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5-((4-brom-2-klorfenoksi)metil)oksazolidin-2-on ve 5-((2-brom-4-klorfenoksi)metil)oksazolidin-2-on bileşiklerinin Sentezi ve Teorik Hesaplamaları

Year 2020, , 500 - 511, 15.06.2020
https://doi.org/10.17798/bitlisfen.567909

Abstract

Bu çalışmada 5-((4-brom-2-klorfenoksi)metil)oksazolidin-2-on
ve 5-((2-brom-4-klorfenoksi)metil)oksazolidin-2-on bileşikleri sentezlenip
teorik spektroskopik özellikleri B3LYP/6-31G (d,p) ve HF/6-31G (d) temel
setleri kullanılarak incelenmiştir. Bu amaçla çalışılan bileşiklerin öncelikle
DFT, HF yöntemleri ve 6-31G (d,p)/ 6-31G (d) temel setleri kullanılarak
optimizasyonu yapılmıştır. Gaussian G09W paket programı kullanılarak 1H-NMR,
13C-NMR kimyasal kayma değerleri hesaplanmıştır. Deneysel ve teorik
kimyasal kayma değerleri için regrasyon analizleri yapılmıştır. Ayrıca
moleküllerin bağ uzunluklarıyla mulliken yükleri, en yüksek dolu moleküler
orbital enerjisi (HOMO) ve en düşük boş moleküler orbital enerjisi (LUMO)
değerleri hesaplanmıştır. HOMO ve LUMO enerji değerlerinden yararlanılarak
iyonizasyon potansiyeli elektron ilgisi, elektronegatiflik,  kimyasal sertlik, kimyasal yumuşaklık gibi
parametrelerin hesaplamaları bir tablo halinde sunulmuştur. Hesaplanan teorik
veriler ile deneysel verilerin uyumlu oldukları görülmüştür. 

References

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  • [2] Shang J., Liu S., Lu L., Ma X., He Y., Deng Y. 2012. Pharmacogenetic study of drug-metabolising enzyme polymorphisms on the risk of anti-tuberculosis drug-induced liver injury: a meta-analysis, Catalysis Communications 28:13–17.
  • [3] Collet M., Ge´nisson Y., Baltas M. 2007. New approach to carbamoyl-polyoxamic acid derivatives through an oxazolidinone synthon, Tetrahedron: Asymmetry 18:1320–1329.
  • [4] Berredjem M., Regainia Z., Dewynter G., Montero J. L., Aouf N. 2006. Simple and efficient synthesis of new chiral N,N′-sulfonyl bis-oxazolidin-2-ones, Heteroatom Chemistry Volume 17, pp.61-65.
  • [5] Zurenko G. E., Gibson J. K., Shinabarger D. L., Aristoff P.A., Ford C. W., Tarpley W. G. 2001. Oxazolidinones: a new class of antibacterials, Current Opinion in Pharmacology, 1:470-476.
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  • [12] Becke A. D. 1988. Density-functional exchange-energy approximation with correct asymptotic behavior, Physical Review A, 38, 3098–3100.
  • [13] Lee C., Yang W., and Parr R. 1988. Development of the Colle- Salvetti correlation energy formula into a functional of the electron density, Physical Review B, 37, 785–789.
  • [14] Wolinski K., Hinton J. F., and Pulay P. 1990. Efficient Implementation of the Gauge-Independent Atomic Orbital Method for NMR Chemical Shift Calculations, Journal of the American Chemical Society, 112, 8251.
  • [15] Lang P. F., Smith B. C. 2016. Single Bond Lengths of Organic Molecules in the Solid State, Global Journal of Science Frontier Research Volume XVI Issue II.
  • [16] Yüksek H., Aytemiz F., Medetalibeyoğlu H., Bahçeci Ş. 2016. DFT/B3LYP ve HF Metodları Kullanılarak 4,5-Dihidro-1H-1,2,4-triazol-5-on Türevlerinin Teorik Özelliklerinin İncelenmesi, Nevşehir Bilim ve Teknoloji Dergisi Cilt 5(2) 46-64.
  • [17] Boopathi M., Udhayakala P., Ramkumaar G. R. 2016. Vibrational spectroscopic (FT-IR, FT-Raman), NMR and electronic structure calculations of metaxalone, Der Pharma Chemica, 8(7):161-172
  • [18] Savithiri S., Arockia Doss M., Rajarajan G., Thanikachalam V., Bharanidharan S., Saleem H. 2014. Spectroscopic (FT-IR, FT-Raman) and quantum mechanical studies of 3t-pentyl-2r,6c-diphenylpiperidin-4-one thiosemicarbazone, Spectrochimica Acta Part A, Molecular and Biomolecular Spectroscopy B:782-792.
  • [19] Palafox M. A. 2000. Scaling Factors for the Prediction of Vibrational Spectra I. Benzene Molecule, International Journal of Quantum Chemistry, Vol. 77, 661–684.
  • [20] Hohenberg P. and Kohn W. 1964. The Inhomogeneous Electron Gas, Physical Review B 136, 864-871.
Year 2020, , 500 - 511, 15.06.2020
https://doi.org/10.17798/bitlisfen.567909

Abstract

References

  • [1] Tikdari A. M., Fozooni S., Hamidian H. 2008. Samarium and Ruthenium (ІІІ) Chloride Catalyzed Synthesis of Unsaturated 2-Phenyl-5(4H)-oxazolone Derivatives under Solvent-free Conditions, Dodecatungstophosphoric Acid, Molecules, 13(12):3246-52.
  • [2] Shang J., Liu S., Lu L., Ma X., He Y., Deng Y. 2012. Pharmacogenetic study of drug-metabolising enzyme polymorphisms on the risk of anti-tuberculosis drug-induced liver injury: a meta-analysis, Catalysis Communications 28:13–17.
  • [3] Collet M., Ge´nisson Y., Baltas M. 2007. New approach to carbamoyl-polyoxamic acid derivatives through an oxazolidinone synthon, Tetrahedron: Asymmetry 18:1320–1329.
  • [4] Berredjem M., Regainia Z., Dewynter G., Montero J. L., Aouf N. 2006. Simple and efficient synthesis of new chiral N,N′-sulfonyl bis-oxazolidin-2-ones, Heteroatom Chemistry Volume 17, pp.61-65.
  • [5] Zurenko G. E., Gibson J. K., Shinabarger D. L., Aristoff P.A., Ford C. W., Tarpley W. G. 2001. Oxazolidinones: a new class of antibacterials, Current Opinion in Pharmacology, 1:470-476.
  • [6] Lee F., Huang T., Chung C. 2003. Method For Producing 5-Aryloxymethyl-2-Oxazolidinones, Patent No.: US 6,562,980 B1.
  • [7] Bratulescu G. 2007. An Excellent Procedure for the Synthesis of Oxazolidin-2-ones, Advanced online publication: Synthesis No. 20, pp 3111–3112.
  • [8] Kamal A., Khanna G. B. R., Krishnaji T., Tekumalla V., Ramu R. 2005. New chemoenzymatic pathway for b-adrenergic blocking agents, Tetrahedron: Asymmetry 16:1485–1494.
  • [9] Bredikhin A. A., Bredikhina Z. A., Zakharychev D. V., Pashagin A. V. 2007. Chiral drugs related to guaifenesin: synthesis and phase properties of methocarbamol and mephenoxalone, Tetrahedron: Asymmetry 18:1239–1244.
  • [10] Uang Y., Chen I., Wang L., Hsu K. 2001. Determination of mephenoxalone in human plasma sample by high-performance liquid chromatography–fluorescence detection, Journal of Chromatography B, 759:91–97.
  • [11] Frisch M.J., Trucks H.B., Schlegel G.E., Scuseria M., Robb J.R., Cheeseman G., Scalmani V., Barone B., Mennucci G.A., Petersson H., Nakatsuji M., Caricato X., Li H.P., Hratchian A.F., Izmaylov J., Bloino G., Zheng J.L, Sonnenberg M., Hada M., Ehara K, Toyota R, Fukuda J, Hasegawa M., Ishida T., Nakajima Y., Honda O., Kitao H., Nakai T., Vreven A., Montgomery J., Peralta F., Ogliaro M., Bearpark J.J., Heyd E., Brothers K.N., Kudin V.N., Staroverov R., Kobayashi J., Normand K., Raghavachari A., Rendell J.C., Burant S.S., Iyengar J., Tomasi M., Cossi N., Rega J.M., Millam M. 2009. Gaussian Inc. Wallingford CT.
  • [12] Becke A. D. 1988. Density-functional exchange-energy approximation with correct asymptotic behavior, Physical Review A, 38, 3098–3100.
  • [13] Lee C., Yang W., and Parr R. 1988. Development of the Colle- Salvetti correlation energy formula into a functional of the electron density, Physical Review B, 37, 785–789.
  • [14] Wolinski K., Hinton J. F., and Pulay P. 1990. Efficient Implementation of the Gauge-Independent Atomic Orbital Method for NMR Chemical Shift Calculations, Journal of the American Chemical Society, 112, 8251.
  • [15] Lang P. F., Smith B. C. 2016. Single Bond Lengths of Organic Molecules in the Solid State, Global Journal of Science Frontier Research Volume XVI Issue II.
  • [16] Yüksek H., Aytemiz F., Medetalibeyoğlu H., Bahçeci Ş. 2016. DFT/B3LYP ve HF Metodları Kullanılarak 4,5-Dihidro-1H-1,2,4-triazol-5-on Türevlerinin Teorik Özelliklerinin İncelenmesi, Nevşehir Bilim ve Teknoloji Dergisi Cilt 5(2) 46-64.
  • [17] Boopathi M., Udhayakala P., Ramkumaar G. R. 2016. Vibrational spectroscopic (FT-IR, FT-Raman), NMR and electronic structure calculations of metaxalone, Der Pharma Chemica, 8(7):161-172
  • [18] Savithiri S., Arockia Doss M., Rajarajan G., Thanikachalam V., Bharanidharan S., Saleem H. 2014. Spectroscopic (FT-IR, FT-Raman) and quantum mechanical studies of 3t-pentyl-2r,6c-diphenylpiperidin-4-one thiosemicarbazone, Spectrochimica Acta Part A, Molecular and Biomolecular Spectroscopy B:782-792.
  • [19] Palafox M. A. 2000. Scaling Factors for the Prediction of Vibrational Spectra I. Benzene Molecule, International Journal of Quantum Chemistry, Vol. 77, 661–684.
  • [20] Hohenberg P. and Kohn W. 1964. The Inhomogeneous Electron Gas, Physical Review B 136, 864-871.
There are 20 citations in total.

Details

Primary Language Turkish
Journal Section Araştırma Makalesi
Authors

Bayhan Karabulut 0000-0002-6677-5023

Cumhur Kırılmış 0000-0002-9190-4800

Publication Date June 15, 2020
Submission Date May 20, 2019
Acceptance Date March 18, 2020
Published in Issue Year 2020

Cite

IEEE B. Karabulut and C. Kırılmış, “5-((4-brom-2-klorfenoksi)metil)oksazolidin-2-on ve 5-((2-brom-4-klorfenoksi)metil)oksazolidin-2-on bileşiklerinin Sentezi ve Teorik Hesaplamaları”, Bitlis Eren Üniversitesi Fen Bilimleri Dergisi, vol. 9, no. 2, pp. 500–511, 2020, doi: 10.17798/bitlisfen.567909.



Bitlis Eren Üniversitesi
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