ON THE STABILIZATION OF THE SYN-ROTAMER OF AMINO-ACID CARBAMATE DERIVATIVES BY HYDROGEN-BONDING

Authors
MARCOVICIMIZRAHI D GOTTLIEB HE MARKS V NUDELMAN A
Citation
D. Marcovicimizrahi et al., ON THE STABILIZATION OF THE SYN-ROTAMER OF AMINO-ACID CARBAMATE DERIVATIVES BY HYDROGEN-BONDING, Journal of organic chemistry, 61(24), 1996, pp. 8402-8406
Citations number
7
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
61
Issue
24
Year of publication
1996
Pages
8402 - 8406
Database
ISI
SICI code
0022-3263(1996)61:24<8402:OTSOTS>2.0.ZU;2-P
Abstract
The syn-rotamers of carbamate derivatives of alpha-amino acids are sho wn to be stabilized by the formation of H-bond complexes with carboxyl ic acid moieties in solution. This effect is, as expected, concentrati on and temperature dependent. Thermodynamic parameters (both Delta G d egrees and Delta G double dagger) for N-Boc-alanine were determined by NMR in the +/-60 degrees C range.