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• W1567640079 abstract "The electronic circular dichroism (ECD) spectra of two sesquiterpenoids (1 and 2) related to oplopanone, obtained from a methanolic extract of the plant Serphidium stenocephalum (Artemisia stenocephala), were measured and reproduced by means of time-dependent density functional theory (TDDFT) calculations, establishing their absolute configuration. The application of ketone octant rule for carbonyl n-π* ECD band to compounds 1 and 2, which include an acyclic carbonyl group, was critically assessed. The peculiar oplopanone skeleton makes a straightforward application of the octant rule impossible, because of the uncertainty related to the shape of the so-called third nodal surface separating front and back octants. The various group contributions to the carbonyl n-π* ECD band were estimated with TDDFT calculations on selected molecular models obtained by consecutive dissections from 1. Chirality 26:39–43, 2013. © 2013 Wiley Periodicals, Inc." @default.
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• W1567640079 date "2013-11-19" @default.
• W1567640079 modified "2023-10-16" @default.
• W1567640079 title "Absolute Configuration of Oplopanone Derivatives From<i>Serphidium stenocephalum</i>: ECD Spectra of Acyclic Ketones With Front-Octant Contributions" @default.
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• W1567640079 doi "https://doi.org/10.1002/chir.22263" @default.
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