Crystal structure, Hirshfeld surface analysis, interaction energy and DFT studies of 4-[(4-allyl-2-methoxyphenoxy)methyl]-1-(4-methoxyphenyl)-1H-1,2,3-triazole
| Autor: | Abdeljalil Aatif, Joel T. Mague, Karim Chkirate, Tuncer Hökelek, Mohamed Essaber, Nada Kheira Sebbar, Abdelmaoujoud Taia |
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| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
π-stacking
crystal structure 010405 organic chemistry Chemistry Hydrogen bond Stacking Substituent General Chemistry Crystal structure Dihedral angle 010402 general chemistry Condensed Matter Physics Ring (chemistry) hydrogen bonding 01 natural sciences 0104 chemical sciences Crystal lcsh:Chemistry Crystallography chemistry.chemical_compound triazole lcsh:QD1-999 c—h...π(ring) interaction General Materials Science Density functional theory |
| Zdroj: | Acta Crystallographica Section E: Crystallographic Communications, Vol 76, Iss 6, Pp 962-966 (2020) |
| ISSN: | 2056-9890 |
| Popis: | In the title molecule, C20H21N3O3, the allyl substituent is rotated out of the plane of its attached phenyl ring [torsion angle 100.66 (15)°]. In the crystal, C—HMthphn...OMthphn (Mthphn = methoxyphenyl) hydrogen bonds lead to the formation of (100) layers that are connected into a three-dimensional network by C—H...π(ring) interactions, together with π–π stacking interactions [centroid-to-centroid distance = 3.7318 (10) Å] between parallel phenyl rings. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H...H (48.7%) and H...C/C...H (23.3%) interactions. Computational chemistry reveals that the C—HMthphn...OMthphn hydrogen bond energy is 47.1 kJ mol−1. The theoretical structure, optimized by density functional theory (DFT) at the B3LYP/ 6–311 G(d,p) level, is compared with the experimentally determined molecular structure. The HOMO–LUMO behaviour was elucidated to determine the energy gap. |
| Databáze: | OpenAIRE |
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