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dc.contributor.authorAms, Mark R.
dc.contributor.authorFields, Michael
dc.contributor.authorGrabnic, Timothy
dc.contributor.authorJanesko, Benjamin G.
dc.contributor.authorZeller, Matthias
dc.contributor.authorSheridan, Rose
dc.contributor.authorShay, Amanda
dc.date.accessioned2015-10-15T15:57:45Z
dc.date.available2015-10-15T15:57:45Z
dc.date.issued2015-07-08
dc.identifier.citationAms, 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.en_US
dc.identifier.issn0022-3263
dc.identifier.issn1520-6904
dc.identifier.urihttp://hdl.handle.net/10456/40013
dc.description.abstractAlthough 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.en_US
dc.language.isoen_USen_US
dc.publisherAmerican Chemical Societyen_US
dc.relation.ispartofThe Journal of Organic Chemistryen_US
dc.relation.isversionofhttp://dx.doi.org/10.1021/acs.joc.5b01072en_US
dc.rightsThis 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.en_US
dc.titleUnraveling the Role of Alkyl F on CH-pi Interactions and Uncovering the Tipping Point for Fluorophobicityen_US
dc.description.versionPostprinten_US
dc.contributor.departmentChemistryen_US
dc.description.embargoThis version of the article is available for viewing to the public after July 8, 2016en_US
dc.citation.volume80en_US
dc.citation.issue15en_US
dc.citation.spage7764en_US
dc.citation.epage7769en_US
dc.identifier.doi10.1021/acs.joc.5b01072
dc.contributor.avlauthorAms, Mark R.


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