Conformational Switch of Benzanilide Derivative Induced by Acid; Effect of Pentafluorobenzoyl Group

Amide-based molecular switches had its limitation on structural diversities. In this work, we designed and synthesized a series of pentafluorobenzoyl-based benzanilide compounds. The conformational ratio of these compounds in solution was correlated linearly with Hammett's sigma p value of the substituent on the anilide ring, reflecting the repulsive interaction between the carbonyl group and the electron-rich aryl group. The addition of acid into the solution of 6, bearing pentafluorobenzoyl group, switched the stable amide conformation. In addition, the sizeable rotational barrier of 6 induced by the pentafluorobenzoyl moiety enabled us to monitor the conformational transition by means of 1H NMR spectroscopy.

Automated summary

In this study, a series of pentafluorobenzoyl-based benzanilide compounds were designed and synthesized. It was found that the conformational ratio of these compounds in solution correlated linearly with the substituent on the anilide ring. Acid addition was able to switch one of the conformations.