Unraveling the Role of Alkyl F on CH-pi Interactions and Uncovering the Tipping Point for Fluorophobicity
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Ams 105 J Organic IP.pdf
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Ams 2014 J of Organic.pdf
Ams, Mark R.
Janesko, Benjamin G.
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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.