TY - JOUR
T1 - Synthesis, characterization and crystal structure of the tridentate metalloligand formed from mono-condensation of ferrocenoylacetone and 1,2-phenylenediamine
AU - Fuentealba, Mauricio
AU - Trujillo, Alexander
AU - Hamon, Jean René
AU - Carrillo, David
AU - Manzur, Carolina
N1 - Funding Information:
The authors are indebted to Dr. S. Sinbandhit (CRMPO, Rennes) for invaluable assistance with the 2D NMR experiments. Financial support from the Fondo Nacional de Desarrollo Científico y Tecnológico [FONDECYT (Chile), Grant No. 1040851 (C. M. and D. C.)], the ECOS-SUD (France) - CONICYT (Chile) agreement No. C05E03 (C.M., D.C. and J.-R.H.), and the Vicerrectoría de Investigación y Estudios Avanzados, Pontificia Universidad Católica de Valparaíso, Chile (C.M. and D.C.), is gratefully acknowledged. M.F. and A.T. thank the CONICYT, Chile, for support of a graduate fellowship.
PY - 2008/6/18
Y1 - 2008/6/18
N2 - 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.
AB - 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.
KW - Crystal structure
KW - Ferrocenoyl ketoamine
KW - Half unit
KW - Hemi-Schiff base
KW - Tridentate ligand
UR - http://www.scopus.com/inward/record.url?scp=43449131813&partnerID=8YFLogxK
U2 - 10.1016/j.molstruc.2007.08.030
DO - 10.1016/j.molstruc.2007.08.030
M3 - Article
AN - SCOPUS:43449131813
SN - 0022-2860
VL - 881
SP - 76
EP - 82
JO - Journal of Molecular Structure
JF - Journal of Molecular Structure
IS - 1-3
ER -