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

Persistent URL
Author(s)
Ams, Mark R.
Fields, Michael
Grabnic, Timothy
Janesko, Benjamin G.
Zeller, Matthias
Sheridan, Rose
Shay, Amanda
Date Issued
July 8, 2015
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.
Journal
The Journal of Organic Chemistry
Department
Chemistry
Citation
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.
Publisher
American Chemical Society
Version of Article
Postprint
Embargo
This version of the article is available for viewing to the public after July 8, 2016
DOI
10.1021/acs.joc.5b01072
ISSN
0022-3263
1520-6904
Rights
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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