CF3 : An Electron-Withdrawing Substituent for Aromatic Anion Acceptors? "Side-On" versus "On-Top" Binding of Halides.
Markus AlbrechtHai YiOkan KöksalGerhard RaabeFangfang PanArto ValkonenKari RissanenPublished in: Chemistry (Weinheim an der Bergstrasse, Germany) (2016)
The ability of multiple CF3 -substituted arenes to act as acceptors for anions is investigated. The results of quantum-chemical calculations show that a high degree of trifluoromethyl substitution at the aromatic ring results in a positive quadrupole moment. However, depending on the polarizability of the anion and on the substitution at the arene, three different modes of interaction, namely Meisenheimer complex, side-on hydrogen bonding, or anion-π interaction, can occur. Experimentally, the side-on as well as a η(2) -type π-complex are observed in the crystal, whereas in solution only side-on binding is found.
Keyphrases
- ionic liquid
- solar cells
- cystic fibrosis
- molecular dynamics
- mass spectrometry
- amino acid
- dna binding
- liquid chromatography
- binding protein
- molecular dynamics simulations
- density functional theory
- tandem mass spectrometry
- molecular docking
- high performance liquid chromatography
- atomic force microscopy
- simultaneous determination
- monte carlo
- gas chromatography
- high resolution
- electron microscopy