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Structural Elucidation with NMR Spectroscopy: Practical Strategies for Organic Chemists
Author(s) -
Kwan Eugene E.,
Huang Shaw G.
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700966
Subject(s) - chemistry , proton , nuclear magnetic resonance spectroscopy , molecule , computational chemistry , menthol , natural product , proton nmr , organic molecules , stereochemistry , organic chemistry , physics , quantum mechanics
Practical strategies for the structural elucidation of small organic molecules are described for typical organic chemists. The analysis of an unknown is divided into three stages. First, structural connectivity is deduced from through‐bond correlation experiments. Next, the relative stereochemistry is determined from NOE correlations and coupling constants (both proton–proton and proton–carbon). Finally, the proposed structure is verified by a careful inspection of all of the observed data. Tactics for the management of overlapping peaks, low sample concentrations, and high molecular weights are also described. This approach is illustrated by the step‐by‐step analyses of a simple test compound, menthol, and a complex polycyclic natural product, salvinorin A. Detailed procedures and sample data for menthol are provided as a practical tutorial. This will enable organic chemists to elucidate a wide range of complex structures by using modern NMR spectroscopic experiments.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)