Molecular and solid state structure of the doubly-substituted b-diketone 3,3'-bis(ferrocenylmethyl)pentane-2,4-dione#
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GUILLERMO AHUMADA [1] ; THIERRY ROISNEL [2] ; JEAN-RENÉ HAMON [2] ; DAVID CARRILLO [1] ; CAROLINA MANZUR [1]
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[1] Pontificia Universidad Católica de Valparaíso
Pontificia Universidad Católica de Valparaíso
Valparaíso, Chile
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[2] Université de Rennes 1 CNRS Institut des Sciences Chimiques de Rennes
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- Localización: Journal of the Chilean Chemical Society (Boletín de la Sociedad Chilena de Química), ISSN-e 0717-6309, ISSN 0366-1644, Vol. 58, Nº. 4, 2013, págs. 1963-1966
- Idioma: inglés
- Enlaces
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Resumen
The ferrocene-containing β-diketone, 3-ferrocenylmethyl-pentane-2,4-dione 1, has been synthesized by reacting ferrocenyl methanol with acetylacetone in the presence of cerium(IV) ammonium nitrate as catalyst in C-C bond formation, and isolated as an orange oily product in 90% yield. The doubly-substituted 1,3-diketone, 3,3'-bis(ferrocenylmethyl)pentane-2,4-dione 2 was isolated as orange crystals in 79% yield, upon standing a dichloromethane solution of 1 at -30 °C for two weeks. Both complexes have been authenticated by spectroscopic methods, mass spectrometry, and cyclic voltammetry. In addition, the molecular identity and geometry of 2 has been confirmed by single-crystal X-ray diffraction analysis. In the crystal lattice, the molecules pack as dimers through C-H---O hydrogen bondings, where weaker C-H---p interactions link the dimeric units to form a chain structure.
