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Solid-State 1H, 13C, and 17O NMR Characterization of the Two Uncommon Polymorphs of Curcumin

Cite this: Cryst. Growth Des. 2020, 20, 11, 7484–7491
Publication Date (Web):October 14, 2020
https://doi.org/10.1021/acs.cgd.0c01164
Copyright © 2020 American Chemical Society
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Abstract

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Curcumin is known to exist in three polymorphs (forms I, II, and III) in the solid state. The most common polymorph of curcumin (form I) is monoclinic in the space group P2/n, whereas the other two uncommon forms are both orthorhombic with the space groups of Pca21 and Pbca for forms II and III, respectively. While crystal structures are known for all three polymorphs of curcumin, their solid-state NMR signatures are incomplete in the literature. In this study, we report a complete set of solid-state 1H, 13C, and 17O NMR data for form III of curcumin. In addition, we discovered that form III of curcumin prepared by repeated drying from methanol is not stable, which undergoes slow structural transition to form II in the solid state over a period of days at room temperature. As a result, we were able to obtain new solid-state 17O NMR data for form II of curcumin, which complements the existing solid-state 1H and 13C NMR data for this polymorph in the literature. We compare experimental NMR parameters with calculated values by the GIPAW DFT and dispersion corrected DFT-D2 methods. We found that while the computed 13C chemical shifts are generally in excellent agreement with experimental values, the quality of the computed 1H and 17O NMR chemical shifts is less satisfactory. This may imply that it is necessary to include the nuclear quantum effects in future quantum chemical calculations to account for potential proton tunneling and dynamics.

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The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.cgd.0c01164.

  • 1H MAS NMR spectra showing the conversion from form I to form III. Stability of form III crystals monitored by 13C CP/MAS NMR. 17O MAS spectrum of form III obtained at 21.1 T. Computational results from DFT-D2. A complete list of computed 1H and 13C chemical shifts. (PDF)

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Cited By

This article is cited by 5 publications.

  1. Valeria A. Stepanova, Andres Guerrero, Cullen Schull, Joshua Christensen, Claire Trudeau, Joshua Cook, Kyle Wolmutt, Jordan Blochwitz, Abdelrahman Ismail, Joseph K. West, Amelia M. Wheaton, Ilia A. Guzei, Bin Yao, Alena Kubatova. Hybrid Synthetic and Computational Study of an Optimized, Solvent-Free Approach to Curcuminoids. ACS Omega 2022, 7 (8) , 7257-7277. https://doi.org/10.1021/acsomega.1c07006
  2. Chia‐Hsin Chen, Ieva Goldberga, Philippe Gaveau, Sébastien Mittelette, Jessica Špačková, Chuck Mullen, Ivan Petit, Thomas‐Xavier Métro, Bruno Alonso, Christel Gervais, Danielle Laurencin. Looking into the dynamics of molecular crystals of ibuprofen and terephthalic acid using 17 O and 2 H nuclear magnetic resonance analyses. Magnetic Resonance in Chemistry 2021, 59 (9-10) , 975-990. https://doi.org/10.1002/mrc.5141
  3. Katia Rubini, Elisa Boanini, Silvia Parmeggiani, Adriana Bigi. Curcumin-Functionalized Gelatin Films: Antioxidant Materials with Modulated Physico-Chemical Properties. Polymers 2021, 13 (11) , 1824. https://doi.org/10.3390/polym13111824
  4. James Palmer, Gang Wu. Recent developments in 17O NMR studies of organic and biological molecules in the solid state. 2021, 1-46. https://doi.org/10.1016/bs.arnmr.2021.03.001
  5. Marta K. Dudek, Sławomir Kaźmierski, Marek J. Potrzebowski. Fast and very fast MAS solid state NMR studies of pharmaceuticals. 2021, 97-189. https://doi.org/10.1016/bs.arnmr.2021.02.002

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