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

Spectrochimica Acta Part A 79 (2011) 574–582

Hossein Tavakol,∗, Maryam Esfandyari, Salman Taheri, Akbar Heydari

Abstract

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 105cm−1, for the 1H NMR peaks are 0.87 and 0.17ppm and for those of 13C NMR are 5.6 and 5.3 ppm, respectively for naltrexone and oxycodone.