Journal
JOURNAL OF MOLECULAR STRUCTURE
Volume 1129, Issue -, Pages 325-332Publisher
ELSEVIER
DOI: 10.1016/j.molstruc.2016.09.009
Keywords
Ferrocenyl fragment; beta-diketone tautomers; Schiff base ligand
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Funding
- Fondo Nacional de Desarrollo Cientifico y Tecnologico FONDECYT (Chile) [1130640]
- Fondo de Equipamiento Cientifico y Tecnologico FONDEQUIP [EQM120095, EQM130154]
- Vicerrectoria de Investigacion y Estudios Avanzados, Pontificia Universidad Catolica de Valparaiso, Chile
- CONICYT (Chile)
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Ferrocenyl beta-cliketones compounds beta 3-4 were synthesised by Claisen condensation reaction between acetylferrocene and ethyl benzoate or 4-bromoethyl benzoate. We also synthesised four new Schiff base ligands L1-4 by condensation reaction between beta 1-4 and 2-picolylamine. Identities of all these compounds were confirmed by satisfactory elemental analysis, H-1 nuclear magnetic resonance (NMR) correlation and infrared (IR) spectroscopy. In addition, all these compounds were authenticated by a single crystal X-ray diffraction analysis. In solution, H-1 NMR spectra of beta 3 and beta 4 exhibit a mixture of keto:enol tautomer ratios of 12:88 and 8:92, respectively, calculated by the integration of the free cyclopentadienyl ring. In contrast, the proton NMR spectra of L1-4 showed only the keto-enamine tautomer displacements. In addition, decoupled C-13 NMR spectrum clearly confirmed the existence of these tautomers. These results are in accordance with X-ray crystallographic studies, in which the enol and keto-enamine forms were elucidated for beta-diketones and Schiff base ligands, respectively. (C) 2016 Published by Elsevier B.V.
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