Studies on the bonding of polynuclear heteroaromatic nitrogen ligands to (pentamethylcyclopentadienyl)rhodium dication: the role of nitrogen versus /pi/-complexation on the regioselective hydrogenation of the nitrogen ring
Journal Article
·
· Organometallics; (United States)
The reactions of quinoline (1), isoquinoline (2), 1,2,3,4-tetrahydroquinoline (3), and 2-methylquinoline (4) with (pentamethylcyclopentadienyl)rhodium dication (Cp*Rh(acetone)/sub 3//sup 2+/, Cp*Rh(acetonitrile)/sub 3//sup 2+/, or Cr*Rh(p-xylene)/sup 2+/X/sub 2/; X = PF/sub 6/ or BF/sub 4/) were studied to ascertain nitrogen (N) versus /pi/-bonding. Ligands 1 and 2 were found to form N-bonded rhodium complexes, while ligand 3 preferred /pi/-coordination (/eta//sup 6/). Ligand 4 was found to provide both /pi/- and N-bonded complexes. A single-crystal X-ray structural analysis of a derivative of Cp*Rh(quinoline)(acetonitrile)/sub 2//sup 2+/, (Cp*Rh(quinoline)(/mu/-hydroxo))/sub 2//sup 2+/ synthetic precursors were excellent catalysts or catalyst precursors for the selective hydrogenation of 1, 2, and 4 to their corresponding tetrahydro derivatives. This latter result defines the important role of N-bonding for regioselective nitrogen ring reduction.
- Research Organization:
- Lawrence Berkeley Lab., CA (USA)
- DOE Contract Number:
- AC03-76SF00098
- OSTI ID:
- 6048282
- Journal Information:
- Organometallics; (United States), Journal Name: Organometallics; (United States) Vol. 7:10; ISSN ORGND
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
AROMATICS
AZAARENES
AZINES
BINDING ENERGY
CATALYSIS
CATALYSTS
CATALYTIC EFFECTS
CATIONS
CHARGED PARTICLES
CHEMICAL BONDS
CHEMICAL REACTIONS
COMPLEXES
DATA
ELECTRONIC STRUCTURE
ELEMENTS
ENERGY
EXPERIMENTAL DATA
HETEROCYCLIC COMPOUNDS
HYDROGENATION
INFORMATION
IONS
LIGANDS
NITROGEN
NONMETALS
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PYRIDINES
QUINOLINES
RHODIUM COMPLEXES
TRANSITION ELEMENT COMPLEXES
400201* -- Chemical & Physicochemical Properties
AROMATICS
AZAARENES
AZINES
BINDING ENERGY
CATALYSIS
CATALYSTS
CATALYTIC EFFECTS
CATIONS
CHARGED PARTICLES
CHEMICAL BONDS
CHEMICAL REACTIONS
COMPLEXES
DATA
ELECTRONIC STRUCTURE
ELEMENTS
ENERGY
EXPERIMENTAL DATA
HETEROCYCLIC COMPOUNDS
HYDROGENATION
INFORMATION
IONS
LIGANDS
NITROGEN
NONMETALS
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PYRIDINES
QUINOLINES
RHODIUM COMPLEXES
TRANSITION ELEMENT COMPLEXES