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Issue 20, 2020
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Observations of tetrel bonding between sp3-carbon and THF

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Abstract

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.

Graphical abstract: Observations of tetrel bonding between sp3-carbon and THF

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Article information


Submitted
16 Mar 2020
Accepted
05 May 2020
First published
07 May 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 5289-5293
Article type
Edge Article

Observations of tetrel bonding between sp3-carbon and THF

V. L. Heywood, T. P. J. Alford, J. J. Roeleveld, S. J. Lekanne Deprez, A. Verhoofstad, J. I. van der Vlugt, S. R. Domingos, M. Schnell, A. P. Davis and T. J. Mooibroek, Chem. Sci., 2020, 11, 5289 DOI: 10.1039/D0SC01559H

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