Mechanism(s) of thermal decomposition of N-Nitrosoamides: A density functional theory study
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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.
Original language | English |
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Journal | Tetrahedron |
Volume | 75 |
Issue number | 8 |
Pages (from-to) | 929-935 |
Number of pages | 7 |
ISSN | 0040-4020 |
DOIs | |
Publication status | Published - 22 Feb 2019 |
Externally published | Yes |
- Computational chemistry, Density functional theory, Nitrosoamides, Reaction mechanism, Transition state
Research areas
ID: 241045162