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

Artikel i vetenskaplig tidskrift
Författare Alavi Karim
Nils Schulz
Hanna Andersson
Bijan Nekoueishahraki
Anna-Carin Carlsson
Daniel Sarabi
Arto Valkonen
Kari Rissanen
Jürgen Gräfenstein
Sandro Keller
Mate Erdelyi
Publicerad i Journal of the American Chemical Society
Volym 140
Nummer/häfte 50
Sidor 17571-17579
ISSN 00027863
Publiceringsår 2018
Publicerad vid Svenskt NMR-centrum vid Göteborgs universitet
Institutionen för kemi och molekylärbiologi
Sidor 17571-17579
Språk en
Länkar https://doi.org/10.1021/jacs.8b0936...
Ämneskategorier Organisk kemi, Kvantkemi

Sammanfattning

© 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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