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

Autor:	Ams MR; †Department of Chemistry, Allegheny College, 520 North Main Street, Meadville, Pennsylvania 16335-3902, United States., Fields M; †Department of Chemistry, Allegheny College, 520 North Main Street, Meadville, Pennsylvania 16335-3902, United States., Grabnic T; †Department of Chemistry, Allegheny College, 520 North Main Street, Meadville, Pennsylvania 16335-3902, United States., Janesko BG; ‡Department of Chemistry, Texas Christian University, 2800 Souh University Drive, Fort Worth, Texas 76109, United States., Zeller M; §Department of Chemistry, Youngstown State University, One University Plaza, Youngstown, Ohio 44555, United States., Sheridan R; †Department of Chemistry, Allegheny College, 520 North Main Street, Meadville, Pennsylvania 16335-3902, United States., Shay A; †Department of Chemistry, Allegheny College, 520 North Main Street, Meadville, Pennsylvania 16335-3902, United States.
Jazyk:	angličtina
Zdroj:	The Journal of organic chemistry [J Org Chem] 2015 Aug 07; Vol. 80 (15), pp. 7764-9. Date of Electronic Publication: 2015 Jul 28.
DOI:	10.1021/acs.joc.5b01072
Abstrakt:	Although fluorine often plays an influential role in molecular recognition, little is known about the effect of aliphatic fluorine on the CH-π 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-π 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.
Databáze:	MEDLINE
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