Peri-, Chemo-, Regio-, Stereo- and Enantio-Selectivities of 1,3-dipolarcycloaddition reaction of C,N-Disubstituted nitrones withdisubstituted 4-methylene-1,3-oxazol-5(4H)- one: A quantummechanical study

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dc.contributor.authorPipim, George Baffour
dc.contributor.authorOpoku, Ernest
dc.contributor.authorTia, Richard
dc.contributor.authorAdei, Evans
dc.date.accessioned2020-07-08T11:28:44Z
dc.date.accessioned2023-04-19T02:06:15Z
dc.date.available2020-07-08T11:28:44Z
dc.date.available2023-04-19T02:06:15Z
dc.date.issued2020-01-21
dc.descriptionAn article published by Elsevier Inc. and also available at https://doi.org/10.1016/j.jmgm.2020.107542en_US
dc.description.abstractThe peri-, chemo-, regio-, stereo- and enantio-selectivities of 1,3-dipolar cycloaddition reaction of C,N-disubstituted nitrones with disubstituted 4-methylene-1,3-oxazol-5(4H)-one have been studied usingdensity functional theory (DFT) at the M06e2X/6-311G (d,p) level of theory. The 1,3-dipole preferentiallyadds chemo-selectively across the olefinic bond in a (3þ2) fashion forming the corresponding spi-rocycloadduct. The titled reaction occurs with poor enantio- and stereo-selectivities, but a high degree ofregio-selectivity is observed for the addition of the 1,3-dipole across the dipolarophile. Electron-withdrawing groups on the dipolarophile significantly reduce the activation barriers while electron-donating groups on the dipolarophile increase the activation barriers. Analysis of the HOMO andLUMO energies of the two reacting species indicates that the 1,3-dipole reacts as a nucleophile while thedipolarophile reacts as the electrophile. Investigation of the electrophilic Parr function (PþKÞat the variousreaction centers in the dipolarophile indicates that the 1,3-dipole selectively adds across the atomicspecies with the largest electrophilic Mulliken and NBO atomic spin densities which is in accordancewith the energetic trends observed.en_US
dc.description.sponsorshipKNUSTen_US
dc.identifier.citationG.B. Pipim et al. / Journal of Molecular Graphics and Modelling 97 (2020) 107542. https://doi.org/10.1016/j.jmgm.2020.107542en_US
dc.identifier.urihttps://ir.knust.edu.gh/handle/123456789/12657
dc.language.isoenen_US
dc.publisherElsevier Inc.en_US
dc.subjectDensity functional theoryen_US
dc.subject1,3-Dipoleen_US
dc.subjectDipolarophileen_US
dc.subject4-Methylene-1,3-oxazol-5(4H)-Oneen_US
dc.subjectSpirocycloadducten_US
dc.titlePeri-, Chemo-, Regio-, Stereo- and Enantio-Selectivities of 1,3-dipolarcycloaddition reaction of C,N-Disubstituted nitrones withdisubstituted 4-methylene-1,3-oxazol-5(4H)- one: A quantummechanical studyen_US
dc.typeArticleen_US
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