title: Unraveling the Role of Alkyl F on CH-π Interactions and Uncovering the Tipping Point for Fluorophobicity.
abstract: 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.
authors.affiliation: †Department of Chemistry, Allegheny College, 520 North Main Street, Meadville, Pennsylvania 16335-3902, United States.
authors.forename: Mark R
authors.initials: MR
authors.lastname: Ams
authors.affiliation: †Department of Chemistry, Allegheny College, 520 North Main Street, Meadville, Pennsylvania 16335-3902, United States.
authors.forename: Michael
authors.initials: M
authors.lastname: Fields
authors.affiliation: †Department of Chemistry, Allegheny College, 520 North Main Street, Meadville, Pennsylvania 16335-3902, United States.
authors.forename: Timothy
authors.initials: T
authors.lastname: Grabnic
authors.affiliation: ‡Department of Chemistry, Texas Christian University, 2800 Souh University Drive, Fort Worth, Texas 76109, United States.
authors.forename: Benjamin G
authors.initials: BG
authors.lastname: Janesko
authors.affiliation: §Department of Chemistry, Youngstown State University, One University Plaza, Youngstown, Ohio 44555, United States.
authors.forename: Matthias
authors.initials: M
authors.lastname: Zeller
authors.affiliation: †Department of Chemistry, Allegheny College, 520 North Main Street, Meadville, Pennsylvania 16335-3902, United States.
authors.forename: Rose
authors.initials: R
authors.lastname: Sheridan
authors.affiliation: †Department of Chemistry, Allegheny College, 520 North Main Street, Meadville, Pennsylvania 16335-3902, United States.
authors.forename: Amanda
authors.initials: A
authors.lastname: Shay