Trapping of 1,2-cyclohexadiene: A DFT mechanistic study on thereaction of 1,2-cyclohexadiene with olefins and nitrones

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dc.contributor.authorBoafo, Emmanuel Amoah
dc.contributor.authorDarko, Kwabena
dc.contributor.authorAfriyie, Bright Aryeh
dc.contributor.authorTia, Richard
dc.contributor.authorAdei, Evans
dc.date.accessioned2020-07-08T10:52:04Z
dc.date.accessioned2023-04-19T02:05:14Z
dc.date.available2020-07-08T10:52:04Z
dc.date.available2023-04-19T02:05:14Z
dc.date.issued2018-02-13
dc.descriptionAn article published by Elsevier Inc and also available at https://doi.org/10.1016/j.jmgm.2018.02.003en_US
dc.description.abstractThe mechanistic aspects of cycloaddition reactions of 1,2-cyclohexadiene with olefins and nitrones havebeen investigated with DFT calculations. The results show that the cycloaddition reactions of 1,2-cyclohexadiene with olefins do not go through a concerted pathway (one-step mechanism) but rathera stepwise one involving the formation of a biradical intermediate which then closes to formfinalcycloadduct. Electron-withdrawing substituents on the 1,2-cyclohexadiene decrease the activation bar-rier of the biradical-forming step but increase the barrier of the product-forming step and productstability, while electron-donating substituents on the 1,2-cyclohexadiene increase the barriers for boththe biradical-forming step and the product-forming step but decrease the product stability. In the re-action of 1,2-cyclohexadiene with nitrones, the four pathways investigated have activation barrierswithin 1 kcal/mol of one another, the lowest being 10.45 kcal/mol and the highest 11.04 kcal/mol,indicating that these reactions are very unselective. Electron-withdrawing groups on the nitrone increasethe stability of the resulting products whereas electron-donating group on the nitrone decrease thestability of the resulting products. The [3þ2] cycloadduct proceeds to the formation of a more stableformal [5þ2] cycloadduct if a phenyl substituent is present on the nitrogen of the nitrone.en_US
dc.description.sponsorshipKNUSTen_US
dc.identifier.citationE.A. Boafo et al. / Journal of Molecular Graphics and Modelling 81 (2018) 1e13. Trapping of 1,2-cyclohexadiene: A DFT mechanistic study on thereaction of 1,2-cyclohexadiene with olefins and nitrones. https://doi.org/10.1016/j.jmgm.2018.02.003en_US
dc.identifier.urihttps://ir.knust.edu.gh/handle/123456789/12652
dc.language.isoenen_US
dc.publisherElsevier Incen_US
dc.titleTrapping of 1,2-cyclohexadiene: A DFT mechanistic study on thereaction of 1,2-cyclohexadiene with olefins and nitronesen_US
dc.typeArticleen_US
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