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Synthesis and Characterization of a Bis(imino)-N-heterocyclic Carbene Analogue to Bis(imino)pyridine Iron Complexes

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    Synthesis and Characterization of a Bis(imino)-N-heterocyclic Carbene Analogue to Bis(imino)pyridine Iron Complexes
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    Eugene F. Merkert Chemistry Center, Department of Chemistry, Boston College, 2609 Beacon Street, Chestnut Hill, Massachusetts, 02467
    *Tel: 617-552-6725. E-mail: [email protected]
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    Organometallics

    Cite this: Organometallics 2012, 31, 21, 7343–7350
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    https://doi.org/10.1021/om300885d
    Published October 22, 2012
    Copyright © 2012 American Chemical Society
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    Abstract

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    New bis(imino)-N-heterocyclic carbene ligands have been synthesized, and the corresponding iron complexes have been isolated and characterized. Whereas imidazole-derived complexes exhibited exclusively bidentate binding modes, 4,5,6-trihydropyrimidylidene-based ligands adopted a tridentate pincer conformation analogous to complexes of 2,6-bis(imino)pyridines. Bonding in the five-coordinate bis(imino)-N-heterocyclic carbene complex displayed considerably contracted iron–ligand bond distances in comparison to those in the analogous bis(imino)pyridine iron complex. Of particular note was an extraordinarily short iron–carbene carbon bond distance (1.812(2) Å). In addition to demonstrating differences in bonding, the isoelectronic structures have different electrochemical properties that reflect the ability of the carbene to stabilize both oxidized and reduced forms of the parent organometallic species.

    Copyright © 2012 American Chemical Society

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    Figures, tables, and CIF files giving 1H NMR spectra of 4, 9, and 10 and crystallographic data for 4, 9, 10, and 13 (CCDC reference numbers 900880–900883), including tables of crystal data and structure refinement, bond lengths, angles, atomic coordinates, equivalent isotropic displacement parameters, and anisotropic displacement parameters. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cited By

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    This article is cited by 30 publications.

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    Organometallics

    Cite this: Organometallics 2012, 31, 21, 7343–7350
    Click to copy citationCitation copied!
    https://doi.org/10.1021/om300885d
    Published October 22, 2012
    Copyright © 2012 American Chemical Society
    Request reuse permissions

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