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1H and 13C NMR study of quaternary benzo[c]phenanthridine alkaloids

✍ Scribed by Radek Marek; Jaromír Toušek; Jiří Dostál; Jiří Slavík; Roger Dommisse; Vladimír Sklenář


Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
105 KB
Volume
37
Category
Article
ISSN
0749-1581

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✦ Synopsis


C and in some cases also 15 N chemical shifts of quaternary benzo[c]phenanthridine alkaloids (fagaronine, chelerythrine, chelilutine, chelirubine, nitidine, sanguilutine, sanguinarine, and sanguirubine) were systematically studied by NMR spectroscopy and ab initio calculations. The assignment of signals in the 1 H and 13 C NMR spectra was obtained from 2D NOE and gradient-enhanced single-quantum multiple bond correlation (GSQMBC) experiments. The ab initio geometry optimization using Gaussian 94 at the RHF/6-31 G ŁŁ level, followed by the calculation of chemical shielding using the deMon/NMR code at the IGLO II level, were carried out in order to rationalize the assignment of individual experimentally determined resonances.


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