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

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, 1H NMR, 13C 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 charac...

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Bibliographic Details
Published in:	Journal of molecular structure Vol. 1108; pp. 209 - 222
Main Authors:	Eryilmaz, Serpil, Guel, Melek, Inkaya, Ersin, Tas, Murat
Format:	Journal Article
Language:	English
Published:	Elsevier B.V 15-03-2016
Subjects:	(+ or −)Alpha-pinene 1,3-Dipolar cycloaddition reaction Atomic structure Cycloaddition Density Functional Theory (DFT) Derivatives Isoxazole derivatives Molecular structure Nuclear magnetic resonance Orbitals Phase shift X-ray analysis X-rays (+ or −)Alpha-pinene X-ray analysis 1,3-Dipolar cycloaddition reaction Isoxazole derivatives Density Functional Theory (DFT)
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Summary:	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, 1H NMR, 13C 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 212121, 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, 1H NMR and 13C 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. [Display omitted] •The alpha-pinene isoxazole derivatives were synthesized via 1,3-dipolar cycloaddition.•The compound was characterized with FT-IR, 1H NMR, 13C NMR, GC–MS and X-ray single crystal diffraction.•Density Functional Theory (DFT) method with 6-31G(d,p) and 6-311 + G(d,p) base sets were used for theoretical studies.•Molecular electrostatic potential (MEP), frontier molecular orbitals (FMOs) analysis were done.•Non-linear optical (NLO) properties were examined.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0022-2860 1872-8014
DOI:	10.1016/j.molstruc.2015.11.079