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Progress in the Chemistry of Organic Natural Products 105 pp 137–215Cite as

A Critical Evaluation of the Quality of Published 13C NMR Data in Natural Product Chemistry

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Part of the book series: Progress in the Chemistry of Organic Natural Products ((POGRCHEM,volume 105))

Abstract

Nuclear Magnetic Resonance spectroscopy contributes very efficiently to the structure elucidation process in organic chemistry. Carbon-13 NMR spectroscopy allows direct insight into the skeleton of organic compounds and therefore plays a central role in the structural assignment of natural products. Despite this important contribution, there is no established and well-accepted workflow protocol utilized during the first steps of interpreting spectroscopic data and converting them into structural fragments and then combining them, by considering the given spectroscopic constraints, into a final proposal of structure. The so-called “combinatorial explosion” in the process of structure generation allows in many cases the generation of reasonable alternatives, which are usually ignored during manual interpretation of the measured data leading ultimately to a large number of structural revisions. Furthermore, even when the determined structure is correct, problems may exist such as assignment errors, ignoring chemical shift values, or assigning lines of impurities to the compound under consideration. An extremely large heterogeneity in the presentation of carbon NMR data can be observed, but, as a result of the efficiency and precision of spectrum prediction, the published data can be analyzed in substantial detail.

This contribution presents a comprehensive analysis of frequently occurring errors with respect to 13C NMR spectroscopic data and proposes a straightforward protocol to eliminate a high percentage of the most obvious errors. The procedure discussed can be integrated readily into the processes of submission and peer-reviewing of manuscripts.

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Authors and Affiliations

  1. Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090, Vienna, Austria

    Wolfgang Robien

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  1. Wolfgang Robien
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Correspondence to Wolfgang Robien .

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  1. Division of Medicinal Chemistry & Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, Ohio, USA

    A. Douglas Kinghorn

  2. Institute of Organic Chemistry, Johannes Kepler University Linz, Linz, Austria

    Heinz Falk

  3. Research Department of Pharmaceutical and Biological Chemistry, UCL School of Pharmacy, London, United Kingdom

    Simon Gibbons

  4. Graduate School of Pharmaceutical Science, Hokkaido University, Sapporo, Japan

    Jun'ichi Kobayashi

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Robien, W. (2017). A Critical Evaluation of the Quality of Published 13C NMR Data in Natural Product Chemistry. In: Kinghorn, A., Falk, H., Gibbons, S., Kobayashi, J. (eds) Progress in the Chemistry of Organic Natural Products 105. Progress in the Chemistry of Organic Natural Products, vol 105. Springer, Cham. https://doi.org/10.1007/978-3-319-49712-9_3

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