Synthesis, characterization and crystal structure of the tridentate metalloligand formed from mono-condensation of ferrocenoylacetone and 1,2-phenylenediamine

Mauricio Fuentealba, Alexander Trujillo, Jean René Hamon, David Carrillo, Carolina Manzur

Research output: Contribution to journalArticlepeer-review

31 Scopus citations

Abstract

Reaction of the ferrocenoylacetone 1 with o-phenylenediamine in refluxing dry toluene affords the new air and thermally stable organometallic tridentate compound ("half unit") 2, which was isolated and characterized by elemental analysis, IR, UV-visible, 1H and 13C NMR spectroscopy and, in addition, authenticated by a single crystal X-ray diffraction analysis. In solution, the metalloligand 2 exists as a mixture of two tautomeric isomers: a keto-amine or enaminone form (60%), CpFe(η5-C5H4)-C(O)CH{double bond, long}C(CH3)N(H)-o-C6H4NH2 (Cp = η5-C5H5), and a keto-imine or iminone form (40%), CpFe(η5-C5H4)-C(O)CH2C(CH3)N-o-C6H4NH2, whereas only the enaminone form is found in the solid state. The structure of 2 is stabilized by a network of intra- and intermolecular hydrogen bonds involving N-H, NH2 and C{double bond, long}O groups.

Original languageEnglish
Pages (from-to)76-82
Number of pages7
JournalJournal of Molecular Structure
Volume881
Issue number1-3
DOIs
StatePublished - 18 Jun 2008
Externally publishedYes

Keywords

  • Crystal structure
  • Ferrocenoyl ketoamine
  • Half unit
  • Hemi-Schiff base
  • Tridentate ligand

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