dc.contributor.author | Karim, Alavi | |
dc.contributor.author | Schulz, Nils | |
dc.contributor.author | Andersson, Hanna | |
dc.contributor.author | Nekoueishahraki, Bijan | |
dc.contributor.author | Carlsson, Anna-Carin C. | |
dc.contributor.author | Sarabi, Daniel | |
dc.contributor.author | Valkonen, Arto | |
dc.contributor.author | Rissanen, Kari | |
dc.contributor.author | Gräfenstein, Jürgen | |
dc.contributor.author | Keller, Sandro | |
dc.contributor.author | Erdélyi, Máté | |
dc.date.accessioned | 2019-01-07T09:51:48Z | |
dc.date.available | 2019-01-07T09:51:48Z | |
dc.date.issued | 2018 | |
dc.identifier.citation | Karim, A., Schulz, N., Andersson, H., Nekoueishahraki, B., Carlsson, A.-C. C., Sarabi, D., Valkonen, A., Rissanen, K., Gräfenstein, J., Keller, S., & Erdélyi, M. (2018). Carbon’s Three-Center-Four-Electron Tetrel Bond, Treated Experimentally. <i>Journal of the American Chemical Society</i>, <i>140</i>(50), 17571-17579. <a href="https://doi.org/10.1021/jacs.8b09367" target="_blank">https://doi.org/10.1021/jacs.8b09367</a> | |
dc.identifier.other | CONVID_28755391 | |
dc.identifier.other | TUTKAID_79712 | |
dc.identifier.uri | https://jyx.jyu.fi/handle/123456789/60934 | |
dc.description.abstract | 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. NMRspectroscopic, 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 weakensor even prohibitsthe 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. | fi |
dc.format.mimetype | application/pdf | |
dc.language.iso | eng | |
dc.publisher | American Chemical Society | |
dc.relation.ispartofseries | Journal of the American Chemical Society | |
dc.rights | CC BY 4.0 | |
dc.subject.other | tetrel bonding | |
dc.subject.other | Lewis base | |
dc.title | Carbon’s Three-Center-Four-Electron Tetrel Bond, Treated Experimentally | |
dc.type | article | |
dc.identifier.urn | URN:NBN:fi:jyu-201812315340 | |
dc.contributor.laitos | Kemian laitos | fi |
dc.contributor.laitos | Department of Chemistry | en |
dc.contributor.oppiaine | Orgaaninen kemia | fi |
dc.contributor.oppiaine | Organic Chemistry | en |
dc.type.uri | http://purl.org/eprint/type/JournalArticle | |
dc.date.updated | 2018-12-31T10:15:19Z | |
dc.type.coar | http://purl.org/coar/resource_type/c_2df8fbb1 | |
dc.description.reviewstatus | peerReviewed | |
dc.format.pagerange | 17571-17579 | |
dc.relation.issn | 0002-7863 | |
dc.relation.numberinseries | 50 | |
dc.relation.volume | 140 | |
dc.type.version | acceptedVersion | |
dc.rights.copyright | © 2018 American Chemical Society | |
dc.rights.accesslevel | openAccess | fi |
dc.subject.yso | hiili | |
dc.subject.yso | elektronit | |
dc.subject.yso | halogeenit | |
dc.subject.yso | ionit | |
dc.format.content | fulltext | |
jyx.subject.uri | http://www.yso.fi/onto/yso/p138 | |
jyx.subject.uri | http://www.yso.fi/onto/yso/p4030 | |
jyx.subject.uri | http://www.yso.fi/onto/yso/p4164 | |
jyx.subject.uri | http://www.yso.fi/onto/yso/p9015 | |
dc.rights.url | https://creativecommons.org/licenses/by/4.0/ | |
dc.relation.doi | 10.1021/jacs.8b09367 | |
dc.type.okm | A1 | |