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The 1 : 1 co-crystallization of enantiomers of an arene-tethered and ortho-metallated N-heterocyclic carbene ruthenium(II) half-sandwich complex: Synthesis, structural characterization and theoretical study

Autor(es) y otros:
Karabiyik, Hasan; Kilincarslan, Rafet; Aygün, Muhittin; Cetinkaya, Bekir; García-Granda, SantiagoAutoridad Uniovi
Palabra(s) clave:

Half-Sandwich Complex

Ortho-Metallation

Co-Crystallization

Non-Merohedral Twin

Dft-B3lyp/Lanl2dz

Asymmetric Synthons

Fecha de publicación:
2008
Versión del editor:
http://dx.doi.org/10.1016/j.solidstatesciences.2007.08.011
Citación:
Solid State Sciences, 10(1), p. 104-113 (2008); doi:10.1016/j.solidstatesciences.2007.08.011
Descripción física:
p. 104-113
Resumen:

The reaction of [RuCl2(p-cymene)]2 with in situ deprotonated NHC precursor 1,3-bis(biphenyl-2-yl)imidazolinium chloride was carried out in p-xylene at 140 °C to produce 2, in which the NHC moiety acts as a tridentate C,C′,C′′-ligand. The complex 2 was characterized by NMR spectroscopy and X-ray crystallographic study. Crystallographic analysis combined with computational study regarding the compound, 1-[η6-(2′-biphenyl)]-3-[2-phenyl-1,2-phenylene]imidazolidin-2-ylidenechlororuthenium(II), 2, reveals that its metal-centered enantiomers are co-crystallized in 1:1 ratio and NHC frame possessing a tridentate coordination mode consists of σ-donation of the carbene carbon, η6-arene tethering of terminal biaryl and η1-coordination of the biphenyl ring at 2-position. Enantiomers of the complex are packed as asymmetric dimers in solid state formed by C–H⋯Cl type weak H-bonds and C–H⋯π type interactions giving rise to asymmetric chains. Both interactions serve to stabilization of the extended structure.

The reaction of [RuCl2(p-cymene)]2 with in situ deprotonated NHC precursor 1,3-bis(biphenyl-2-yl)imidazolinium chloride was carried out in p-xylene at 140 °C to produce 2, in which the NHC moiety acts as a tridentate C,C′,C′′-ligand. The complex 2 was characterized by NMR spectroscopy and X-ray crystallographic study. Crystallographic analysis combined with computational study regarding the compound, 1-[η6-(2′-biphenyl)]-3-[2-phenyl-1,2-phenylene]imidazolidin-2-ylidenechlororuthenium(II), 2, reveals that its metal-centered enantiomers are co-crystallized in 1:1 ratio and NHC frame possessing a tridentate coordination mode consists of σ-donation of the carbene carbon, η6-arene tethering of terminal biaryl and η1-coordination of the biphenyl ring at 2-position. Enantiomers of the complex are packed as asymmetric dimers in solid state formed by C–H⋯Cl type weak H-bonds and C–H⋯π type interactions giving rise to asymmetric chains. Both interactions serve to stabilization of the extended structure.

URI:
http://hdl.handle.net/10651/9102
ISSN:
1293-2558
Otros identificadores:
1160
DOI:
10.1016/j.solidstatesciences.2007.08.011
Patrocinado por:

The authors thank TÜBİTAK (The Scientific and Technical Research Council of Turkey) and Dokuz Eylül University Research Fund (respective project numbers: 105T372 and 04.KB.FEN.100) for financial support of this work. In addition, financial support from Spanish Ministerio de Educacion y Ciencia (MAT2006-01997 and ‘Factoría de Cristalizacíon’ Consolider Ingenio 2010) is acknowledged.

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