Skip to main content
SpringerLink
Log in

Templated assembly of 1,2-bis(chloromercurio) tetrafluorobenzene in the presence of THF

  • Published:
Journal of Chemical Crystallography Aims and scope Submit manuscript

Abstract

Slow evaporation of a THF solution containing the bidentate Lewis acid 1,2-bis(chloromercurio) tetrafluorobenzene (1) , yields colorless crystals of the complex 1⋅μ2-THF (2) as indicated by elemental analysis, thermal gravimetric analysis and 13C CPMAS solid-state NMR spectroscopy. As shown by X-ray analysis, the oxygen atom of the THF molecules bridges the two mercury center of the bidentate Lewis acid. Compound 2 forms an extended structure that features channels filled with THF molecules. In this structure, the individual molecules of the organomercurial are held together by π-π and Hg ⋅⋅⋅ Cl interactions. Immersion of 2 in water results in THF loss to afford 1,2-bis(chloromercurio) tetrafluorobenzene in a pure form. Exposure to THF vapor results in a stoichiometric uptake and formation of a solid whose composition corresponds to that of 2.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Schmidtchen, F.P.; Berger, M. Chem. Rev. 1997, 97, 1609-1646.

    PubMed  Google Scholar 

  2. Kaufmann, D.E.; Otten, A. Angew. Chem., Int. Ed. Engl. 1994, 33, 1832-1834.

    Google Scholar 

  3. Dietrich, B. Pure Appl. Chem. 1993, 65, 1457-1464.

    Google Scholar 

  4. Wuest, J.D. Acc. Chem. Res. 1999, 32, 81-89.

    Google Scholar 

  5. Vaugeois, J.; Simard, M.; Wuest, J.D. Coord. Chem. Rev. 1995, 145, 55-73.

    Google Scholar 

  6. Hawthorne, M.F.; Zheng, Z. Acc. Chem. Res. 1997, 30, 267-276.

    Google Scholar 

  7. Hawthorne, M.F. Pure Appl. Chem. 1994, 66, 245-254.

    Google Scholar 

  8. Piers, W.E.; Irvine, G.J.; Williams, V.C. Eur. J. Inorg. Chem. 2000, 2131-2142.

  9. Lopez, P.; Oh, T. Tetrahedron Lett. 2000, 41, 2313-2317.

    Google Scholar 

  10. Lee, H.; Diaz, M.; Hawthorne, M.F. Tetrahedron Lett. 1999, 40, 7651-7655.

    Google Scholar 

  11. Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307-11308.

    Google Scholar 

  12. Wuest, J.D.; Zacharie, B. J. Am. Chem. Soc. 1985, 107, 6121-6123.

    Google Scholar 

  13. Shriver, D.F.; Biallas, M.J. J. Am. Chem. Soc. 1967, 89, 1078-1081.

    Google Scholar 

  14. Katz, H.E. J. Org. Chem. 1985, 50, 5027-5032.

    Google Scholar 

  15. Horner, J.H.; Squatritto, P.J.; McGuire, N.; Riebenspies, J.P.; Newcomb, M. Organometallics 1991, 10, 1741-1750.

    Google Scholar 

  16. Tschinkl, M.; Schier, A.; Riede, J.; Gabbaï, F.P. Inorg. Chem. 1997, 36, 5706-5711.

    PubMed  Google Scholar 

  17. Altmann, R.; Jurkschat, K.; Schuermann, M.; Dakternieks, D.; Duthie, A. Organometallics 1998, 17, 5858-5866.

    Google Scholar 

  18. Uhl, W.; Hannemann, F. J. Organomet. Chem. 1999, 579, 18-23.

    Google Scholar 

  19. Katz, H.E. J. Org. Chem. 1989, 54, 2179-2183.

    Google Scholar 

  20. Nozaki, K.; Yoshida, M.; Takaya, H. Bull. Chem. Soc. Jpn. 1996, 69, 2043-2052.

    Google Scholar 

  21. Saied, O.; Simard, M.; Wuest, J.D. Organometallics 1998, 17, 1128-1133.

    Google Scholar 

  22. Gabbaï, F.P.; Schier, A.; Riede, J.; Hynes, M.J. Chem. Commun. 1998, 897-898.

  23. Wuest, J.D.; Zacharie, B. Organometallics 1985, 4, 410-411.

    Google Scholar 

  24. Lee, H.; Diaz, M.; Knobler, C.B.; Hawthorne, M.F. Angew. Chem., Int. Ed. Engl. 2000, 39, 776-778.

    Google Scholar 

  25. Lee, H.; Knobler, C.B.; Hawthorne, M.F. Angew. Chem., Int. Ed. Engl. 2001, 40, 2124-2126.

    Google Scholar 

  26. Chistyakov, A.L.; Stankevich, I.V.; Gambaryan, N.P.; Struchkov, Y.T.; Yanovsky, A.I.; Tikhonova, I.A.; Shur, V.B. J. Organomet. Chem. 1997, 536, 413-424.

    Google Scholar 

  27. Shur, V.B.; Tikhonova, I.A.; Yanovskii, A.I.; Struchkov, Y.T.; Petrovskii, P.V.; Panov, S.Y.; Furin, G.G.; Vol'pin, M.E. J. Organomet. Chem. 1991, 418, C29-C32.

    Google Scholar 

  28. Shur, V.B.; Tikhonova, I.A.; Yanovskii, A.I.; Struchkov, Y.T.; Petrovskii, P.V.; Panov, S.Y.; Furin, G.G.; Vol'pin, M.E. Dokl. Akad. Nauk SSSR 1991, 321, 1002-1004.

    Google Scholar 

  29. Shur, V.B.; Tikhonova, I.A.; Dolgushin, F.M.; Yanovsky, A.I.; Struchkov, Y.T.; Volkonsky, A.Y.; Solodova, E.V.; Panov, S.Y.; Petrovskii, P.V.; Vol'pin, M.E. J. Organomet. Chem. 1993, 443, C19-C21.

    Google Scholar 

  30. Wuest, J.D.; Zacharie, B. J. Am. Chem. Soc. 1987, 109, 4714-4715.

    Google Scholar 

  31. Gardinier, J.R.; Gabbaï, F.P. J. Chem. Soc. Dalton Trans. 2000, 2861-2865.

  32. Tschinkl, M.; Schier, A.; Riede, J.; Gabbaï, F.P. Organometallics 1999, 18, 1747-1753.

    Google Scholar 

  33. Beauchamp, A.L.; Olivier, M.J.; Wuest, J.D., Zacharie, B. Organometallics 1987, 6, 153-156.

    Google Scholar 

  34. Simard, M.; Vaugeois, J.; Wuest, J.D. Organometallics 1998, 17, 1215-1219.

    Google Scholar 

  35. Simard, M.; Vaugeois, J.; Wuest, J.D. J. Am. Chem. Soc. 1993, 115, 370-372.

    Google Scholar 

  36. Simard, M.; Vaugeois, J.; Wuest, J.D. J. Am. Chem. Soc. 1998, 120, 13016-13022.

    Google Scholar 

  37. Tschinkl, M.; Schier, A.; Riede, J.; Gabbaï, F.P. Angew. Chem., Int. Ed. Engl. 1999, 38, 3547-3549.

    Google Scholar 

  38. Schmidbaur, H.; öller, H.-J., Wilkinson, D.L.; Huber, B. Chem. Ber. 1989, 122, 31-36.

    Google Scholar 

  39. Tschinkl, M.; Bachman, R.E.; Gabbaï, F.P. Organometallics, 2000, 19, 2633-2636.

    Google Scholar 

  40. Yang, X.; Zheng, Z.; Knobler, C.B.; Hawthorne, M.F. J. Am. Chem. Soc. 1993, 115, 193-195.

    Google Scholar 

  41. Tikhonova, I.A.; Dolgushin, F.M.; Yanovsky, A.I.; Starikova, Z.A.; Petrovskii, P.V.; Furin, G.G.; Shur, V.B. J. Organomet. Chem. 2000, 613, 60-67.

    Google Scholar 

  42. Beckwith, J.D.; Tschinkl, M.; Picot, A.; Tsunoda, M.; Bachman, R; Gabbaï, F.P. Organometallics 2001, 20, 3169-3174.

    Google Scholar 

  43. Pyykkö, P.; Straka, M. Phys. Chem. Chem. Phys. 2000, 2, 2489-2493.

    Google Scholar 

  44. Canty, A.J.; Deacon, G.B. Inorg. Chim. Acta 1980, 45, L225.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Texas A&M University, College Station, Texas, 77843-3255

    Martin Tschinkl & François P. Gabbaï

Authors
  1. Martin Tschinkl
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. François P. Gabbaï
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to François P. Gabbaï.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Tschinkl, M., Gabbaï, F.P. Templated assembly of 1,2-bis(chloromercurio) tetrafluorobenzene in the presence of THF. Journal of Chemical Crystallography 33, 595–598 (2003). https://doi.org/10.1023/A:1024941725790

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1024941725790

Search

Navigation