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/
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
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