title: CF3 : An Electron-Withdrawing Substituent for Aromatic Anion Acceptors? "Side-On" versus "On-Top" Binding of Halides.
abstract: 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.
authors.affiliation: Institut für Organische Chemie, RWTH Aachen, Landoltweg 1, 52074, Aachen, Germany. markus.albrecht@oc.rwth-aachen.de.
authors.forename: Markus
authors.identifier: 0000-0002-3501-1477
authors.initials: M
authors.lastname: Albrecht
authors.affiliation: Institut für Organische Chemie, RWTH Aachen, Landoltweg 1, 52074, Aachen, Germany.
authors.forename: Hai
authors.initials: H
authors.lastname: Yi
authors.affiliation: Institut für Organische Chemie, RWTH Aachen, Landoltweg 1, 52074, Aachen, Germany.
authors.forename: Okan
authors.initials: O
authors.lastname: Köksal
authors.affiliation: Institut für Organische Chemie, RWTH Aachen, Landoltweg 1, 52074, Aachen, Germany.
authors.forename: Gerhard
authors.initials: G
authors.lastname: Raabe
authors.affiliation: Department of Chemistry, Nanoscience Center, University of Jyväskylä, Survontie 9 B, 40014, Jyväskylä, Finland.
authors.forename: Fangfang
authors.initials: F
authors.lastname: Pan
authors.affiliation: Department of Chemistry, Nanoscience Center, University of Jyväskylä, Survontie 9 B, 40014, Jyväskylä, Finland.
authors.forename: Arto
authors.initials: A
authors.lastname: Valkonen
authors.affiliation: Department of Chemistry, Nanoscience Center, University of Jyväskylä, Survontie 9 B, 40014, Jyväskylä, Finland.
authors.forename: Kari
authors.initials: K
authors.lastname: Rissanen
keywords: anion recognition; anion-π interactions; computational chemistry; crystal structure; hydrogen bonding