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Carbon's Three-Center, Four-Electron Tetrel Bond, Treated Experimentally

Journal article
Authors Alavi Karim
Nils Schulz
Hanna Andersson
Bijan Nekoueishahraki
Anna-Carin Carlsson
Daniel Sarabi
Arto Valkonen
Kari Rissanen
Jürgen Gräfenstein
Sandro Keller
Mate Erdelyi
Published in Journal of the American Chemical Society
Volume 140
Issue 50
Pages 17571-17579
ISSN 00027863
Publication year 2018
Published at Swedish NMR Centre at Göteborg University
Department of Chemistry and Molecular Biology
Pages 17571-17579
Language en
Links https://doi.org/10.1021/jacs.8b0936...
Subject categories Organic Chemistry, Quantum chemistry

Abstract

© 2018 American Chemical Society. Tetrel bonding is the noncovalent interaction of group IV elements with electron donors. It is a weak, directional interaction that resembles hydrogen and halogen bonding yet remains barely explored. Herein, we present an experimental investigation of the carbon-centered, three-center, four-electron tetrel bond, [N-C-N]+, formed by capturing a carbenium ion with a bidentate Lewis base. NMR-spectroscopic, titration-calorimetric, and reaction-kinetic evidence for the existence and structure of this species is reported. The studied interaction is by far the strongest tetrel bond reported so far and is discussed in comparison with the analogous halogen bond. The necessity of the involvement of a bidentate Lewis base in its formation is demonstrated by providing spectroscopic and crystallographic evidence that a monodentate Lewis base induces a reaction rather than stabilizing the tetrel bond complex. A vastly decreased Lewis basicity of the bidentate ligand or reduced Lewis acidity of the carbenium ion weakens - or even prohibits - the formation of the tetrel bond complex, whereas synthetic modifications facilitating attractive orbital overlaps promote it. As the geometry of the complex resembles the SN2 transition state, it provides a model system for the investigation of fundamental reaction mechanisms and chemical bonding theories.

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