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Updated: May 7, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Effect of aromatic ring fluorination on CH···π interactions: rotational spectrum and structure of the
Nathan W Ulrich1, Tabitha S Songer, Rebecca A Peebles
1Department of Chemistry, Eastern Illinois University, 600 Lincoln Avenue, Charleston, IL 61920, USA. sapeebles@eiu.edu.
Abstract:
The rotational spectra for the normal isotopic species and for six (13)C singly substituted isotopologues (in natural abundance) of the fluorobenzene···acetylene (C6H5F···HCCH) weakly bound dimer have been measured in the 6.5-18.5 GHz region using chirped-pulse Fourier-transform microwave spectroscopy. The HCCH molecule interacts with the fluorobenzene via a CH···π contact and is determined to lie almost over the center of, and approximately perpendicular to, the aromatic ring, with an H···π distance (perpendicular distance from the H atom to the ring plane) of around 2.492(47) Å; a slight tilt of HCCH towards the para carbon atom of the fluorobenzene is evident. Binding energies of this complex and related benzene and fluorobenzene dimers obtained from the pseudodiatomic approximation are compared and indicate that fluorobenzene···acetylene lies among the more weakly bound of the complexes exhibiting some type of CH···π interaction.
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