title: Gauche preference of β-fluoroalkyl ammonium salts.
abstract: The strong gauche preference along with the F-C-C-N(+) fragment in 3-fluoropiperidinium cation and analogues, in the gas phase, is dictated by electrostatic interactions, which can be both hydrogen bond F···H(N(+)) and F/N(+) attraction. In aqueous solution, where most biochemical processes take place, electrostatic effects are strongly attenuated and hyperconjugation is calculated to be at least competitive with Lewis-type interactions.
authors.affiliation: Department of Chemistry, Federal University of Lavras , Lavras, MG 37200-000, Brazil.
authors.forename: Josué M
authors.initials: JM
authors.lastname: Silla
authors.forename: Weslley G D P
authors.initials: WG
authors.lastname: Silva
authors.forename: Rodrigo A
authors.initials: RA
authors.lastname: Cormanich
authors.forename: Roberto
authors.initials: R
authors.lastname: Rittner
authors.forename: Cláudio F
authors.initials: CF
authors.lastname: Tormena
authors.forename: Matheus P
authors.initials: MP
authors.lastname: Freitas