Department of Chemistry, Federal University of Lavras , Lavras, MG 37200-000, Brazil.
J Phys Chem A. 2014 Jan 16;118(2):503-7. doi: 10.1021/jp410458w. Epub 2014 Jan 3.
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.
在气相中，3-氟哌啶阳离子和类似物中强烈的 gauche 偏好以及 F-C-C-N(+) 片段是由静电相互作用决定的，这些相互作用既可以是氢键 F···H(N(+))，也可以是 F/N(+) 吸引力。在大多数生化过程发生的水溶液中，静电效应被强烈减弱，超共轭被计算为至少与路易斯型相互作用具有竞争力。
