Premium
Electronic structure of the metabolites of cyclophosphamide
Author(s) -
Ulmer W.
Publication year - 1981
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.560190213
Subject(s) - cndo/2 , chemistry , metabolite , singlet state , excited state , dipole , computational chemistry , ground state , ion , photochemistry , molecule , atomic physics , organic chemistry , physics , biochemistry
Some physical and chemical properties of the metabolites of the cancerostat cyclophosphamide (trade name: ENDOXAN) have been calculated with an appropriately prepared CNDO/S‐CI method. The ground state properties (e.g., charge densities and free valences) do not indicate a significant change, compared with the results of cyclophosphamide, and the same fact is also true for the energy levels of the two lowest excited singlet and triplet states. With respect to the dipole transition moments only the metabolite N ‐mustard‐diamido‐phosphoric acid (Friedman acid) differs drastically from cyclophosphamide and the other metabolites. The chemical reactivity has been considered under the aspect of singlet–triplet transitions between quasidegenerate singlet and triplet states. Again Friedman acid behaves quite differently from the other compounds, and only this metabolite exhibits the remarkable ability to act as an alkylating agent via splitting off chloride ions.