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
dc.contributor.author | Pipim, George Baffour | |
dc.contributor.author | Opoku, Ernest | |
dc.contributor.author | Tia, Richard | |
dc.contributor.author | Adei, Evans | |
dc.date.accessioned | 2020-07-08T11:28:44Z | |
dc.date.accessioned | 2023-04-19T02:06:15Z | |
dc.date.available | 2020-07-08T11:28:44Z | |
dc.date.available | 2023-04-19T02:06:15Z | |
dc.date.issued | 2020-01-21 | |
dc.description | An article published by Elsevier Inc. and also available at https://doi.org/10.1016/j.jmgm.2020.107542 | en_US |
dc.description.abstract | The 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.sponsorship | KNUST | en_US |
dc.identifier.citation | G.B. Pipim et al. / Journal of Molecular Graphics and Modelling 97 (2020) 107542. https://doi.org/10.1016/j.jmgm.2020.107542 | en_US |
dc.identifier.uri | https://ir.knust.edu.gh/handle/123456789/12657 | |
dc.language.iso | en | en_US |
dc.publisher | Elsevier Inc. | en_US |
dc.subject | Density functional theory | en_US |
dc.subject | 1,3-Dipole | en_US |
dc.subject | Dipolarophile | en_US |
dc.subject | 4-Methylene-1,3-oxazol-5(4H)-One | en_US |
dc.subject | Spirocycloadduct | en_US |
dc.title | 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 | en_US |
dc.type | Article | en_US |
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