Computational studies of Brønsted acid-catalyzed transannular cycloadditions of cycloalkenone hydrazones

The contribution to the energy barrier of a series of tethers in transannular cycloadditions of cycloalkenes with hydrazones has been computationally studied by using DFT. The Houk's distortion model has been employed to evaluate the influence of the tether in the cycloaddition reaction. That m...

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Autores principales: Pedrón, Manuel, Sendra, Jana, Ginés, Irene, Tejero, Tomás, Vicario, Jose L, Merino, Pedro
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2023
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10130903/
https://www.ncbi.nlm.nih.gov/pubmed/37123091
http://dx.doi.org/10.3762/bjoc.19.37
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author Pedrón, Manuel
Sendra, Jana
Ginés, Irene
Tejero, Tomás
Vicario, Jose L
Merino, Pedro
author_facet Pedrón, Manuel
Sendra, Jana
Ginés, Irene
Tejero, Tomás
Vicario, Jose L
Merino, Pedro
author_sort Pedrón, Manuel
collection PubMed
description The contribution to the energy barrier of a series of tethers in transannular cycloadditions of cycloalkenes with hydrazones has been computationally studied by using DFT. The Houk's distortion model has been employed to evaluate the influence of the tether in the cycloaddition reaction. That model has been extended to determine the contribution of each tether and, more importantly, the effect exerted between them. In addition to the distortion induced by the tethers, the entropy effects caused by them has also been studied. The analysis of the evolution of the electron localization function along the reaction revealed the highly concerted character of the reaction.
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spelling pubmed-101309032023-04-27 Computational studies of Brønsted acid-catalyzed transannular cycloadditions of cycloalkenone hydrazones Pedrón, Manuel Sendra, Jana Ginés, Irene Tejero, Tomás Vicario, Jose L Merino, Pedro Beilstein J Org Chem Full Research Paper The contribution to the energy barrier of a series of tethers in transannular cycloadditions of cycloalkenes with hydrazones has been computationally studied by using DFT. The Houk's distortion model has been employed to evaluate the influence of the tether in the cycloaddition reaction. That model has been extended to determine the contribution of each tether and, more importantly, the effect exerted between them. In addition to the distortion induced by the tethers, the entropy effects caused by them has also been studied. The analysis of the evolution of the electron localization function along the reaction revealed the highly concerted character of the reaction. Beilstein-Institut 2023-04-20 /pmc/articles/PMC10130903/ /pubmed/37123091 http://dx.doi.org/10.3762/bjoc.19.37 Text en Copyright © 2023, Pedrón et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Full Research Paper
Pedrón, Manuel
Sendra, Jana
Ginés, Irene
Tejero, Tomás
Vicario, Jose L
Merino, Pedro
Computational studies of Brønsted acid-catalyzed transannular cycloadditions of cycloalkenone hydrazones
title Computational studies of Brønsted acid-catalyzed transannular cycloadditions of cycloalkenone hydrazones
title_full Computational studies of Brønsted acid-catalyzed transannular cycloadditions of cycloalkenone hydrazones
title_fullStr Computational studies of Brønsted acid-catalyzed transannular cycloadditions of cycloalkenone hydrazones
title_full_unstemmed Computational studies of Brønsted acid-catalyzed transannular cycloadditions of cycloalkenone hydrazones
title_short Computational studies of Brønsted acid-catalyzed transannular cycloadditions of cycloalkenone hydrazones
title_sort computational studies of brønsted acid-catalyzed transannular cycloadditions of cycloalkenone hydrazones
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10130903/
https://www.ncbi.nlm.nih.gov/pubmed/37123091
http://dx.doi.org/10.3762/bjoc.19.37
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