Ryu Yamasaki
Misuzu Harada
Rino Nagata
Ai Ito
Kazuo Fukuda
Iwao Okamoto
Acid-induced conformational switching system composed with acetanilide derivatives was first reported in 2003 (Yamasaki, R et al.). However, this system was not operative for benzanilide derivative. To make this switching system work in a benzanilide derivative, we replaced phenyl group with perfluorophenyl group which interact with phenyl group. A replacement of perfluorobenzoyl group found to make N-methylbenzanilide derivatives sensitive to substituents on the anilino group. Finally, N-[p-(dimethylamino)phenyl]-N-phenylbenzanilide changed its stable conformation by adding acid, and the conformational transition was observed by NMR, due to the higher rotational barrier of perfluorobenzoyl substituted benzanilide derivative.
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