Structural and Spectroscopic Study of Cyclopentadienylcobalt N-Phenyl-o-benzoquinone Dilmines. A Case for Delocalized π Bonding

Michal E. Gross, James A. Ibers, William C. Trogler*

*Corresponding author for this work

Research output: Contribution to journalArticle

29 Scopus citations


The compounds (η5-C5H5)Co(HNC6X4NC6X5), X = H and F, are produced by photolysis of (η5-C5H5)Co(C6X5N4C6X5). The crystal structure of the complex (η5-C5H5)Co(HNC6F4NC6F5) has been determined at −60 °C by single-crystal X-ray diffraction techniques and shown to contain a bidentate α-diimine moiety, bonded through the nitrogen atoms to (η5-cyclopentadienyl)cobalt. The metallacycle and perfluorophenylene ring are essentially coplanar. Short Co-N and N-C bond lengths in the former are indicative of delocalized π bonding. An intense π → π* transition of the metallacycle dominates the electronic absorption spectrum. The C5 portion of the C5H5 ring is planar; however, the H atoms are bent out of the plane toward the Co atom by an average of 0.07 Å. The C-C distances in the C5H5 ring show a significant distortion from idealized D5h geometry. Crystals of C17H6CoF9N2 are triclinic, space group Ci1—P1̄, with two formula units in a unit cell of dimensions at −60 °C of a = 9.832 (3) Å, b = 9.932 (3) Å, c = 8.922 (3) Å, α = 103.88 (1)°, β = 101.19 (1)°, and λ = 74.02 (1)°. Least-squares refinement of 286 variables has led to a final value of the R index on F2 of 0.054 for 5673 observations; the conventional R index on F is 0.043 for 4054 observations having Fo2 > 3δ(Fo2).

Original languageEnglish (US)
Pages (from-to)530-535
Number of pages6
Issue number3
StatePublished - Jan 1 1982


ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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