A1 Journal article (refereed)
CF3: An Electron-Withdrawing Substituent for Aromatic Anion Acceptors? “Side-On” versus “On-Top” Binding of Halides (2016)

Albrecht, M., Yi, H., Köksal, O., Raabe, G., Pan, F., Valkonen, A., & Rissanen, K. (2016). CF3: An Electron-Withdrawing Substituent for Aromatic Anion Acceptors? “Side-On” versus “On-Top” Binding of Halides. Chemistry: A European Journal, 22(20), 6956–6963. https://doi.org/10.1002/chem.201600249

JYU authors or editors

Publication details

All authors or editors: Albrecht, Markus; Yi, Hai; Köksal, Okan; Raabe, Gerhard; Pan, Fangfang; Valkonen, Arto; Rissanen, Kari

Journal or series: Chemistry: A European Journal

ISSN: 0947-6539

eISSN: 1521-3765

Publication year: 2016

Volume: 22

Issue number: 20

Pages range: 6956–6963

Publisher: Wiley - V C H Verlag GmbH & Co. KGaA

Publication country: Germany

Publication language: English

DOI: https://doi.org/10.1002/chem.201600249

Publication open access: Not open

Publication channel open access:


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 η2‐type π‐complex are observed in the crystal, whereas in solution only side‐on binding is found.

Keywords: chemical bonds; hydrogen bonds

Free keywords: CF3-substituted arenes; anion acceptors

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Ministry reporting: Yes

Reporting Year: 2016

JUFO rating: 2

Last updated on 2021-18-06 at 18:50