A REVISION OF THE GUTMANN DONOR NUMBERS OF A SERIES OF PHOSPHORAMIDES INCLUDING TEPA

Franco Cataldo

Abstract


The donor numbers (DN) of a series of 20 phosphoramides with general structure (R2N)(X2N)(Y2N)P=O (with R,X and Y alkyl radicals, nitrogen-heterocycles or hydrogen atoms)  were revised on the basis of a series of rather simple considerations. It is shown that all the phosphoramides considered even after the revision are characterized by high DN. In a scale of 163 different type of solvent molecules, the phosphoramides are all collocated with their DN above 35 Kcal/mol till 50 Kcal/mol. The extremely high DN value reported previously for TEPA, is now revised to 50 Kcal/mol. The highest DN values in the phosphoramides considered were found in (aziridino)3P=O (TEPA), (NHEt)3P=O and in (Pyrrolidino)3P=O.

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DOI: http://dx.doi.org/10.17628/ecb.2015.4.92-97

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