Modeling of the General Trends of Reactivity and Regioselectivity in Cyclopentadiene–Nitroalkene Diels–Alder Reactions
This study presents a theoretical investigation of the electronic properties of mono- and pentasubstituted cyclopentadiene analogs and variously substituted conjugated nitroalkenes bearing electron-donating and electron-withdrawing groups. Conceptual Density Functional Theory (CDFT) and Electron Loc...
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MDPI AG
2025-06-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/30/11/2467 |
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| author | Adrianna Fałowska Stanisław Grzybowski Daniel Kapuściński Karol Sambora Agnieszka Łapczuk |
| author_facet | Adrianna Fałowska Stanisław Grzybowski Daniel Kapuściński Karol Sambora Agnieszka Łapczuk |
| author_sort | Adrianna Fałowska |
| collection | DOAJ |
| description | This study presents a theoretical investigation of the electronic properties of mono- and pentasubstituted cyclopentadiene analogs and variously substituted conjugated nitroalkenes bearing electron-donating and electron-withdrawing groups. Conceptual Density Functional Theory (CDFT) and Electron Localization Function (ELF) analyses were employed to characterize the global and local reactivity indices of the reactants. The obtained data provided insights into the nucleophilic and electrophilic nature of the investigated systems, allowing for the prediction of their reactivity patterns in Diels–Alder reactions. A reactivity model for conjugated alkenes toward cyclopentadienes was developed based on correlation analysis using Hammett substituent constants. This approach enabled the prediction of reaction polarity in (4+2) cycloaddition processes, providing insight into how the electronic effects of substituents influence the reaction course. These findings contribute to a deeper understanding of structure–reactivity relationships in Diels–Alder processes. |
| format | Article |
| id | doaj-art-d6c824e77900437189c42e2c5d183689 |
| institution | Kabale University |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-d6c824e77900437189c42e2c5d1836892025-08-20T03:46:38ZengMDPI AGMolecules1420-30492025-06-013011246710.3390/molecules30112467Modeling of the General Trends of Reactivity and Regioselectivity in Cyclopentadiene–Nitroalkene Diels–Alder ReactionsAdrianna Fałowska0Stanisław Grzybowski1Daniel Kapuściński2Karol Sambora3Agnieszka Łapczuk4Department of Organic Chemistry and Technology, Cracow University of Technology, Warszawska 24, 31-155 Krakow, PolandDepartment of Organic Chemistry and Technology, Cracow University of Technology, Warszawska 24, 31-155 Krakow, PolandDepartment of Organic Chemistry and Technology, Cracow University of Technology, Warszawska 24, 31-155 Krakow, PolandDepartment of Organic Chemistry and Technology, Cracow University of Technology, Warszawska 24, 31-155 Krakow, PolandDepartment of Organic Chemistry and Technology, Cracow University of Technology, Warszawska 24, 31-155 Krakow, PolandThis study presents a theoretical investigation of the electronic properties of mono- and pentasubstituted cyclopentadiene analogs and variously substituted conjugated nitroalkenes bearing electron-donating and electron-withdrawing groups. Conceptual Density Functional Theory (CDFT) and Electron Localization Function (ELF) analyses were employed to characterize the global and local reactivity indices of the reactants. The obtained data provided insights into the nucleophilic and electrophilic nature of the investigated systems, allowing for the prediction of their reactivity patterns in Diels–Alder reactions. A reactivity model for conjugated alkenes toward cyclopentadienes was developed based on correlation analysis using Hammett substituent constants. This approach enabled the prediction of reaction polarity in (4+2) cycloaddition processes, providing insight into how the electronic effects of substituents influence the reaction course. These findings contribute to a deeper understanding of structure–reactivity relationships in Diels–Alder processes.https://www.mdpi.com/1420-3049/30/11/2467reactivity(4+2) cycloadditioncyclic dienesconjugated nitroalkenesCDFTMEDT |
| spellingShingle | Adrianna Fałowska Stanisław Grzybowski Daniel Kapuściński Karol Sambora Agnieszka Łapczuk Modeling of the General Trends of Reactivity and Regioselectivity in Cyclopentadiene–Nitroalkene Diels–Alder Reactions Molecules reactivity (4+2) cycloaddition cyclic dienes conjugated nitroalkenes CDFT MEDT |
| title | Modeling of the General Trends of Reactivity and Regioselectivity in Cyclopentadiene–Nitroalkene Diels–Alder Reactions |
| title_full | Modeling of the General Trends of Reactivity and Regioselectivity in Cyclopentadiene–Nitroalkene Diels–Alder Reactions |
| title_fullStr | Modeling of the General Trends of Reactivity and Regioselectivity in Cyclopentadiene–Nitroalkene Diels–Alder Reactions |
| title_full_unstemmed | Modeling of the General Trends of Reactivity and Regioselectivity in Cyclopentadiene–Nitroalkene Diels–Alder Reactions |
| title_short | Modeling of the General Trends of Reactivity and Regioselectivity in Cyclopentadiene–Nitroalkene Diels–Alder Reactions |
| title_sort | modeling of the general trends of reactivity and regioselectivity in cyclopentadiene nitroalkene diels alder reactions |
| topic | reactivity (4+2) cycloaddition cyclic dienes conjugated nitroalkenes CDFT MEDT |
| url | https://www.mdpi.com/1420-3049/30/11/2467 |
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