Unsymmetrical cyrhetrenyl and ferrocenyl azines derived from 5-nitrofurane: Synthesis, structural characterization and electrochemistry

Johana Gómez, A. Hugo Klahn, MAURICIO DANIEL FUENTEALBA CARRASCO, Diego Sierra, Claudio Olea-Azar, Manuela E. Medina

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10 Scopus citations

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.

Original languageEnglish
Pages (from-to)204-206
Number of pages3
JournalInorganic Chemistry Communications
Volume61
DOIs
StatePublished - 1 Nov 2015

Keywords

  • Crystal structure
  • Cyclic voltammetry
  • Cyrhetrenyl azines
  • Ferrocenyl azines
  • Nitrofurane
  • NMR

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