Synthesis and crystal structures of 2-(ferrocenylcarbonyl)benzoic acid and 3-ferrocenylphthalide
| Autor: | Jonathan T Bergeron, Uttam R. Pokharel, Frank R. Fronczek |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
crystal structure
Dimer 02 engineering and technology Crystal structure Dihedral angle 010402 general chemistry 01 natural sciences Research Communications Phthalide Crystal lcsh:Chemistry chemistry.chemical_compound General Materials Science 2-carboxybenzylferrocene Benzoic acid 3-ferrocenylphthalide Hydrogen bond redetermination General Chemistry 021001 nanoscience & nanotechnology Condensed Matter Physics zn reduction 0104 chemical sciences 2-(ferrocenylcarbonyl)benzoic acid Crystallography chemistry Ferrocene lcsh:QD1-999 2-(ferrocenylcarbonyl)benzoic acid 2-carboxybenzylferrocene 0210 nano-technology |
| Zdroj: | Acta Crystallographica Section E: Crystallographic Communications, Vol 76, Iss 7, Pp 1163-1167 (2020) Acta Crystallographica Section E: Crystallographic Communications |
| ISSN: | 2056-9890 |
| Popis: | 2-Ferrocenylcarbonylbenzoic acid (C18H14FeO3) was synthesized from the Friedel–Crafts acylation of ferrocene with phthalic anhydride, and the product was reduced to 3-ferrocenylphthalide (C18H14FeO2) using Zn(Cu) in aqueous sodium hydroxide. Both compounds were characterized using IR, NMR, and single-crystal X-ray analysis. The title compounds, 2-(ferrocenylcarbonyl)benzoic acid, [Fe(C5H5)(C13H9O3)], 1, and 3-ferrocenylphthalide [systematic name: 3-ferrocenyl-2-benzofuran-1(3H)-one], [Fe(C5H5)(C13H9O2)], 2, have been synthesized and structurally characterized by single-crystal X-ray diffraction. The crystal structure of compound 1 was solved recently at room temperature [Qin, Y. (2019 ▸). CSD Communication (CCDC deposition number 1912662). CCDC, Cambridge, England]. Here we report a redetermination of its crystal structure at 90 K with improved precision by a factor of about three. The molecular structures of both compounds exhibit a typical sandwich structure. In the crystal packing of compound 1, each molecule engages in intermolecular hydrogen bonding, forming a centrosymmetric dimer with graph-set notation R 2 2 (8) and an O⋯O distance of 2.6073 (15) Å. There are weak C—H⋯O and C—H⋯π interactions in the crystal packing of compound 2. The phthalide moiety in 2 is oriented roughly perpendicular to the ferrocene backbone, with a dihedral angle of 77.4 (2)°. |
| Databáze: | OpenAIRE |
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