUCTURE, cilt.1108, ss.209-222, 2016 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1108
  • Basım Tarihi: 2016
  • Doi Numarası: 10.1016/j.molstruc.2015.11.079
  • Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.209-222
  • Anahtar Kelimeler: 1,3-Dipolar cycloaddition reaction, ( plus or -)Alpha-pinene, Isoxazole derivatives, X-ray analysis, Density Functional Theory (DFT), DENSITY-FUNCTIONAL THERMOCHEMISTRY, 1,3-DIPOLAR CYCLOADDITION, MOLECULAR-STRUCTURE, PERTURBATION-THEORY, POPULATION ANALYSIS, SOFT ACIDS, NMR, NBO, RAMAN, NLO
  • Ondokuz Mayıs Üniversitesi Adresli: Evet

Özet

In this paper, the alpha-pinene isoxazole derivatives (3a-b-c, 4a-b) were synthesized via 1,3-dipolar cycloaddition and characterized with FT-IR, H-1 NMR, C-13 NMR and GC MS. Isoxazole (C21H23NO) compound (4a) 6,6,7a,-trimethyl-3-(naphthalen-2-yl)-3a,4,5,6,7,7a-hexahydro-5,7-methanobenzo[d] was characterized by X-ray single crystal diffraction technique. The compound crystallizes in the monoclinic space group P 2(1)2(1)2(1), with Z = 4. The molecular geometry of the compound was optimized by applying Density Functional Theory (DFT/B3LYP) method with 6-31G(d,p) and 6-311 + G(d,p) basis sets in the ground state and geometric parameters were compared with the X-ray analysis results of the structure. Results of the experimental FT-IR and NMR spectral analysis were examined in order to determine the compliance with vibrational frequencies, H-1 NMR and C-13 NMR chemical shifts values by using the Gauge-Independent Atomic Orbital (GIAO) method calculated over the optimized structure. Besides molecular electrostatic potential (MEP), frontier molecular orbitals (FMOs), some global reactivity descriptors, thermodynamic properties, non-linear optical (NLO) behaviour and Mulliken charge analysis of the (4a) compound were computed with the same method in gas phase, theoretically. (C) 2015 Elsevier B.V. All rights reserved.