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.

Observation of conformational transition of perfluorophenyl substituted benzanilide derivative

2019 Fall National Meeting

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