DFT-GIAO-NBO and 13C NMR study of the delta-syn-axial effect in 2,4-disubstituted adamantanes
- Six groups of diastereomeric 2,4-disubstituted adamantanes were studied with DFT-GIAO-NBO (natural orbital analysis) methods. The calculated 13C chemical shifts reproduce well the experimental data. It was found that among all diastereomers, those bearing substituents in -syn-axial positions showed the largest overall deshielding, i.e. the sum of all 13C chemical shifts [;;(13C)] was the greatest and also had the highest delocalization contribution to the molecular energy evaluated with NBO. The higher delocalization energy is proposed to be the origin of the deshielding -syn-axial effect
| URL: | http://onlinelibrary.wiley.com/doi/10.1002/mrc.2333/pdf |
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| DOI: | https://doi.org/10.1002/Mrc.2333 |
| ISSN: | 0749-1581 |
| Further contributing person(s): | Bozhana Mikhova, Bistra A. Stamboliyska, Andreas Koch, Helmut Duddeck, Erich Kleinpeter |
| Publication type: | Article |
| Language: | English |
| Year of first publication: | 2008 |
| Publication year: | 2008 |
| Release date: | 2017/03/24 |
| Source: | Magnetic Resonance in Chemistry. - ISSN 0749-1581. - 46 (2008), 12, S. 1153 - 1157 |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| Peer review: | Referiert |
