Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
4 years ago

Rotational Spectroscopy Probes Water Flipping by Full Fluorination of Benzene

Rotational Spectroscopy Probes Water Flipping by Full Fluorination of Benzene
Luca Evangelisti, Heinrich Mäder, Kai Brendel, Sonia Melandri, Walther Caminati
The topology of the interaction of water with benzene changes drastically upon full HF substitution on the aromatic ring: the weak O−H⋅⋅⋅π hydrogen bond is replaced by a O⋅⋅⋅π linkage, of about the same strength. Hexafluorobenzene–water appears to be the prototype system to investigate this kind of weak bond. The pulsed Fourier transform microwave technique has been used for the detection of the rotational spectra of the normal species and five isotopologues which unambiguously led to the identification of the geometry. Quantum mechanical calculations have been performed to interpret the experimental evidence. Flipping water: The prototype system for the lone-pair⋅⋅⋅π-hole interaction, hexafluorobenzene–water, has been investigated by rotational spectroscopy. Interesting chemical and dynamic features have been found: a) fluorine substitution flips the water bond with benzene, from O−H⋅⋅⋅π to O⋅⋅⋅π hole; b) water is almost freely rotating above the ring and the spectrum of the complex appears to be that of a symmetric top.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201707155

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