Modeling Decomposition of N-Nitrosoamides in a Self-Assembled Capsule.

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ID: 76716
2019
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Abstract
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.
Reference Key
brea2019modelingthe Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Brea, Oriana;Daver, Henrik;Rebek, Julius;Himo, Fahmi;
Journal The Journal of organic chemistry
Year 2019
DOI
10.1021/acs.joc.9b01034
URL
Keywords
Raman Spectroscopy supramolecular self-assembly halogen bonding resorcinarene reversible addition fragmentation chain transfer polymerization

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