Enaminones may be pro-drugs releasing via proton catalyzed hydrolysis a pri
mary amine, which may be an actual drug. The prototype enaminone: 2-propena
l-3-amine has been subjected to quantum chemical studies. Its various tauto
mers and their conformers were investigated in a search for the most likely
reactive form. Protonation study revealed the following order of basicity:
O > C > N for favorable sites of protonation. (C) 2001 Elsevier Science B.
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