Unraveling the Role of Alkyl F on CH-pi Interactions and Uncovering the Tipping Point for Fluorophobicity

作者:Ams Mark R*; Fields Michael; Grabnic Timothy; Janesko Benjamin G; Zeller Matthias; Sheridan Rose; Shay Amanda
来源:Journal of Organic Chemistry, 2015, 80(15): 7764-7769.
DOI:10.1021/acs.joc.5b01072

摘要

Although fluorine often plays an influential role in molecular recognition, little is known about the effect of aliphatic fluorine on the CH-pi interaction in solution. A series of molecular balances were synthesized that contain fluorinated and nonfluorinated alkyl groups. Our findings indicate that fluorine's polarizing ability does enhance CH-7r binding and depends on molecular orientation. Surprisingly, when the terminal end of the alkyl group is completely fluorinated, the balance tips toward fluorophobicity and assumes an unusual constrained conformation.

  • 出版日期2015-8-7