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Synthesis of N-Urethane-protected gamma-amino-functionalized butenoates and tautomeric studies by means of NMR, X-ray crystallography and ab initio calculations

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Synthesis of N-Urethane-protected gamma-amino-functionalized butenoates and tautomeric studies by means of NMR, X-ray crystallography and ab initio calculations (EN)
Gavrielatos, E (EN)
Theologitis, M (EN)
Adam, MA (EN)
Papadopoulos, M (EN)
Reis, H (EN)
Markopoulos, J (EN)
Detsi, A (EN)
Igglessi-Markopoulou, O (EN)
journalArticle (EN)
2014-03-01T01:51:21Z
2001 (EN)
N-Urethane-protected gamma -amino-alpha -cyano-beta -hydroxybutenoates were synthesized as potential statine analogues and the stability of their possible tautomers was assessed using NMR, X-ray crystallography and ab initio calculations. The results establish that the cis-enol tautomeric form is the most stable one both in solution (CDCl3) and in the solid phase. In full agreement with the experimental data, the theoretical calculations predicted that the cis-enol tautomer would be the minimum energy tautomer. (EN)
Chemistry, Organic (EN)
C-acylation reactions (EN)
PEPTIDES (EN)
SPECTROSCOPY (EN)
AM1 (EN)
ACTIVE METHYLENE-COMPOUNDS (EN)
TETRAMIC ACIDS (EN)
gamma-amino-alpha-cyano-beta-hydroxybutenoates tautomeric studies (EN)
ENOL-TAUTOMERISM (EN)
INHIBITORS (EN)
HYDROXYSUCCINIMIDE ESTERS (EN)
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (EN)
English
WILEY-V C H VERLAG GMBH (EN)
National Technical University of Athens
Digital Library of National Technical University of Athens | Dspace@NTUA
Κεντρική Βιβλιοθήκη Ε.Μ.Π.
Ιδρυματικό Αποθετήριο
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