Conformational, IR, NMR, and EPR analysis of ifosfamide by density functional theory calculation

Osmanoglu Y. E. , TOKATLI A., Sutcu K., Osmanoglu S., UCUN F.

MONATSHEFTE FUR CHEMIE, vol.148, no.2, pp.227-236, 2017 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 148 Issue: 2
  • Publication Date: 2017
  • Doi Number: 10.1007/s00706-016-1824-5
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.227-236


The optimized molecular structure, vibrational frequencies, H-1 and C-13 NMR chemical shifts, and EPR hyperfine splittings of 3-(2-chloroethyl)-2-[(2-chloroethyl) amino] tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide (ifosfamide) have been investigated using density functional theory (B3LYP) method with 6-31+G(d, p) basis set for the first time. The calculated optimized geometric parameters (bond lengths and bond angles), vibrational frequencies, NMR chemical shifts, and EPR hyperfine splittings were seen to be in a well agreement with the corresponding experimental data. The experimentalEPRspectrumof themoleculewas recorded after c-irradiation. From the comparison of the calculated and experimental results the formed radical was attributed to a carbon atom-centered radical occurred upon the loss of a chlorine atom due to breakage of the weak C-Cl bonds. So we mentioned that the free electron is transferred to a carbon atom through intramolecular rearrangement while the molecular charge changes to neutral situation, giving NHC alpha H2C beta H2 radical.