Theoretical study of hydroxylation reaction mechanism and subsequent carcinogenic metabolites for nitrosopyrrolidine

The hydroxylation reaction mechanism and the formation of the ultimate carcinogens of nitrosopyrrolidine (NPYR) has been theoretically investigated at the B3LYP/6-31G∗∗ level. For the hydroxylation reaction of NPYR, there are both anti-way and syn-way by atomic oxygen. And it is found that the path of the oxydation of the CH bond is easier than the path involving Singlet/Triplet crossing. The subsequent carcinogenic metabolites of α-hydroxy-NPYR involve isomerization and protonation.