Amide conformational switching induced by protonation of aromatic substituent.
[reaction: see text] Introduction of an electron-withdrawing group on the aromatic ring of N-methylacetanilide decreased the ratio of the cis conformer, and the ratio correlates well with the Hammett sigma values of the substituents. These steric properties can be applied to achieve amide conformational switching by protonation at the aromatic substituent of 4-[bis(dimethylamino)]-N-methylacetanilide or N-[p-(dimethylamino)phenyl]-N-phenylacetamide.
Yamasaki
Ryu
R
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Tanatani
Aya
A
Azumaya
Isao
I
Saito
Shoichi
S
Yamaguchi
Kentaro
K
Kagechika
Hiroyuki
H