Details

Autor(en) / Beteiligte

• Mikhova, B.
• Stamboliyska, B.
• Koch, A.
• Duddeck, H.
• Kleinpeter, E.

Titel

DFT-GIAO-NBO and 13C NMR study of the δ-syn-axial effect in 2,4-disubstituted adamantanes

Ist Teil von

• Magnetic resonance in chemistry, 2008-12, Vol.46 (12), p.1153-1157

Ort / Verlag

Chichester, UK: John Wiley & Sons, Ltd

Erscheinungsjahr

2008

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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 δ‐syn‐axial positions showed the largest overall deshielding, i.e. the sum of all 13C chemical shifts [Σδ(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 δ‐syn‐axial effect. Copyright © 2008 John Wiley & Sons, Ltd.