Regio- and Diastereoselectivity of 1,3-dipolar Cycloaddition Reaction Between Sugar-Derived Nitrile Oxides and trans-Ethylcinnamate: DFT and QTAIM Analysis
Oumayma Abdessadak, Mohammed Aziz Ajana, Tahar Lakhlifi, Mohammed Bouachrine
{"title":"Regio- and Diastereoselectivity of 1,3-dipolar Cycloaddition Reaction Between Sugar-Derived Nitrile Oxides and trans-Ethylcinnamate: DFT and QTAIM Analysis","authors":"Oumayma Abdessadak, Mohammed Aziz Ajana, Tahar Lakhlifi, Mohammed Bouachrine","doi":"10.1002/slct.202500071","DOIUrl":null,"url":null,"abstract":"<p>Various aspects of the 1,3-dipolar cycloaddition between sugar-derived nitrile oxides and <i>trans</i>-ethylcinnamate were analyzed using density functional theory. Frontier molecular orbitals reveal that the reaction follows normal electron demand, further supported by reactivity indices. Methyl cation/anion affinity was employed to demonstrate electron displacement. Topological parameters were analyzed at critical bond points, and non-covalent interaction gradient isosurfaces were used to analyze the nature of the newly forming α-bonds at transition state. Activation energy results align with experimental observations, demonstrating that the reaction is perfectly regioselective. However, electron density findings favor the opposite addition.</p>","PeriodicalId":146,"journal":{"name":"ChemistrySelect","volume":"10 10","pages":""},"PeriodicalIF":1.9000,"publicationDate":"2025-03-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"ChemistrySelect","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/slct.202500071","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
Various aspects of the 1,3-dipolar cycloaddition between sugar-derived nitrile oxides and trans-ethylcinnamate were analyzed using density functional theory. Frontier molecular orbitals reveal that the reaction follows normal electron demand, further supported by reactivity indices. Methyl cation/anion affinity was employed to demonstrate electron displacement. Topological parameters were analyzed at critical bond points, and non-covalent interaction gradient isosurfaces were used to analyze the nature of the newly forming α-bonds at transition state. Activation energy results align with experimental observations, demonstrating that the reaction is perfectly regioselective. However, electron density findings favor the opposite addition.
期刊介绍:
ChemistrySelect is the latest journal from ChemPubSoc Europe and Wiley-VCH. It offers researchers a quality society-owned journal in which to publish their work in all areas of chemistry. Manuscripts are evaluated by active researchers to ensure they add meaningfully to the scientific literature, and those accepted are processed quickly to ensure rapid online publication.