Elucidating the structural isomerism of fluorescent strigolactone analogue CISA-1
European Journal of Organic Chemistry, cilt.2015, sa.6, ss.1211-1217, 2015 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 2015 Sayı: 6
- Basım Tarihi: 2015
- Doi Numarası: 10.1002/ejoc.201403457
- Dergi Adı: European Journal of Organic Chemistry
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Sayfa Sayıları: ss.1211-1217
- Anahtar Kelimeler: Atropisomerism, Configuration determination, Conformation analysis, Density functional calculations, Lactones
- Boğaziçi Üniversitesi Adresli: Evet
Özet
The synthesis of a new potent strigolactone analogue (CISA-1), resulting in the formation of two interconverting structural isomers, which could not be identified, was recently reported. In the present study, a combined computational and experimental approach is used to identify the exact nature of these structural isomers. Although standard experimental techniques could not be used to determine the identity of the isomers, chromatographic methods excluded E/Z isomerisation. Computational 1H NMR chemical shift values and DFT calculations on interconversion barriers strongly suggest that the CISA-1 isomers were interconverting (Z)-configured atropisomers.