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Modeling Decomposition of N-Nitrosoamides in a Self-Assembled Capsule
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Rekke forfattare: 42019 (engelsk)Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 84, nr 11, s. 7354-7361Artikkel i tidsskrift (Fagfellevurdert) 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.

sted, utgiver, år, opplag, sider
2019. Vol. 84, nr 11, s. 7354-7361
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URN: urn:nbn:se:su:diva-170856DOI: 10.1021/acs.joc.9b01034ISI: 000471212000074PubMedID: 31062978OAI: oai:DiVA.org:su-170856DiVA, id: diva2:1338778
Tilgjengelig fra: 2019-07-24 Laget: 2019-07-24 Sist oppdatert: 2019-07-24bibliografisk kontrollert

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