Record link: 
http://hdl.handle.net/20.500.12708/139089
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Title: 
How the Lewis Base F⁻ Catalyzes the 1,3-Dipolar Cycloaddition between Carbon Dioxide and Nitrilimines
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Citation: 
Svatunek, D., Hansen, T., Houk, K. N., & Hamlin, T. A. (2021). How the Lewis Base F− Catalyzes the 1,3-Dipolar Cycloaddition between Carbon Dioxide and Nitrilimines. Journal of Organic Chemistry, 86(5), 4320–4325. https://doi.org/10.1021/acs.joc.0c02963
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Publisher DOI: 
10.1021/acs.joc.0c02963
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Publication Type: 
Article - Original Research Article
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Language: 
English
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Authors: 
Svatunek, Dennis 
Hansen, Thomas 
Houk, Kendall N. 
Hamlin, Trevor A. 
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Organisational Unit: 
E163-03-2 - Forschungsgruppe Molekulare Chemie und Chemische Biologie 
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Journal: 
Journal of Organic Chemistry 
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ISSN: 
0022-3263
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Date (published): 
5-Mar-2021
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Number of Pages: 
6
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Publisher: 
AMER CHEMICAL SOC
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Peer reviewed: 
Yes
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Keywords: 
Cycloadditions; Organic Chemistry; Computational organic chemistry
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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.
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Research Areas: 
außerhalb der gesamtuniversitären Forschungsschwerpunkte: 50%
Computational Materials Science: 50%
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Science Branch: 
Chemie
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