The Role of Weak C–H···X (X = O, π) Interactions in Three 1-Hydroxy-2-naphthoic Acid Cocrystals with N-Containing Heteroaromatics: Structural Characterization and Synthon Cooperation
Herein, three novel cocrystals of 1-hydroxy-2-naphthoic acid: tetramethylpyrazine, 1-hydroxy-2-naphthoic acid:1,10-phenanthroline, and 1-hydroxy-2-naphthoic acid:1,4-bis(imidazol-1-ylmethyl)benzene (L2) were obtained by crystallization in methanol–water mixed solvent via a slow evaporation method. T...
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MDPI AG
2023-02-01
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| Series: | Crystals |
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| Online Access: | https://www.mdpi.com/2073-4352/13/3/402 |
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| author | Huiqi Qu Ruixin Chen Yiru Ma Na Li Mingjuan Zhang Yueqin Yu Zhiguo Lv Kang Liu |
| author_facet | Huiqi Qu Ruixin Chen Yiru Ma Na Li Mingjuan Zhang Yueqin Yu Zhiguo Lv Kang Liu |
| author_sort | Huiqi Qu |
| collection | DOAJ |
| description | Herein, three novel cocrystals of 1-hydroxy-2-naphthoic acid: tetramethylpyrazine, 1-hydroxy-2-naphthoic acid:1,10-phenanthroline, and 1-hydroxy-2-naphthoic acid:1,4-bis(imidazol-1-ylmethyl)benzene (L2) were obtained by crystallization in methanol–water mixed solvent via a slow evaporation method. The cocrystalline products <b>1</b>−<b>3</b> were carried out by a range of techniques, including single-crystal X-ray diffraction, Fourier transform–infrared spectroscopy, elemental analysis, and thermogravimetric testing. We analyzed the crystal structures of the cocrystals <b>1</b>−<b>3</b> and found that weak interactions C–H···X (X = O or π) were of great importance in the process of self-assembly as well as strong and conventional hydrogen bonds (N–H···O, O–H···N, O–H···O), leading to a stable and diverse multidimensional supramolecular architecture. It is worth noting that a series of ring motifs with different sizes were explored in the crystal structures of the above complexes, such as R<sup>2</sup><sub>2</sub>(5), R<sup>2</sup><sub>2</sub>(7), R<sup>2</sup><sub>2</sub>(8), R<sup>2</sup><sub>3</sub>(13), R<sup>2</sup><sub>4</sub>(16), R<sup>4</sup><sub>4</sub>(16), R<sup>4</sup><sub>4</sub>(22), and so on. The classical and robust supramolecular synthon intermolecular bond between acid and pyridine (acid···pyridine) heterosynthon R<sup>2</sup><sub>2</sub>(7), commonly found in organic solids containing carboxylic acids with other N-containing heteroaromatics, was further demonstrated to be involved in the construction of the hydrogen-bond networks of cocrystal 1. The thermogravimetric technique used in this study proved that the mass losses of these three cocrystals were closely related to the strength of the hydrogen bonds in the package fraction. |
| first_indexed | 2024-03-11T06:43:04Z |
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| institution | Directory Open Access Journal |
| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-03-11T06:43:04Z |
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| spelling | doaj.art-b61cf79f3e09446a94ed89bd25d84abc2023-11-17T10:28:16ZengMDPI AGCrystals2073-43522023-02-0113340210.3390/cryst13030402The Role of Weak C–H···X (X = O, π) Interactions in Three 1-Hydroxy-2-naphthoic Acid Cocrystals with N-Containing Heteroaromatics: Structural Characterization and Synthon CooperationHuiqi Qu0Ruixin Chen1Yiru Ma2Na Li3Mingjuan Zhang4Yueqin Yu5Zhiguo Lv6Kang Liu7College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, ChinaDepartment of Mathematics, College of Mathematics and Physics, Qingdao University of Science and Technology, Qingdao 266061, ChinaKey Laboratory of Eco-Chemical Engineering, International Science and Technology Cooperation Base of Eco-Chemical Engineering and Green Manufacturing, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, ChinaKey Laboratory of Eco-Chemical Engineering, International Science and Technology Cooperation Base of Eco-Chemical Engineering and Green Manufacturing, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, ChinaKey Laboratory of Eco-Chemical Engineering, International Science and Technology Cooperation Base of Eco-Chemical Engineering and Green Manufacturing, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, ChinaKey Laboratory of Eco-Chemical Engineering, International Science and Technology Cooperation Base of Eco-Chemical Engineering and Green Manufacturing, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, ChinaCollege of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, ChinaKey Laboratory of Eco-Chemical Engineering, International Science and Technology Cooperation Base of Eco-Chemical Engineering and Green Manufacturing, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, ChinaHerein, three novel cocrystals of 1-hydroxy-2-naphthoic acid: tetramethylpyrazine, 1-hydroxy-2-naphthoic acid:1,10-phenanthroline, and 1-hydroxy-2-naphthoic acid:1,4-bis(imidazol-1-ylmethyl)benzene (L2) were obtained by crystallization in methanol–water mixed solvent via a slow evaporation method. The cocrystalline products <b>1</b>−<b>3</b> were carried out by a range of techniques, including single-crystal X-ray diffraction, Fourier transform–infrared spectroscopy, elemental analysis, and thermogravimetric testing. We analyzed the crystal structures of the cocrystals <b>1</b>−<b>3</b> and found that weak interactions C–H···X (X = O or π) were of great importance in the process of self-assembly as well as strong and conventional hydrogen bonds (N–H···O, O–H···N, O–H···O), leading to a stable and diverse multidimensional supramolecular architecture. It is worth noting that a series of ring motifs with different sizes were explored in the crystal structures of the above complexes, such as R<sup>2</sup><sub>2</sub>(5), R<sup>2</sup><sub>2</sub>(7), R<sup>2</sup><sub>2</sub>(8), R<sup>2</sup><sub>3</sub>(13), R<sup>2</sup><sub>4</sub>(16), R<sup>4</sup><sub>4</sub>(16), R<sup>4</sup><sub>4</sub>(22), and so on. The classical and robust supramolecular synthon intermolecular bond between acid and pyridine (acid···pyridine) heterosynthon R<sup>2</sup><sub>2</sub>(7), commonly found in organic solids containing carboxylic acids with other N-containing heteroaromatics, was further demonstrated to be involved in the construction of the hydrogen-bond networks of cocrystal 1. The thermogravimetric technique used in this study proved that the mass losses of these three cocrystals were closely related to the strength of the hydrogen bonds in the package fraction.https://www.mdpi.com/2073-4352/13/3/402cocrystalssupramoleculeself-assembly1-hydroxy-2-naphthoic acidsynthon |
| spellingShingle | Huiqi Qu Ruixin Chen Yiru Ma Na Li Mingjuan Zhang Yueqin Yu Zhiguo Lv Kang Liu The Role of Weak C–H···X (X = O, π) Interactions in Three 1-Hydroxy-2-naphthoic Acid Cocrystals with N-Containing Heteroaromatics: Structural Characterization and Synthon Cooperation Crystals cocrystals supramolecule self-assembly 1-hydroxy-2-naphthoic acid synthon |
| title | The Role of Weak C–H···X (X = O, π) Interactions in Three 1-Hydroxy-2-naphthoic Acid Cocrystals with N-Containing Heteroaromatics: Structural Characterization and Synthon Cooperation |
| title_full | The Role of Weak C–H···X (X = O, π) Interactions in Three 1-Hydroxy-2-naphthoic Acid Cocrystals with N-Containing Heteroaromatics: Structural Characterization and Synthon Cooperation |
| title_fullStr | The Role of Weak C–H···X (X = O, π) Interactions in Three 1-Hydroxy-2-naphthoic Acid Cocrystals with N-Containing Heteroaromatics: Structural Characterization and Synthon Cooperation |
| title_full_unstemmed | The Role of Weak C–H···X (X = O, π) Interactions in Three 1-Hydroxy-2-naphthoic Acid Cocrystals with N-Containing Heteroaromatics: Structural Characterization and Synthon Cooperation |
| title_short | The Role of Weak C–H···X (X = O, π) Interactions in Three 1-Hydroxy-2-naphthoic Acid Cocrystals with N-Containing Heteroaromatics: Structural Characterization and Synthon Cooperation |
| title_sort | role of weak c h···x x o π interactions in three 1 hydroxy 2 naphthoic acid cocrystals with n containing heteroaromatics structural characterization and synthon cooperation |
| topic | cocrystals supramolecule self-assembly 1-hydroxy-2-naphthoic acid synthon |
| url | https://www.mdpi.com/2073-4352/13/3/402 |
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