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Ruthenium complexes of chelating amido-functionalized N-heterocyclic carbene ligands: Synthesis, structure and DFT studies

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Abstract

Synthesis, structure and density functional theory (DFT) studies of a series of new ruthenium complexes, [1-(R)-3-N-(benzylacetamido)imidazol-2-ylidene]RuCl(p-cymene) [R = Me (1c), i-Pr (2c), CH2Ph (3c); p-cymene = 4-i-propyltoluene] supported over N/O-functionalized N-heterocyclic carbene (NHC) ligands are reported. In particular, the ruthenium (1–3)c complexes were synthesized from the respective silver complexes, [1-(R)-3-N-(benzylacetamido)imidazol-2-ylidene]2Ag + Cl −  [R = Me (1b), i-Pr (2b), CH2Ph (3b)] by the treatment with [Ru(p-cymene)Cl2]2 in 65–76% yields. The molecular structures of (1–3)c revealed the chelation of the N-heterocylic carbene ligand through the carbene center and an amido sidearm of the ligand in all of the three complexes. The density functional theory studies on the ruthenium (1–3)c complexes indicated strong binding of the NHC ligand to the metal center as was observed from the deeply buried NHC-Ru σ-bonding molecular orbitals.

A series of ruthenium complexes (1–3)c stabilized by amido-functionalized N-heterocyclic carbene ligands have been successfully synthesized employing a transmetallation route from its silver analogs.

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Authors and Affiliations

  1. Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400076, India

    SACHIN KUMAR, ANANTHA NARAYANAN, MITTA NAGESWAR RAO & PRASENJIT GHOSH

  2. National Single Crystal X-ray Diffraction Facility, Indian Institute of Technology Bombay, Powai, Mumbai, 400076, India

    MOBIN M SHAIKH

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  1. SACHIN KUMAR
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  2. ANANTHA NARAYANAN
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KUMAR, S., NARAYANAN, A., RAO, M.N. et al. Ruthenium complexes of chelating amido-functionalized N-heterocyclic carbene ligands: Synthesis, structure and DFT studies. J Chem Sci 123, 791–798 (2011). https://doi.org/10.1007/s12039-011-0173-5

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