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

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
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Physical Chemistry/Chemical Physics
Journal title
JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM
ISSN journal
0166-1280 → 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.