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Do docking sites persist upon fluorination? The diadamantylether-aromatics challenge for rotational spectroscopy and theory

Moreno, María Mar Quesada; Pinacho, Pablo; Perez, Cristobal; Šekutor, Marina; Schreiner, R. Peter; Schnell, Melanie (2021) Do docking sites persist upon fluorination? The diadamantylether-aromatics challenge for rotational spectroscopy and theory. Chemistry : a European journal, 27 . pp. 6198-6203. ISSN 0947-6539

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Fluorinated derivatives of biological molecules have proved to be highly efficient atmodifying the biological activity of a given protein through changes in the stability and the kind of docking interactions. These interactions can behindered or facilitated based on the hydrophilic/hydrophobic character of a particular protein region.Diadamantyl ether (C20H30O) possessesbothkinds of docking sites, servingas a good template to model these important contactswith aromatic fluorinated counterparts.We reportherean experimental study on the structures of several complexes between diadamantyl ether andbenzene as well asa series of fluorinated benzenesto analyze the effect of H → F substitution on the interaction and structureof the resulting molecular clustersusing rotational spectroscopy. Allexperimentally observedcomplexes are largely dominated by London dispersioninteractionswith the hydrogen-terminated surface areas of diadamantyl ether. Already singlesubstitution of one hydrogen atom with fluorine changes the preferred docking site of the complexes. However, the overall contributions of the different intermolecular interactions aresimilar for the different complexes, contrary to previous studies focusing on the difference in interactions using fluorinated and non-fluorinated molecules.

Item Type: Article
Uncontrolled Keywords: diadamantyl ether ; dispersion interactions ; fluorination ; high-resolution rotational spectroscopy ; weakly-bound complexes
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Depositing User: Marina Šekutor
Date Deposited: 13 Apr 2021 07:57
DOI: 10.1002/chem.202100078

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