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Updated: Feb 28, 2026
Atomic Scale Structural Studies of Macromolecular Assemblies by Solid-state Nuclear Magnetic Resonance Spectroscopy
Published on: September 17, 2017
Application of Computational Chemical Shift Prediction Techniques to the Cereoanhydride Structure Problem-Carboxylate
Carla M Saunders1, Dean J Tantillo2
1Department of Chemistry, University of California-Davis, 1 Shields Avenue, Davis, CA 95616, USA. cmsaunders@ucdavis.edu.
Abstract:
Despite the vast array of techniques available to modern-day chemists, structural misassignments still occur. These misassignments are often only realized upon attempted synthesis, when the spectra of synthesized products do not match previously reported spectra. This was the case with marine natural product cereoanhydride. The originally proposed 7-membered ring anhydride (1) was shown to be incorrect, although a likely precursor to the correct structure (2) in both its laboratory synthesis and biosynthesis. Herein, in addition to showing how NMR computations could have been used to arrive at the correct structure, we show that the conversion of 1 to 2 is indeed energetically viable, and we highlight complications in predicting NMR chemical shifts for molecules with acidic protons.
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