Amide conformational switching induced by protonation of aromatic substituent.
Amide conformational switching induced by protonation of aromatic substituent.
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DOI：
10.1021/ol034344g
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发表时间：
2003-03
期刊：
影响因子：
5.2
通讯作者：
R. Yamasaki;Aya Tanatani;I. Azumaya;Shoichi Saito;K. Yamaguchi;H. Kagechika
中科院分区：
文献类型：
--
作者：
R. Yamasaki;Aya Tanatani;I. Azumaya;Shoichi Saito;K. Yamaguchi;H. Kagechika
[反应：见正文] N-甲基乙酰苯胺芳环上引入吸电子基团降低了顺式构象异构体的比例，该比例与取代基的哈米特西格玛值有很好的相关性。这些空间特性可用于通过 4-[双(二甲基氨基)]-N-甲基乙酰苯胺或 N-[对-(二甲基氨基)苯基]-N-苯基乙酰胺的芳族取代基处的质子化来实现酰胺构象转换。
[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.