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Mechanism(s) of thermal decomposition of N-Nitrosoamides: A density functional theory study
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0001-7803-5033
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Number of Authors: 42019 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 75, no 8, p. 929-935Article in journal (Refereed) Published
Abstract [en]

The thermal decomposition of N-nitrosoamides has experimentally been demonstrated to depend on several factors, such as temperature, solvent and the substituents on the substrate. Consequently, a number of reaction mechanisms have been proposed for this process in the literature. In this work, we present a comprehensive computational investigation in which we examine the detailed reaction mechanisms for two N-nitrosoamides (with aliphatic and aromatic substituents) in two different solvents (mesitylene and methanol). It is shown that the reaction mechanism can change dramatically with the nature of the substrate and the choice of solvent. Importantly, it is found that the polar solvent stabilizes ion-pairs that are unstable in the non-polar solvent, which can play a key role in the mechanism.

Place, publisher, year, edition, pages
2019. Vol. 75, no 8, p. 929-935
Keywords [en]
Nitrosoamides, Reaction mechanism, Density functional theory, Transition state, Computational chemistry
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-166696DOI: 10.1016/j.tet.2018.12.054ISI: 000458708500001OAI: oai:DiVA.org:su-166696DiVA, id: diva2:1297324
Available from: 2019-03-19 Created: 2019-03-19 Last updated: 2019-05-07Bibliographically approved

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Brea, OrianaDaver, HenrikHimo, Fahmi
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