Interaction of the transition state of the Claisen rearrangement with surface of carbon nanotubes to predict catalytic activity

[Display omitted] •The transition state of possible mechanism of the allylphenyl ether Claisen rearrangement is calculated;•The cyclic transition state of the Claisen rearrangement is best stabilized on the surface of carbon nanotubes of a certain diameter;•Prediction of the catalytic activity of ca...

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Bibliographic Details
Published in:Computational and theoretical chemistry 2023-10, Vol.1228, p.114291, Article 114291
Main Authors: Vakulin, Ivan, Talipov, Rifkat, Fattakhov, Albert, Chernova, Daria
Format: Article
Language:English
Subjects:
Allylphenyl ether
Carbon nanotubes
Catalysis
Claisen rearrangement
MP2/6-31G(d,p)
Transition state
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Summary:[Display omitted] •The transition state of possible mechanism of the allylphenyl ether Claisen rearrangement is calculated;•The cyclic transition state of the Claisen rearrangement is best stabilized on the surface of carbon nanotubes of a certain diameter;•Prediction of the catalytic activity of carbon nanotubes in the Claisen rearrangement can be performed by using the concept of TSSS. The possibility of using the transition state shape selectivity concept for control of selectivity of reaction was previously demonstrated by us using the example of 1,3-dioxanes formation by Prins reaction. The extension of the applied approach to other reactions is of theoretical and practical interest. The aim of our work was to study the interaction of the frozen transition state of Claisen rearrangement with the surface of nanotubes of various structures to predict their catalytic activity. Claisen rearrangement of allylphenyl ether was chosen as a model reaction, and carbon nanotubes with different diameters were chosen as a porous materials. The calculated dependence of the stabilization energy on the nanotube diameter has an extreme character with pronounced maxima at a diameter of 10.2–10.4 Å. The obtained results allow to predict the catalytic activity of nanotubes with a diameter of 10–11 Å in Claisen rearrangement of allylphenyl ether.
ISSN:2210-271X
DOI:10.1016/j.comptc.2023.114291