Unsymmetrical cyrhetrenyl and ferrocenyl azines derived from 5-nitrofurane: Synthesis,structural characterization and electrochemistry |
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Affiliation: | 1. Instituto de Química, Pontificia Universidad Católica de Valparaíso, Casilla 4059, Valparaíso, Chile;2. Departamento de Química Inorgánica y Analítica, Facultad de Ciencias Químicas y, Farmacéuticas, Universidad de Chile, Casilla 233, Santiago, Chile;3. Instituto de Ciencias de Materiales de Madrid, Consejo Superior de Investigaciones, Cientificas, Sor Juana Inés de la Cruz 3, 28049 Madrid, Spain |
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Abstract: | A new series of unsymmetrical cyrhetrenyl and ferrocenyl azines that were monosubstituted (η5-C5H4)–C(R) N–N CH(5-NO2–2-C4H2O)]M {with M Re(CO)3 and R H (1a) or R Me (1b); M Fe(η5-C5H5) and R H (2a) or R Me (2b)} and disubstituted Fe{(η5-C5H4)–C(Me) N–N CH(5-NO2–2-C4H2O)}2] (3a) were prepared by condensation reactions of the corresponding organometallic hydrazone (η5-C5H4)–C(R) N–NH2)]M with 5-nitro-2-furaldehyde. The 1H and 13C{1H} NMR spectra indicated that these compounds adopted an (E,E)-configuration about the ?C N ? bond and an s-trans conformation about the N1–N2 bond, and this result was confirmed by X-ray crystallographic analyses of 1a and 2b. The opposite electronic effects of the organometallic fragments correlate with the co-planarity of the (η5-C5H4)–C(R) N–N CH(5-NO2–2-C4H2O)] system, the reduction potential of the nitro group (E1/2) and the chemical shifts of the iminic carbons. |
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