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Modeling Decomposition of N-Nitrosoamides in a Self-Assembled Capsule
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Number of Authors: 42019 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 84, no 11, p. 7354-7361Article in journal (Refereed) Published
Abstract [en]

Density functional theory calculations are employed to investigate the mechanism and energies of the decomposition of N-nitrosoamides in the presence of a resorcinarene-based self-assembled nanocapsule. From experiments, it is known that confinement in the capsule inhibits the thermal decomposition of these compounds. N-Nitrosoamides with both aromatic and aliphatic substituents are considered here and the calculations show that, for both kinds, binding to the capsule leads to a significant increase in the energy barrier of the rate-determining step, the 1,3 N -> O acyl transfer reaction. A distortion-interaction analysis is conducted to probe the reasons behind the inhibition of the reaction. In addition, we characterized hypothetical intermediates that might be involved in the formation of the decomposition products inside the capsule. Interestingly, it is found that the capsule stabilizes ion-pair species that are unstable in mesitylene solution. Finally, a possible explanation is proposed for the observed encapsulation of the decomposition product of only one of the substrates.

Place, publisher, year, edition, pages
2019. Vol. 84, no 11, p. 7354-7361
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-170856DOI: 10.1021/acs.joc.9b01034ISI: 000471212000074PubMedID: 31062978OAI: oai:DiVA.org:su-170856DiVA, id: diva2:1338778
Available from: 2019-07-24 Created: 2019-07-24 Last updated: 2019-07-24Bibliographically approved

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Brea, OrianaDaver, HenrikHimo, Fahmi
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