Recurrent π-π stacking motifs in three new 4,5-dihydropyrazolyl-thiazole-coumarin hybrids: X-ray characterization, Hirshfeld surface analysis and DFT calculations
The synthesis and X-ray characterization of three new 4,5-dihydropyrazolylthiazole-coumarin hybrids (1-3) are reported herein, namely 3-(2-(3,5-bis(4-chlorophenyl)-4,5-dihydropyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one (1), 3-(2-(5-(4-chlorophenyl)-4,5-dihydro-3-phenylpyrazol-1-yl)thiazol-4-yl)-2H-c...
| Autores: | , , , , , , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2020 |
| País: | Argentina |
| Institución: | Consejo Nacional de Investigaciones Científicas y Técnicas |
| Repositorio: | CONICET Digital (CONICET) |
| Idioma: | inglés |
| OAI Identifier: | oai:ri.conicet.gov.ar:11336/143346 |
| Acceso en línea: | http://hdl.handle.net/11336/143346 |
| Access Level: | acceso abierto |
| Palabra clave: | COUMARIN INTERMOLECULAR INTERACTIONS DFT HIRSHFELD SURFACES https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| Sumario: | The synthesis and X-ray characterization of three new 4,5-dihydropyrazolylthiazole-coumarin hybrids (1-3) are reported herein, namely 3-(2-(3,5-bis(4-chlorophenyl)-4,5-dihydropyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one (1), 3-(2-(5-(4-chlorophenyl)-4,5-dihydro-3-phenylpyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one (2) and 3-(2-(3-(4-chlorophenyl)-4,5-dihydro-5-p-tolylpyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one (3). A detailed structural analysis of the noncovalent interactions and their evaluation using Hirshfeld surface analysis is also reported, evidencing the importance of C-H⋯O and π-π interactions. Finally, DFT calculations along with the molecular electrostatic potential (MEP) and NCIplot index analysis have been used to evaluate those interactions energetically and to investigate the relative importance of two different π-stacking modes that are recurrent binding motifs in the solid state architecture of the three complexes. |
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