Further evidence on the importance of fluorous-fluorous interactions in supramolecular chemistry: a combined structural and computational study

Omorodion, Harrison, Twamley, Brendan, Platts, James Alexis ORCID: https://orcid.org/0000-0002-1008-6595 and Baker, Robert James 2015. Further evidence on the importance of fluorous-fluorous interactions in supramolecular chemistry: a combined structural and computational study. Crystal Growth and Design 15 (6) , pp. 2835-2841. 10.1021/acs.cgd.5b00254

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Abstract

The solid-state structures of CF3(CF2)5CH2CO2H and a fluorous triazole are reported, both of which display a wide variety and large number of noncovalent interactions in their packing. The solid-state structure of CF3(CF2)5CH2CO2H is stabilized by multiple F···F contacts but only one C–H···F–C interaction, as well as O–H···O and C–H···O hydrogen bonds. In contrast to other reported structures, the torsion angles in the fluorous chain are close to 180°, which means that the fluorine atoms are eclipsed. A DFT study of the interactions in both compounds show that F···F interactions, along with stacking and C–H···F and C–H···O contacts, are individually weakly energetically stabilizing, but collectively, they can give rise to interaction energies of up to 13 kcal mol–1. A topological approach to the interactions using atoms-in-molecules (AIM) theory reveals that there are bond critical points between the C–F···F–C interactions as well as C–F···H–C interactions that are not recognized when using only the van der Waals distances.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Advanced Research Computing @ Cardiff (ARCCA) Chemistry
Subjects:	Q Science > QD Chemistry
Publisher:	American Chemical Society
ISSN:	1528-7483
Last Modified:	28 Oct 2022 09:03
URI:	https://orca.cardiff.ac.uk/id/eprint/73097

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