X-Ray Diffraction and Theoretical Calculation–Supported Formation of Polymorphic Cocrystals Discovered Through Thermal Methods: A Case Study
| Autor: | Monica Calatayud, Julia Contreras-García, Zhengzheng Zhou, Henry H.Y. Tong, Liang Li, Ying Zheng |
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| Přispěvatelé: | Southern Medical University [Guangzhou], Laboratoire de chimie théorique (LCT), Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Sun Yat-Sen University [Guangzhou] (SYSU), Macao Polytechnic Institute [Macao], University of Macau (UMac) |
| Rok vydání: | 2019 |
| Předmět: |
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Molecular Materials science salicylic acid Pharmaceutical Science 02 engineering and technology Crystallography X-Ray 030226 pharmacology & pharmacy Cocrystal polymorphism 03 medical and health sciences symbols.namesake density functional theory (DFT) 0302 clinical medicine X-Ray Diffraction [CHIM.CRIS]Chemical Sciences/Cristallography Non-covalent interactions Molecule cocrystal Thermal analysis chemistry.chemical_classification Calorimetry Differential Scanning Hydrogen Bonding [SDV.SP]Life Sciences [q-bio]/Pharmaceutical sciences 021001 nanoscience & nanotechnology Benzamidines thermal methods [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry Solubility chemistry Polymorphism (materials science) Chemical physics X-ray crystallography modulated temperature DSC (MTDSC) symbols Density functional theory van der Waals force Crystallization 0210 nano-technology Powder Diffraction |
| Zdroj: | Journal of Pharmaceutical Sciences Journal of Pharmaceutical Sciences, Wiley, In press, ⟨10.1016/j.xphs.2019.05.019⟩ |
| ISSN: | 0022-3549 1520-6017 |
| Popis: | International audience; Polymorphism commonly exists in the preparation of cocrystals and has attracted widespread attention from both the pharmaceutical industry and academia. However, few studies have examined how to discover polymorphic cocrystals and their potential formation mechanism. In this study, we report the novel discovery of salicylic acid: 3-nitrobenzamide (SA-3NBZ) polymorphic cocrystals by thermal methods. The formation mechanism is elucidated based on theoretical calculations. SA-3NBZ polymorphic cocrystals with molar ratio of 1:1 and 2:2 were discovered using the combination of differential scanning calorimetry and hot stage microscopy. Single-crystal X-ray diffraction analysis confirmed this discovery. Density functional theory calculations corrected with dispersion were conducted to illustrate the energetic stabilization of SA polymorphic cocrystals. Compared with the starting materials, formation of the cocrystals at 1:1 and 2:2 present a weak stabilization with overall energy reduction of −0.01 and −0.05 eV/molecule, respectively. The calculated noncovalent interactions index further suggests that intralayer hydrogen bonds and van der Waals forces contribute to these weak interactions. The density functional theory calculations are in good agreement with the X-ray diffraction data. Hence, thermal analysis is a simple and reliable method to discover polymorphic cocrystals. |
| Databáze: | OpenAIRE |
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