<div class="csl-bib-body">
<div class="csl-entry">Svatunek, D., Hansen, T., Houk, K. N., & Hamlin, T. A. (2021). How the Lewis Base F<sup>−</sup> Catalyzes the 1,3-Dipolar Cycloaddition between Carbon Dioxide and Nitrilimines. <i>Journal of Organic Chemistry</i>, <i>86</i>(5), 4320–4325. https://doi.org/10.1021/acs.joc.0c02963</div>
</div>
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dc.identifier.issn
0022-3263
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dc.identifier.uri
http://hdl.handle.net/20.500.12708/139089
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dc.description.abstract
The mechanism of the Lewis base F⁻ catalyzed 1,3-dipolar cycloaddition between CO₂ and nitrilimines is interrogated using DFT calculations. F⁻ activates the nitrilimine, not CO₂ as proposed in the literature, and imparts a significant rate enhancement for the cycloaddition. The origin of this catalysis is in the strength of the primary orbital interactions between the reactants. The Lewis base activated nitrilimine-F⁻ has high-lying filled FMOs. The smaller FMO-LUMO gap promotes a rapid nucleophilic attack and overall cycloaddition with CO₂.
en
dc.language.iso
en
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dc.publisher
AMER CHEMICAL SOC
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dc.relation.ispartof
Journal of Organic Chemistry
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dc.subject
Cycloadditions
en
dc.subject
Organic Chemistry
en
dc.subject
Computational organic chemistry
en
dc.title
How the Lewis Base F⁻ Catalyzes the 1,3-Dipolar Cycloaddition between Carbon Dioxide and Nitrilimines
en
dc.type
Artikel
de
dc.type
Article
en
dc.description.startpage
4320
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dc.description.endpage
4325
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dc.type.category
Original Research Article
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tuw.container.volume
86
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tuw.container.issue
5
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true
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tuw.peerreviewed
true
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wb.publication.intCoWork
International Co-publication
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X1
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C1
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außerhalb der gesamtuniversitären Forschungsschwerpunkte
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tuw.researchTopic.name
Computational Materials Science
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tuw.researchTopic.value
50
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tuw.researchTopic.value
50
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dcterms.isPartOf.title
Journal of Organic Chemistry
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tuw.publication.orgunit
E163-03-2 - Forschungsgruppe Molekulare Chemie und Chemische Biologie
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tuw.publisher.doi
10.1021/acs.joc.0c02963
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dc.identifier.eissn
1520-6904
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dc.description.numberOfPages
6
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tuw.author.orcid
0000-0003-1101-2376
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tuw.author.orcid
0000-0002-6291-1569
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0000-0002-8387-5261
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0000-0002-5128-1004
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wb.sciencebranch
Chemie
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wb.sciencebranch.oefos
1040
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wb.facultyfocus
Chemistry and Technology of Materials
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Chemistry and Technology of Materials
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wb.facultyfocus.faculty
E150
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no Fulltext
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research article
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en
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restricted
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http://purl.org/coar/resource_type/c_2df8fbb1
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E163-03-2 - Forschungsgruppe Molekulare Chemie und Chemische Biologie
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0000-0003-1101-2376
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E163-03 - Forschungsbereich Organische und Biologische Chemie