Amide conformational switching induced by protonation of aromatic substituent.
作者信息
Yamasaki Ryu, Tanatani Aya, Azumaya Isao, Saito Shoichi, Yamaguchi Kentaro, Kagechika Hiroyuki
机构信息
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
出版信息
Org Lett. 2003 Apr 17;5(8):1265-7. doi: 10.1021/ol034344g.
PMID:12688735
Abstract
[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.
摘要
Zotero 插件