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RESEARCH PRODUCT
CF3: An Electron-Withdrawing Substituent for Aromatic Anion Acceptors? “Side-On” versus “On-Top” Binding of Halides
Markus AlbrechtFangfang PanGerhard RaabeArto ValkonenOkan KöksalKari RissanenHai Yisubject
Trifluoromethyl010405 organic chemistryHydrogen bondChemistryStereochemistryOrganic Chemistryanion acceptorsSubstituentGeneral ChemistryCrystal structureCF3-substituted arenes010402 general chemistryRing (chemistry)01 natural sciencesCatalysisMeisenheimer complex3. Good health0104 chemical sciencesCrystallographychemistry.chemical_compoundPolarizabilityPolar effectta116description
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2016-01-19 | Chemistry: A European Journal |