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

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2015-07-08
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Ams, Mark R.
Fields, Michael
Grabnic, Timothy
Janesko, Benjamin G.
Zeller, Matthias
Sheridan, Rose
Shay, Amanda
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Abstract
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.
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Chemistry
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This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/acs.joc.5b01072.
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Ams, Mark R., et al. 2015. "Unraveling the Role of Alkyl F on CH−π Interactions and Uncovering the Tipping Point for Fluorophobicity." The Journal of Organic Chemistry 80, no. 15: 7764-7769.
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American Chemical Society
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