Victoria L. Heywood, Thomas P. J. Alford, Julius J. Roeleveld, Siebe J. Lekanne Deprez, Abraham Verhoofstad, Jarl Ivar van der Vlugt, Sergio R. Domingos, Melanie Schnell, Anthony P. Davis and Tiddo J. Mooibroek
Chem. Sci. 2020, 11, 5289-5293
We report the direct observation of tetrel bonding interactions between sp3-carbons of the supramolecular synthon 3,3-dimethyl-tetracyanocyclopropane (1) and tetrahydrofuran in the gas and crystalline phase. The intermolecular contact is established via σ-holes and is driven mainly by electrostatic forces. The complex manifests distinct binding geometries when captured in the crystalline phase and in the gas phase. We elucidate these binding trends using complementary gas phase quantum chemical calculations and find a total binding energy of −11.2 kcal mol−1 for the adduct. Our observations pave the way for novel strategies to engineer sp3-C centred non-covalent bonding schemes for supramolecular chemistry.