Weak Interactions in Cocrystals of Isoniazid with Glycolic and Mandelic Acids
This work deals with the preparation of pyridine-3-carbohydrazide (isoniazid, inh) cocrystals with two α-hydroxycarboxylic acids. The interaction of glycolic acid (H<sub>2</sub>ga) or d,l-mandelic acid (H<sub>2</sub>ma) resulted in the formation of cocrystals or salts of comp...
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MDPI AG
2021-03-01
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| Series: | Crystals |
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| Online Access: | https://www.mdpi.com/2073-4352/11/4/328 |
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| author | Raquel Álvarez-Vidaurre Alfonso Castiñeiras Antonio Frontera Isabel García-Santos Diego M. Gil Josefa M. González-Pérez Juan Niclós-Gutiérrez Rocío Torres-Iglesias |
| author_facet | Raquel Álvarez-Vidaurre Alfonso Castiñeiras Antonio Frontera Isabel García-Santos Diego M. Gil Josefa M. González-Pérez Juan Niclós-Gutiérrez Rocío Torres-Iglesias |
| author_sort | Raquel Álvarez-Vidaurre |
| collection | DOAJ |
| description | This work deals with the preparation of pyridine-3-carbohydrazide (isoniazid, inh) cocrystals with two α-hydroxycarboxylic acids. The interaction of glycolic acid (H<sub>2</sub>ga) or d,l-mandelic acid (H<sub>2</sub>ma) resulted in the formation of cocrystals or salts of composition (inh)·(H<sub>2</sub>ga) (<b>1</b>) and [Hinh]<sup>+</sup>[Hma]<sup>–</sup>·(H<sub>2</sub>ma) (<b>2</b>) when reacted with isoniazid. An N′-(propan-2-ylidene)isonicotinic hydrazide hemihydrate, (pinh)·1/2(H<sub>2</sub>O) (<b>3</b>), was also prepared by condensation of isoniazid with acetone in the presence of glycolic acid. These prepared compounds were well characterized by elemental analysis, and spectroscopic methods, and their three-dimensional molecular structure was determined by single crystal X-ray crystallography. Hydrogen bonds involving the carboxylic acid occur consistently with the pyridine ring N atom of the isoniazid and its derivatives. The remaining hydrogen-bonding sites on the isoniazid backbone vary based on the steric influences of the derivative group. These are contrasted in each of the molecular systems. Finally, Hirshfeld surface analysis and Density-functional theory (DFT) calculations (including NCIplot and QTAIM analyses) have been performed to further characterize and rationalize the non-covalent interactions. |
| first_indexed | 2024-03-10T12:55:35Z |
| format | Article |
| id | doaj.art-db8a2c9db53842058fff4a8400afca01 |
| institution | Directory Open Access Journal |
| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-03-10T12:55:35Z |
| publishDate | 2021-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Crystals |
| spelling | doaj.art-db8a2c9db53842058fff4a8400afca012023-11-21T11:57:35ZengMDPI AGCrystals2073-43522021-03-0111432810.3390/cryst11040328Weak Interactions in Cocrystals of Isoniazid with Glycolic and Mandelic AcidsRaquel Álvarez-Vidaurre0Alfonso Castiñeiras1Antonio Frontera2Isabel García-Santos3Diego M. Gil4Josefa M. González-Pérez5Juan Niclós-Gutiérrez6Rocío Torres-Iglesias7Department of Inorganic Chemistry, Faculty of Pharmacy, University of Santiago de Compostela, 15782 Santiago de Compostela, SpainDepartment of Inorganic Chemistry, Faculty of Pharmacy, University of Santiago de Compostela, 15782 Santiago de Compostela, SpainDepartment of Química, Universitat de les Illes Balears, Crta. de Valldemossa km 7.5, 07122 Palma de Mallorca, SpainDepartment of Inorganic Chemistry, Faculty of Pharmacy, University of Santiago de Compostela, 15782 Santiago de Compostela, SpainINBIOFAL (CONICET – UNT), Instituto de Química Orgánica, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Ayacucho 471, T4000INI San Miguel de Tucumán, ArgentinaDepartment of Inorganic Chemistry, Faculty of Pharmacy, University of Granada, 18071 Granada, SpainDepartment of Inorganic Chemistry, Faculty of Pharmacy, University of Granada, 18071 Granada, SpainDepartment of Inorganic Chemistry, Faculty of Pharmacy, University of Santiago de Compostela, 15782 Santiago de Compostela, SpainThis work deals with the preparation of pyridine-3-carbohydrazide (isoniazid, inh) cocrystals with two α-hydroxycarboxylic acids. The interaction of glycolic acid (H<sub>2</sub>ga) or d,l-mandelic acid (H<sub>2</sub>ma) resulted in the formation of cocrystals or salts of composition (inh)·(H<sub>2</sub>ga) (<b>1</b>) and [Hinh]<sup>+</sup>[Hma]<sup>–</sup>·(H<sub>2</sub>ma) (<b>2</b>) when reacted with isoniazid. An N′-(propan-2-ylidene)isonicotinic hydrazide hemihydrate, (pinh)·1/2(H<sub>2</sub>O) (<b>3</b>), was also prepared by condensation of isoniazid with acetone in the presence of glycolic acid. These prepared compounds were well characterized by elemental analysis, and spectroscopic methods, and their three-dimensional molecular structure was determined by single crystal X-ray crystallography. Hydrogen bonds involving the carboxylic acid occur consistently with the pyridine ring N atom of the isoniazid and its derivatives. The remaining hydrogen-bonding sites on the isoniazid backbone vary based on the steric influences of the derivative group. These are contrasted in each of the molecular systems. Finally, Hirshfeld surface analysis and Density-functional theory (DFT) calculations (including NCIplot and QTAIM analyses) have been performed to further characterize and rationalize the non-covalent interactions.https://www.mdpi.com/2073-4352/11/4/328isoniazidcocrystalsglycolic acidDL-mandelic acidX-ray structureHirshfeld surface analysis |
| spellingShingle | Raquel Álvarez-Vidaurre Alfonso Castiñeiras Antonio Frontera Isabel García-Santos Diego M. Gil Josefa M. González-Pérez Juan Niclós-Gutiérrez Rocío Torres-Iglesias Weak Interactions in Cocrystals of Isoniazid with Glycolic and Mandelic Acids Crystals isoniazid cocrystals glycolic acid DL-mandelic acid X-ray structure Hirshfeld surface analysis |
| title | Weak Interactions in Cocrystals of Isoniazid with Glycolic and Mandelic Acids |
| title_full | Weak Interactions in Cocrystals of Isoniazid with Glycolic and Mandelic Acids |
| title_fullStr | Weak Interactions in Cocrystals of Isoniazid with Glycolic and Mandelic Acids |
| title_full_unstemmed | Weak Interactions in Cocrystals of Isoniazid with Glycolic and Mandelic Acids |
| title_short | Weak Interactions in Cocrystals of Isoniazid with Glycolic and Mandelic Acids |
| title_sort | weak interactions in cocrystals of isoniazid with glycolic and mandelic acids |
| topic | isoniazid cocrystals glycolic acid DL-mandelic acid X-ray structure Hirshfeld surface analysis |
| url | https://www.mdpi.com/2073-4352/11/4/328 |
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