Geometrical isomerism, tautomerism and conformational charges of 2-propenal-3-amine in its neutral and protonated forms

Authors
Garro, JC Manzanares, GD Zamarbide, GN Ponce, CA Estrada, MR Jauregui, EA
Citation
Jc. Garro et al., Geometrical isomerism, tautomerism and conformational charges of 2-propenal-3-amine in its neutral and protonated forms, J MOL ST-TH, 545, 2001, pp. 17-27
Citations number
10
Categorie Soggetti
Physical Chemistry/Chemical Physics
Journal title
JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM
ISSN journal
01661280 → ACNP
Volume
545
Year of publication
2001
Pages
17 - 27
Database
ISI
SICI code
0166-1280(20010709)545:<17:GITACC>2.0.ZU;2-F
Abstract
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. V. All rights reserved.