Looking into the Dynamics of Molecular Crystals of Ibuprofen and Terephthalic Acid Using O and H Nuclear Magnetic Resonance Analyses

Overview

Journal Magn Reson Chem

Specialty Chemistry

Date 2021 Feb 22

PMID 33615550

Citations 4

Authors

Chia-Hsin Chen

Ieva Goldberga

Philippe Gaveau

Sebastien Mittelette

Jessica Spackova

Chuck Mullen

Ivan Petit

Thomas-Xavier Metro

Bruno Alonso

Christel Gervais

Danielle Laurencin

Affiliations

Soon will be listed here.

Abstract

Oxygen-17 and deuterium are two quadrupolar nuclei that are of interest for studying the structure and dynamics of materials by solid-state nuclear magnetic resonance (NMR). Here, O and H NMR analyses of crystalline ibuprofen and terephthalic acid are reported. First, improved O-labelling protocols of these molecules are described using mechanochemistry. Then, dynamics occurring around the carboxylic groups of ibuprofen are studied considering variable temperature O and H NMR data, as well as computational modelling (including molecular dynamics simulations). More specifically, motions related to the concerted double proton jump and the 180° flip of the H-bonded (-COOH) unit in the crystal structure were looked into, and it was found that the merging of the C=O and C-OH O resonances at high temperatures cannot be explained by the sole presence of one of these motions. Lastly, preliminary experiments were performed with a H- O diplexer connected to the probe. Such configurations can allow, among others, H and O NMR spectra to be recorded at different temperatures without needing to tune or to change probe configurations. Overall, this work offers a few leads which could be of use in future studies of other materials using O and H NMR.

Citing Articles

O NMR Spectroscopy Reveals CO Speciation and Dynamics in Hydroxide-Based Carbon Capture Materials.

Rhodes B, Schaaf L, Zick M, Pugh S, Hilliard J, Sharma S Chemphyschem. 2024; 26(5):e202400941.

PMID: 39565330 PMC: 11878753. DOI: 10.1002/cphc.202400941.

Temperature-induced mobility in octacalcium phosphate impacts crystal symmetry: water dynamics studied by NMR crystallography.

Nelson A, Papawassiliou W, Paul S, Hediger S, Hung I, Gan Z Faraday Discuss. 2024; 255(0):451-482.

PMID: 39390961 PMC: 11710991. DOI: 10.1039/d4fd00108g.

H/O Chemical Shift Waves in Carboxyl-Bridged Hydrogen Bond Networks in Organic Solids.

Wu G, Dai Y, Hung I, Gan Z, Terskikh V J Phys Chem A. 2024; 128(21):4288-4296.

PMID: 38748612 PMC: 11840671. DOI: 10.1021/acs.jpca.4c01866.

First Direct Insight into the Local Environment and Dynamics of Water Molecules in the Whewellite Mineral Phase: Mechanochemical Isotopic Enrichment and High-Resolution O and H NMR Analyses.

Goldberga I, Patris N, Chen C, Thomassot E, Trebosc J, Hung I J Phys Chem C Nanomater Interfaces. 2022; 126(29):12044-12059.

PMID: 35928237 PMC: 9340807. DOI: 10.1021/acs.jpcc.2c02070.

Residue-Specific High-Resolution O Solid-State Nuclear Magnetic Resonance of Peptides: Multidimensional Indirect H Detection and Magic-Angle Spinning.

Hung I, Keeler E, Mao W, Gorkov P, Griffin R, Gan Z J Phys Chem Lett. 2022; 13(28):6549-6558.

PMID: 35830592 PMC: 9888599. DOI: 10.1021/acs.jpclett.2c01777.

References

Ishii Y, Wickramasinghe A, Matsuda I, Endo Y, Ishii Y, Nishiyama Y . Progress in proton-detected solid-state NMR (SSNMR): Super-fast 2D SSNMR collection for nano-mole-scale proteins. J Magn Reson. 2017; 286:99-109. PMC: 6387629. DOI: 10.1016/j.jmr.2017.11.011. View

Wu G, Hung I, Gan Z, Terskikh V, Kong X . Solid-State O NMR Study of Carboxylic Acid Dimers: Simultaneously Accessing Spectral Properties of Low- and High-Energy Tautomers. J Phys Chem A. 2019; 123(38):8243-8253. DOI: 10.1021/acs.jpca.9b07224. View

Schmidt J, Sebastiani D . Anomalous temperature dependence of nuclear quadrupole interactions in strongly hydrogen-bonded systems from first principles. J Chem Phys. 2005; 123(7):074501. DOI: 10.1063/1.2000241. View

Carignani E, Borsacchi S, Geppi M . Dynamics by solid-state NMR: detailed study of ibuprofen Na salt and comparison with ibuprofen. J Phys Chem A. 2011; 115(32):8783-90. DOI: 10.1021/jp202650n. View

Matlahov I, van der Wel P . Hidden motions and motion-induced invisibility: Dynamics-based spectral editing in solid-state NMR. Methods. 2018; 148:123-135. PMC: 6133742. DOI: 10.1016/j.ymeth.2018.04.015. View

Kolokolov D, Jobic H, Stepanov A, Guillerm V, Devic T, Serre C . Dynamics of benzene rings in MIL-53(Cr) and MIL-47(V) frameworks studied by 2H NMR spectroscopy. Angew Chem Int Ed Engl. 2010; 49(28):4791-4. DOI: 10.1002/anie.201001238. View

Beckham G, Peters B, Starbuck C, Variankaval N, Trout B . Surface-mediated nucleation in the solid-state polymorph transformation of terephthalic acid. J Am Chem Soc. 2007; 129(15):4714-23. DOI: 10.1021/ja0687567. View

Friscic T, Mottillo C, Titi H . Mechanochemistry for Synthesis. Angew Chem Int Ed Engl. 2019; 59(3):1018-1029. DOI: 10.1002/anie.201906755. View

Catalano J, Murphy A, Yao Y, Zumbulyadis N, Centeno S, Dybowski C . Molecular dynamics of palmitic acid and lead palmitate in cross-linked linseed oil films: Implications from deuterium magnetic resonance for lead soap formation in traditional oil paintings. Solid State Nucl Magn Reson. 2017; 89:21-26. DOI: 10.1016/j.ssnmr.2017.12.003. View

10.

Perras F, Venkatesh A, Hanrahan M, Goh T, Huang W, Rossini A . Indirect detection of infinite-speed MAS solid-state NMR spectra. J Magn Reson. 2017; 276:95-102. DOI: 10.1016/j.jmr.2017.01.010. View

11.

Mandala V, Williams J, Hong M . Structure and Dynamics of Membrane Proteins from Solid-State NMR. Annu Rev Biophys. 2018; 47:201-222. PMC: 6312106. DOI: 10.1146/annurev-biophys-070816-033712. View

12.

Wijesekara A, Venkatesh A, Lampkin B, VanVeller B, Lubach J, Nagapudi K . Fast Acquisition of Proton-Detected HETCOR Solid-State NMR Spectra of Quadrupolar Nuclei and Rapid Measurement of NH Bond Lengths by Frequency Selective HMQC and RESPDOR Pulse Sequences. Chemistry. 2020; 26(35):7881-7888. DOI: 10.1002/chem.202000390. View

13.

Goedecker , Teter , HUTTER . Separable dual-space Gaussian pseudopotentials. Phys Rev B Condens Matter. 1996; 54(3):1703-1710. DOI: 10.1103/physrevb.54.1703. View

14.

Dudognon E, Danede F, Descamps M, Correia N . Evidence for a new crystalline phase of racemic Ibuprofen. Pharm Res. 2008; 25(12):2853-8. DOI: 10.1007/s11095-008-9655-7. View

15.

Lilly Thankamony A, Wittmann J, Kaushik M, Corzilius B . Dynamic nuclear polarization for sensitivity enhancement in modern solid-state NMR. Prog Nucl Magn Reson Spectrosc. 2017; 102-103:120-195. DOI: 10.1016/j.pnmrs.2017.06.002. View

16.

Gan Z, Hung I, Wang X, Paulino J, Wu G, Litvak I . NMR spectroscopy up to 35.2T using a series-connected hybrid magnet. J Magn Reson. 2017; 284:125-136. PMC: 5675800. DOI: 10.1016/j.jmr.2017.08.007. View

17.

Pell A, Sanders K, Wegner S, Pintacuda G, Grey C . Low-power broadband solid-state MAS NMR of N. J Chem Phys. 2017; 146(19):194202. PMC: 5648583. DOI: 10.1063/1.4983220. View

18.

Grimme S, Antony J, Ehrlich S, Krieg H . A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu. J Chem Phys. 2010; 132(15):154104. DOI: 10.1063/1.3382344. View

19.

Geppi M, Guccione S, Mollica G, Pignatello R, Veracini C . Molecular properties of ibuprofen and its solid dispersions with Eudragit RL100 studied by solid-state nuclear magnetic resonance. Pharm Res. 2005; 22(9):1544-55. DOI: 10.1007/s11095-005-6249-5. View

20.

Wu G . O NMR studies of organic and biological molecules in aqueous solution and in the solid state. Prog Nucl Magn Reson Spectrosc. 2019; 114-115:135-191. DOI: 10.1016/j.pnmrs.2019.06.002. View