Revised assignment of the  1 H NMR spectrum of the quinolizidine alkaloid lupinine | Zendy

Rycroft David S. | Zendy; Robins David J. | Zendy; Sadler Ian H. | Zendy

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Revised assignment of the 1 H NMR spectrum of the quinolizidine alkaloid lupinine

Author(s) -

Rycroft David S.,

Robins David J.,

Sadler Ian H.

Publication year - 1992

Publication title -

magnetic resonance in chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.483

H-Index - 72

eISSN - 1097-458X

pISSN - 0749-1581

DOI - 10.1002/mrc.1260301306

Subject(s) - homonuclear molecule , chemistry , quinolizidine , two dimensional nuclear magnetic resonance spectroscopy , nuclear overhauser effect , stereochemistry , alkaloid , nuclear magnetic resonance spectroscopy , nmr spectra database , proton nmr , spectral line , organic chemistry , molecule , physics , astronomy

The 1 H NMR spectrum of the quinolizidine alkaloid lupinine was studied at 200 and 600 MHz. A full assignment of the 1 H signals was achieved by application of a variety of NMR techniques, including homonuclear 1 H NOE difference, 2D δ H /δ H COSY and direct δ C /δ H correlation experiments. This results in some changes to the current literature assignments; particularly important is the conclusion that the chemical shift difference between the equatorial (β) and axial (α) protons at C‐9 is negative (−0.47 ppm) rather than positive. The currently accepted assignment of the 13 C NMR spectrum has been confirmed by independent, and more direct, means.

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