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THE SPECTROSCOPIC ANALYSIS OF 2,4'-DIBROMOACETOPHENONE MOLECULEBY USING QUANTUM CHEMICAL CALCULATIONS

Yıl 2016, Cilt: 17 Sayı: 4, 677 - 702, 01.12.2016
https://doi.org/10.18038/aubtda.267115

Öz

A
spectroscopic investigation, used quantum chemical calculations, of
2,4'-dibromoacetophenone (2,4'-DBrA) molecule have been obtained in this paper.
The calculations were supported the experimental results by IR, 1H
and 13C NMR techniques. Geometrical parameters and optimized
energies of 2,4'-DBrA molecule were performed by density functional theory
(DFT) B3LYP method 6-311++G(d,p) basis sets. After the geometry optimization of
2,4'-DBrA the vibrational spectra were obtained for this structure. The
fundamental vibrations were assigned to base on potential energy distribution
(PED) of the vibrational modes by using VEDA 4 (Vibrational Energy Distribution
Analysis) program. Density of states for total (TDOS), partial (PDOS) and also
overlap population (OPDOS) analysis were obtained. 1H and 13C
NMR chemical shifts were recorded by using the gauge-invariant atomic orbital
(GIAO) method. Besides, electronic properties, such as HOMO and LUMO energies,
were performed by time-dependent density functional theory (TD-DFT). Also,
molecular electrostatic potential surface (MEPs) and thermodynamic properties
were calculated for title molecule. The results are showed consistent with the
obtained experimental results.

Kaynakça

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Yıl 2016, Cilt: 17 Sayı: 4, 677 - 702, 01.12.2016
https://doi.org/10.18038/aubtda.267115

Öz

Kaynakça

  • [1] Griffin, R.N., Phosphorescence of Aromatic Ketones in Low-Temperature Glasses, Photochemistry and Photobiology. (1968) 7 159–173.
  • [2] Lutz, H., Duval, M.C., Breheret, E., Lindqvist, L., Solvent effects on acetophenone photoreduction studied by laser photolysis, The Journal of Physical Chemistry. (1972) 76 821–822.
  • [3] Scharf, G., Winefordner, J.D., Phosphorescence characteristics of acetophenone, benzophenone, p-aminobenzophenone and michlercs ketone in various environments, Talanta. (1986) 33 17–25.
  • [4] Proksch, P., Rodriguez, E., Chromenes and benzofurans of the asteraceae, their chemistry and biological significance, Phytochemistry. (1983) 22 2335–2348.
  • [5] Tomás-Barberán, F., Iniesta-Sanmartín, E., Tomás-Lorente, F., Rumbero, A., Antimicrobial phenolic compounds from three Spanish Helichrysum species, Phytochemistry. (1990) 29 1093–1095.
  • [6] Buckle, D.R., Smith, H., Cantello, B.C.C., Substituted ω-nitroacetophenones, (1976).
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  • [8] Sivakumar, P.M., Sheshayan, G., Doble, M., Experimental and QSAR of Acetophenones as Antibacterial Agents, Chemical Biology & Drug Design. (2008) 72 303–313.
  • [9] Sittig, M., Pharmaceutical manufacturing encyclopedia, Noyes publ., 1988.
  • [10] Amin, S.I., Walker, J.A., Process for preparing arylalkanoic acid derivatives, 1979.
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  • [13] Cacchi, S., Fabrizi, G., Gavazza, F., Goggiamani, A., Palladium-Catalyzed Reaction of Aryl Iodides with Acetic Anhydride. A Carbon Monoxide-Free Synthesis of Acetophenones, Organic Letters. (2003) 5 289–291.
  • [14] Prasad, Y.R., Rao, a S., Rambabu, R., Synthesis of Some 4 ’-Amino Chalcones and their Antiinflammatory and Antimicrobial Activity, Asian Journal of Chemistry. (2009) 21 907–914.
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  • [18] Piro, O.E., Echeverría, G.A., Lizarraga, E., Romano, E., Catalán, C.A.N., Brandán, S.A., Molecular structure of 4-hidroxy-3-(3-methyl-2-butenyl) acetophenone, a plant antifungal, by X-ray diffraction, DFT calculation, and NMR and FTIR spectroscopy., Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy. (2013) 101 196–203.
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  • [24] Udhayakala, P., Rajendiran, T. V, Seshadri, S., Gunasekaran, S., Quantum chemical vibrational study, molecular property and HOMO-LUMO energies of 3-bromoacetophenone for Pharmaceutical application, Journal of Chemical and Pharmaceutical Research. (2011) 3 610–625.
  • [25] Subramanian, M.K., Anbarasan, P.M., Ilangovan, V., Babu, S.M., FT-IR, NIR-FT-Raman and gas phase infrared spectra of 3-aminoacetophenone by density functional theory and ab initio Hartree-Fock calculations, Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy. (2008) 71 59–67.
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  • [27] Jeyavijayan, S., Molecular structure, spectroscopic (FTIR, FT-Raman, 13C and 1H NMR, UV), polarizability and first-order hyperpolarizability, HOMO-LUMO analysis of 2,4-difluoroacetophenone., Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy. (2015) 136 Pt B 553–66.
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  • [35] Jamróz, M.H., Vibrational energy distribution analysis (VEDA): scopes and limitations., Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. (2013) 114 220–230.
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  • [38] Fabian, J., TDDFT-calculations of Vis/NIR absorbing compounds, Dyes and Pigments. (2010) 84 36–53.
  • [39] Ditchfield, R., Molecular Orbital Theory of Magnetic Shielding and Magnetic Susceptibility, The Journal of Chemical Physics. (1972) 56 5688–5691.
  • [40] Wolinski, K., Hinton, J.F., Pulay, P., Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations, Journal of the American Chemical Society. (1990) 112 8251–8260.
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  • [43] Karabacak, M., Kose, E., Atac, A., Sas, E.B., Asiri, A.M., Kurt, M., Experimental (FT-IR, FT-Raman, UV–Vis, 1H and 13CNMR) and computational (density functional theory) studies on 3-bromophenylboronic acid, Journal of Molecular Structure. (2014) 1076 358–372.
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Toplam 74 adet kaynakça vardır.

Ayrıntılar

Konular Mühendislik
Bölüm Araştırma Makalesi
Yazarlar

Etem Kose

Yayımlanma Tarihi 1 Aralık 2016
Yayımlandığı Sayı Yıl 2016 Cilt: 17 Sayı: 4

Kaynak Göster

APA Kose, E. (2016). THE SPECTROSCOPIC ANALYSIS OF 2,4’-DIBROMOACETOPHENONE MOLECULEBY USING QUANTUM CHEMICAL CALCULATIONS. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering, 17(4), 677-702. https://doi.org/10.18038/aubtda.267115
AMA Kose E. THE SPECTROSCOPIC ANALYSIS OF 2,4’-DIBROMOACETOPHENONE MOLECULEBY USING QUANTUM CHEMICAL CALCULATIONS. AUBTD-A. Aralık 2016;17(4):677-702. doi:10.18038/aubtda.267115
Chicago Kose, Etem. “THE SPECTROSCOPIC ANALYSIS OF 2,4’-DIBROMOACETOPHENONE MOLECULEBY USING QUANTUM CHEMICAL CALCULATIONS”. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering 17, sy. 4 (Aralık 2016): 677-702. https://doi.org/10.18038/aubtda.267115.
EndNote Kose E (01 Aralık 2016) THE SPECTROSCOPIC ANALYSIS OF 2,4’-DIBROMOACETOPHENONE MOLECULEBY USING QUANTUM CHEMICAL CALCULATIONS. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering 17 4 677–702.
IEEE E. Kose, “THE SPECTROSCOPIC ANALYSIS OF 2,4’-DIBROMOACETOPHENONE MOLECULEBY USING QUANTUM CHEMICAL CALCULATIONS”, AUBTD-A, c. 17, sy. 4, ss. 677–702, 2016, doi: 10.18038/aubtda.267115.
ISNAD Kose, Etem. “THE SPECTROSCOPIC ANALYSIS OF 2,4’-DIBROMOACETOPHENONE MOLECULEBY USING QUANTUM CHEMICAL CALCULATIONS”. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering 17/4 (Aralık 2016), 677-702. https://doi.org/10.18038/aubtda.267115.
JAMA Kose E. THE SPECTROSCOPIC ANALYSIS OF 2,4’-DIBROMOACETOPHENONE MOLECULEBY USING QUANTUM CHEMICAL CALCULATIONS. AUBTD-A. 2016;17:677–702.
MLA Kose, Etem. “THE SPECTROSCOPIC ANALYSIS OF 2,4’-DIBROMOACETOPHENONE MOLECULEBY USING QUANTUM CHEMICAL CALCULATIONS”. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering, c. 17, sy. 4, 2016, ss. 677-02, doi:10.18038/aubtda.267115.
Vancouver Kose E. THE SPECTROSCOPIC ANALYSIS OF 2,4’-DIBROMOACETOPHENONE MOLECULEBY USING QUANTUM CHEMICAL CALCULATIONS. AUBTD-A. 2016;17(4):677-702.