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Investigation of structure, vibrational and NMR spectra of oxycodone and naltrexone: A combined experimental and theoretical study

Tavakol, H ; Sharif University of Technology

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  1. Type of Document: Article
  2. DOI: 10.1016/j.saa.2011.03.038
  3. Abstract:
  4. In this work, two important opioid antagonists, naltrexone and oxycodone, were prepared from thebaine and were characterized by IR, 1H NMR and 13C NMR spectroscopy. Moreover, computational NMR and IR parameters were obtained using density functional theory (DFT) at B3LYP/6-311++G* * level of theory. Complete NMR and vibrational assignment were carried out using the observed and calculated spectra. The IR frequencies and NMR chemical shifts, determined experimentally, were compared with those obtained theoretically from DFT calculations, showed good agreements. The RMS errors observed between experimental and calculated data for the IR absorptions are 85 and 105 cm-1, for the 1H NMR peaks are 0.87 and 0.17 ppm and for those of 13C NMR are 5.6 and 5.3 ppm, respectively for naltrexone and oxycodone
  5. Keywords:
  6. Density functional ; Naltrexone ; Density functionals ; DFT calculation ; IR absorption ; IR frequencies ; Naltrexone ; NMR chemical shifts ; NMR peaks ; NMR spectroscopy ; NMR spectrum ; RMS errors ; Theoretical study ; Vibration ; Vibrational assignment ; Nuclear magnetic resonance spectroscopy ; Density functional theory ; Narcotic antagonist ; Article ; Chemical structure ; Chemistry ; Infrared spectroscopy ; Raman spectrometry ; X ray crystallography ; Crystallography, X-ray ; Magnetic esonance spectroscopy ; Models, molecular ; Narcotic antagonists ; Oxycodone ; Quantum theory ; Spectroscopy, fourier transform infrared ; Spectrum analysis, Raman
  7. Source: Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy ; Volume 79, Issue 3 , 2011 , Pages 574-582 ; 13861425 (ISSN)
  8. URL: http://www.sciencedirect.com/science/article/pii/S1386142511002010