Cyclophosphamide and isophosphamide - DFT conformational studies in the gas phase and solution
PBN-AR
Instytucja
Wydział Chemii (Uniwersytet Gdański)
Informacje podstawowe
Główny język publikacji
en
Czasopismo
Journal of Molecular Graphics & Modelling
ISSN
1093-3263
EISSN
Wydawca
DOI
URL
Rok publikacji
2019
Numer zeszytu
Strony od-do
243-257
Numer tomu
90
Identyfikator DOI
Liczba arkuszy
0.7
Słowa kluczowe
en
Cyclophosphamide
isophosphamide
DFT conformational studies
NBO analysis
Streszczenia
Język
en
Treść
Cyclophosphamide and isophosphamide have been subjected to comprehensive conformational studies in the vacuum and solution using the SMD solvation model. Vacuum calculations were conducted using the B3LYP, M05-2X, M06-2X and uB97XD functionals. Natural bond orbital (NBO) analysis has been performed for selected geometries. A preference for a chair conformation with the axial P¼O bond is shown (1C4). The 5S0 conformation is 1.25e2.31 kcal/mol and 1.72e2.92 kcal/mol higher in energy than the global minimum conformations of cyclophosphamide and isophosphamide, respectively. In the gas phase, the chair conformation with the equatorial P¼O bond (4C1) is of comparable stability or less stable than the skew form, depending on the method used, while it is slightly more favored than the 5S0 conformation in solution. The stereoelectronic effects do not differentiate the ring conformer stability. The steric strains between N(EtCl)1e2 and the C4 and C6 carbon atoms mainly influence the stability of cyclophosphamide and isophosphamide conformers.
Inne
System-identifier
UOG09e9cb3784674b2b9f5b346ffbdf7dff
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