Skip to main content
Log in

Mercury complexes of an N-heterocyclic carbene derived from a calixarene/azolium cyclophane hybrid

  • Original Article
  • Published:
Journal of Inclusion Phenomena and Macrocyclic Chemistry Aims and scope Submit manuscript

Abstract

Reaction of mercuric acetate with an imidazolium-linked cyclophane incorporating 2,6-phenolic moieties results in formation of an interesting new N-heterocyclic carbene (NHC) complex of mercury. The new complex is cationic and binuclear, incorporating two mercury centres and two bis(NHC) ligands, each mercury atom being bound by two NHC moieties and two phenol/phenoxy moieties. Forms of the complex having coordinating (\( {\text{HgBr}}_{4}^{2 - } \)) and non-coordinating (\( {\text{PF}}_{6}^{ - } \)) counterions have been structurally characterised.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Scheme 2
Fig. 1
Scheme 3
Fig. 2

Similar content being viewed by others

References

  1. Yuan, D., Huynh, H.V.: Syntheses and characterizations of thiolato-functionalized N-heterocyclic carbene Pd(II) complexes with normal and mesoionic binding modes. Dalton Trans. 40, 11698–11703 (2011)

    Article  CAS  Google Scholar 

  2. Bernhammer, J.C., Huynh, H.V.: Nickel(II) benzimidazolin-2-ylidene complexes with thioether- functionalized side chains as catalysts for Suzuki–Miyaura cross-coupling. Organometallics 33, 5845–5851 (2014)

    Article  CAS  Google Scholar 

  3. Bernhammer, J.C., Huynh, H.V.: Benzimidazolin-2-ylidene complexes of palladium(II) featuring a thioether moiety: synthesis, characterization, molecular dynamics, and catalytic activities. Organometallics 33, 1266–1275 (2014)

    Article  CAS  Google Scholar 

  4. Jiménez, M.V., Fernández-Tornos, J., Pérez-Torrente, J.J., Modrego, F.J., Winterle, S., Cunchillos, C., Lahoz, F.J., Oro, L.A.: Iridium(I) complexes with hemilabile N-heterocyclic carbenes: efficient and versatile transfer hydrogenation catalysts. Organometallics 30, 5493–5508 (2011)

    Article  Google Scholar 

  5. Guo, L., Song, X.-Z., Lin, C.-X., Li, Q.-S., Liu, C., Wang, W.-H., Xu, F.-B.: Synthesis of multi-imidazolium salt ligands containing calixarene fragments and their N-heterocyclic carbene Ag(I) macrocyclic complexes. Polyhedron 85, 732–739 (2015)

    Article  CAS  Google Scholar 

  6. Arnold, P.L., Scarisbrick, A.C.: Di- and trivalent ruthenium complexes of chelating, anionic N-heterocyclic carbenes. Organometallics 23, 2519–2521 (2004)

    Article  CAS  Google Scholar 

  7. Arnold, P. L., Rodden, M., Davis, K. M., Scarisbrick, A. C., Blake, A. J., Wilson, C.: Asymmetric lithium(I) and copper(II) alkoxy-N-heterocyclic carbene complexes; crystallographic characterisation and Lewis acid catalysis. Chem. Commun. 1612-1613 (2004)

  8. Deng, H.-N., Xing, Y.-L., Xia, C.-L., Sun, H.-M., Shen, Q., Zhang, Y.: Ionic iron(III) complexes of bis(phenol)-functionalized imidazolium cations: synthesis, structures and catalysis for aryl Grignard cross-coupling of alkyl halides. Dalton Trans. 41, 11597–11607 (2012)

    Article  CAS  Google Scholar 

  9. Zhang, M., Ni, X., Shen, Z.: Synthesis of bimetallic bis(phenolate) N-heterocyclic carbene lanthanide complexes and their applications in the ring-opening polymerization of l-lactide. Organometallics 33, 6861–6867 (2014)

    Article  CAS  Google Scholar 

  10. Waltman, A.A., Grubbs, R.H.: A new class of chelating N-heterocyclic carbene ligands and their complexes with palladium. Organometallics 23, 3105–3107 (2004)

    Article  CAS  Google Scholar 

  11. Aihara, H., Matsuo, T., Kawaguchi, H.: Titanium N-heterocyclic carbene complexes incorporating an imidazolium-linked bis(phenol). Chem. Commun. 2204-2205 (2003)

  12. Li, W.-F., Sun, H.-M., Wang, Z.-G., Chen, M.-Z., Shen, Q., Zhang, Y.: Synthesis and structural characterization of aryloxo-functionalized N-heterocyclic carbene complexes of nickel(II). J. Organomet. Chem. 690, 6227–6232 (2005)

    Article  CAS  Google Scholar 

  13. Mas-Marzá, E., Poyatos, M., Sanaú, M., Peris, E.: A new rhodium(III) complex with a tripodal bis(imidazolylidene) ligand. Synthesis and catalytic properties. Organometallics 23, 323–325 (2004)

    Google Scholar 

  14. Baker, M.V., Brown, D.H., Haque, R.A., Simpson, P.V., Skelton, B.W., White, A.H., Williams, C.C.: Mercury complexes of N-heterocyclic carbenes derived from imidazolium-linked cyclophanes: synthesis, structure, and reactivity. Organometallics 28, 3793–3803 (2009)

    Article  CAS  Google Scholar 

  15. Hesler, V.J., Skelton, B.W., White, A.H., Brown, D.H., Baker, M.V.: Calixarene/azolium cyclophane hybrids: synthesis, structure and conformations. J. Incl. Phenom. Macrocycl. Chem. (2015). doi:10.1007/s10847-015-0491-1

    Google Scholar 

  16. Baker, M.V., Bosnich, M.J., Brown, D.H., Byrne, L.T., Hesler, V.J., Skelton, B.W., White, A.H., Williams, C.C.: Azolium-linked cylophanes: a comprehensive examination of conformations by 1H NMR spectroscopy and structural studies. J. Org. Chem. 69, 7640–7652 (2004)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We thank the Australian Research Council for financial support (DP0344334 to M.V.B., A.H.W.) and an Australian Postgraduate Award (to V.J.H.). We acknowledge the Centre of Microscopy, Characterisation and Analysis, The University of Western Australia (a facility funded by The University of Western Australia, the Australian Government and the State Government of Western Australia) for providing access to facilities, and for scientific and technical assistance.

Conflict of interest

The authors declare that they have no conflict of interest.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Murray V. Baker.

Additional information

Dedicated to Jack Harrowfield and Jacques Vicens: ‘Nil illegitimae abradum!’

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Hesler, V.J., Skelton, B.W., White, A.H. et al. Mercury complexes of an N-heterocyclic carbene derived from a calixarene/azolium cyclophane hybrid. J Incl Phenom Macrocycl Chem 82, 71–78 (2015). https://doi.org/10.1007/s10847-015-0522-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10847-015-0522-y

Keywords

Navigation