Issue 20, 2020

Observations of tetrel bonding between sp3-carbon and THF

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

Supplementary files

Article information

Article type
Edge Article
Submitted
16 mar. 2020
Accepted
05 maí 2020
First published
07 maí 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2020,11, 5289-5293

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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