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Efficient and Accurate Description of Diels‐Alder Reactions Using Density Functional Theory

Modeling chemical reactions using Quantum Chemistry is a widely used predictive strategy capable to complement experiments in order to understand the intrinsic mechanisms guiding the chemicals towards the most favorable reaction products. However, at this purpose, it is mandatory to use reliable and...

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Autores principales: Loco, Daniele, Chataigner, Isabelle, Piquemal, Jean‐Philip, Spezia, Riccardo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9796631/
https://www.ncbi.nlm.nih.gov/pubmed/35696652
http://dx.doi.org/10.1002/cphc.202200349
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author Loco, Daniele
Chataigner, Isabelle
Piquemal, Jean‐Philip
Spezia, Riccardo
author_facet Loco, Daniele
Chataigner, Isabelle
Piquemal, Jean‐Philip
Spezia, Riccardo
author_sort Loco, Daniele
collection PubMed
description Modeling chemical reactions using Quantum Chemistry is a widely used predictive strategy capable to complement experiments in order to understand the intrinsic mechanisms guiding the chemicals towards the most favorable reaction products. However, at this purpose, it is mandatory to use reliable and computationally tractable theoretical methods. In this work, we focus on six Diels‐Alder reactions of increasing complexity and perform an extensive benchmark of middle‐ to low‐cost computational approaches to predict the characteristic reactions energy barriers. We found that Density Functional Theory, using the ωB97XD, LC‐ωPBE, CAM−B3LYP, M11 and MN12SX functionals, with empirical dispersion corrections coupled to an affordable 6‐31G basis set, provides quality results for this class of reactions, at a small computational effort. Such efficient and reliable simulation protocol opens perspectives for hybrid QM/MM molecular dynamics simulations of Diels‐Alder reactions including explicit solvation.
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spelling pubmed-97966312022-12-30 Efficient and Accurate Description of Diels‐Alder Reactions Using Density Functional Theory Loco, Daniele Chataigner, Isabelle Piquemal, Jean‐Philip Spezia, Riccardo Chemphyschem Research Articles Modeling chemical reactions using Quantum Chemistry is a widely used predictive strategy capable to complement experiments in order to understand the intrinsic mechanisms guiding the chemicals towards the most favorable reaction products. However, at this purpose, it is mandatory to use reliable and computationally tractable theoretical methods. In this work, we focus on six Diels‐Alder reactions of increasing complexity and perform an extensive benchmark of middle‐ to low‐cost computational approaches to predict the characteristic reactions energy barriers. We found that Density Functional Theory, using the ωB97XD, LC‐ωPBE, CAM−B3LYP, M11 and MN12SX functionals, with empirical dispersion corrections coupled to an affordable 6‐31G basis set, provides quality results for this class of reactions, at a small computational effort. Such efficient and reliable simulation protocol opens perspectives for hybrid QM/MM molecular dynamics simulations of Diels‐Alder reactions including explicit solvation. John Wiley and Sons Inc. 2022-07-08 2022-09-16 /pmc/articles/PMC9796631/ /pubmed/35696652 http://dx.doi.org/10.1002/cphc.202200349 Text en © 2022 The Authors. ChemPhysChem published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ (https://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Research Articles
Loco, Daniele
Chataigner, Isabelle
Piquemal, Jean‐Philip
Spezia, Riccardo
Efficient and Accurate Description of Diels‐Alder Reactions Using Density Functional Theory
title Efficient and Accurate Description of Diels‐Alder Reactions Using Density Functional Theory
title_full Efficient and Accurate Description of Diels‐Alder Reactions Using Density Functional Theory
title_fullStr Efficient and Accurate Description of Diels‐Alder Reactions Using Density Functional Theory
title_full_unstemmed Efficient and Accurate Description of Diels‐Alder Reactions Using Density Functional Theory
title_short Efficient and Accurate Description of Diels‐Alder Reactions Using Density Functional Theory
title_sort efficient and accurate description of diels‐alder reactions using density functional theory
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9796631/
https://www.ncbi.nlm.nih.gov/pubmed/35696652
http://dx.doi.org/10.1002/cphc.202200349
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