TY - JOUR
T1 - Polarizable organometallic hydrazone chromophores. X-ray crystal structures of [(η5-C5H5) Fe(η5-C5H4)-C(p-MeC6 H4)=NNH-(η6-p-MeC6H4) Fe(η5-C5H5)]+PF 6 -, and of its toluoylferrocene precursor
AU - Figueroa, Walter
AU - Fuentealba, Mauricio
AU - Manzur, Carolina
AU - Vega, Andrés I.
AU - Carrillo, David
AU - Hamon, Jean René
N1 - Funding Information:
We thank the financial support from Fondo Nacional de Desarrollo Científico y Tecnológico, FONDECYT (Chile), Grant No. 1010318 (D.C., C.M.), the CNRS-CONICYT Project No. 16771 (D.C., C.M., J.-R.H.), and the Vicerrectoría de Investigación y Estudios Avanzados, Pontificia Universidad Católica de Valparaíso, Chile.
PY - 2005/8
Y1 - 2005/8
N2 - The homobimetallic hydrazone complex [CpFe(η6-p-CH 3C6H4)NHN=C(C6H4 -p-CH3)(η5-C5H4) FeCp]+PF6 - (2) (Cp = η5 -C5H5) is stereoselectively formed by reaction of the organometallic hydrazine precursor [CpFe(η6-p-CH 3C6H4-NHNH2)]+ PF6 - with the sterically demanding p-toluoylferrocene CpFe(η5-C5H4 )CO(C6H4-p-CH3) (1) in refluxing ethanol. Compound 2 has been fully characterized by IR, UV-vis, and 1H NMR spectroscopy, cyclic voltammetry and by an X-ray diffraction analysis. The most striking features of the crystal structure are the syn-conformation of the two organometallic units, the long Fe-Cipso bond distances and the slight cyclohexadienyl character at the coordinated C6 ring with a folding angle of 6.1°, and that coordinated C6- and C5-rings of the binucleating ligand are almost coplanar with a dihedral angle of 8.1°. The crystal structure of the p-toluoylferrocene 1 is also presented.
AB - The homobimetallic hydrazone complex [CpFe(η6-p-CH 3C6H4)NHN=C(C6H4 -p-CH3)(η5-C5H4) FeCp]+PF6 - (2) (Cp = η5 -C5H5) is stereoselectively formed by reaction of the organometallic hydrazine precursor [CpFe(η6-p-CH 3C6H4-NHNH2)]+ PF6 - with the sterically demanding p-toluoylferrocene CpFe(η5-C5H4 )CO(C6H4-p-CH3) (1) in refluxing ethanol. Compound 2 has been fully characterized by IR, UV-vis, and 1H NMR spectroscopy, cyclic voltammetry and by an X-ray diffraction analysis. The most striking features of the crystal structure are the syn-conformation of the two organometallic units, the long Fe-Cipso bond distances and the slight cyclohexadienyl character at the coordinated C6 ring with a folding angle of 6.1°, and that coordinated C6- and C5-rings of the binucleating ligand are almost coplanar with a dihedral angle of 8.1°. The crystal structure of the p-toluoylferrocene 1 is also presented.
KW - Dipolar chromophores
KW - Ferrocene complexes
KW - Organoiron complexes
KW - Organometallic hydrazone complexes
KW - Push-pull complexes
KW - X-ray structure
UR - http://www.scopus.com/inward/record.url?scp=21144444385&partnerID=8YFLogxK
U2 - 10.1016/j.crci.2004.11.035
DO - 10.1016/j.crci.2004.11.035
M3 - Article
AN - SCOPUS:21144444385
VL - 8
SP - 1268
EP - 1275
JO - Comptes Rendus Chimie
JF - Comptes Rendus Chimie
SN - 1631-0748
IS - 8 SPEC. ISS.
ER -