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Magnetically Induced Alignment of Natural Products for Stereochemical Structure Determination via NMR
Author(s) -
Karschin Niels,
Wolkenstein Klaus,
Griesinger Christian
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202004881
Subject(s) - chemistry , molecule , residual dipolar coupling , density functional theory , yield (engineering) , residual , anisotropy , chemical physics , analyte , proton nmr , computational chemistry , polymer , dipole , materials science , organic chemistry , physics , algorithm , quantum mechanics , computer science , metallurgy
Anisotropic NMR has gained increasing popularity to determine the structure and specifically the configuration of small, flexible, non‐crystallizable molecules. However, it suffers from the necessity to dissolve the analyte in special media such as liquid crystals or polymer gels. Generally, small degrees of alignment are also caused by an anisotropic magnetic susceptibility of the molecule, for example, induced by aromatic moieties. For this mechanism, the alignment can be predicted via density functional theory. Here we show that both residual dipolar couplings and residual chemical shift anisotropies can be acquired from natural products without special sample preparation using magnetically induced alignment. On the two examples of the novel natural product gymnochrome G and the alkaloid strychnine, these data, together with the predicted alignment, yield the correct configuration with high certainty.