Tuning of non-covalent interactions in molecular complexes of fluorinated aromatic compounds

Melandri, Sonia

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https://hdl.handle.net/2142/100520 Copy

Description

Title

Tuning of non-covalent interactions in molecular complexes of fluorinated aromatic compounds

Author(s)

Melandri, Sonia

Contributor(s)

• Favero, Laura B.
• Calabrese, Camilla
• Li, Weixing
• Gutierrez, Imanol Usabiaga
• Maris, Assimo
• Evangelisti, Luca

Issue Date

2018-06-20

Keyword(s)

Structure determination

Abstract

The rotational spectra of pentafluoropyridine-watera and hexafluorobenzene-waterb have shown unambiguously that substitution by fluorine atoms on the ring strongly influences the binding abilities of the aromatic ligand. Differently from their non-substituted counterparts, which form hydrogen bonds with water, both molecules interact with water forming a lone-pair-π-hole interaction between the water oxygen and the ring. We report on a series of rotational spectroscopy studies performed with a Molecular Beam Fourier Transform Microwave spectrometer in which we have tested the binding abilities of a series of fluorine substituted pyridines, namely 2,4-fluoropyridine, 3,5-fluoropyridine and 2,4,6-fluoropyridine with water. In the complexes formed by the di-substituted pyridines, the water moiety lies in the aromatic plane and forms a hydrogen bond with the heterocyclic nitrogen atom and this is by far the most stable conformation. In the tri-substituted pyridine-water complexes two isomers are possible, but the lp-π-hole form is the one observed in the rotational spectrum. More studies involving the pentafluoropyridine and hexafluorobenzene molecules and several ligands such as NH3 and CO have also been performed and the interaction with the π-hole has been characterized.

Publisher

International Symposium on Molecular Spectroscopy

Type of Resource

text

Language

eng

Permalink

http://hdl.handle.net/2142/100520

DOI

10.15278/isms.2018.WK08

Copyright and License Information

Copyright 2018 Sonia Melandri

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