Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Electronic Substituent Effects of Guests on the Conformational Network and Binding Behavior of Oxatub[4]arene

Electronic Substituent Effects of Guests on the Conformational Network and Binding Behavior of Oxatub[4]arene
Liu-Pan Yang, Dong-Hao Li, Wei Jiang, Fei Jia
A series of quaternary ammonium guests have been synthesized, and their binding behavior with oxatub[4]arene have been studied. In particular, remote electronic substituents of the guests can significantly affect the binding affinities mainly through a field/inductive effect by following a linear free energy relationship. More surprisingly, oxatub[4]arene, with a complex conformational network, shows a large amplitude of conformational change in response to the remote electronic substituents on the guests. This novel mode of synthetic molecular recognition may also have biological relevance.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01914

DOI: 10.1021/acs.joc.7b01914

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