THE FIRST EXPERIMENTAL-EVIDENCE OF DIFFERENTIAL HYDRATION OF E Z ISOMERS OF STERICALLY HINDERED AMIDES - ONE-DIMENSIONAL STEADY-STATE SELECTIVE INTERMOLECULAR C-13, H-1 OVERHAUSER EFFECT STUDY OF TERT-BUTYLFORMAMIDE/

Citation
Ip. Gerothanassis et al., THE FIRST EXPERIMENTAL-EVIDENCE OF DIFFERENTIAL HYDRATION OF E Z ISOMERS OF STERICALLY HINDERED AMIDES - ONE-DIMENSIONAL STEADY-STATE SELECTIVE INTERMOLECULAR C-13, H-1 OVERHAUSER EFFECT STUDY OF TERT-BUTYLFORMAMIDE/, Tetrahedron letters, 37(36), 1996, pp. 6569-6572
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00404039
Volume
37
Issue
36
Year of publication
1996
Pages
6569 - 6572
Database
ISI
SICI code
0040-4039(1996)37:36<6569:TFEODH>2.0.ZU;2-X
Abstract
One dimensional steady-state selective intermolecular C-13, H-1 Overha user effect study of tert-butylformamide provides the first experiment al evidence of differentical hydration of the Z isomer, compared to th e E isomer, due to the presence of the bulky tert-butyl group; the sig nificant decrease in the population of the Z isomer should be attribut ed to steric effects and deformation of the amide bond with hydration differences playing a significant role. Copyright (C) 1996 Elsevier Sc ience Ltd