Skip to main content
Log in

Conformations and Structures of Two Novel Upper Rim Disubstituted Derivatives of Tetra-O-alkylcalix[4]arene: The Effect of Substituents

  • Published:
Journal of inclusion phenomena and macrocyclic chemistry Aims and scope Submit manuscript

Abstract

Two new calix[4]arene derivatives, 5,17-dinitro-26,28-dimethyoxy-25,27-dipropoxycalix[4]arene (4) and 5,17-diamino-26,28-dimethyoxy-25,27-dipropoxycalix[4]arene (5), have been synthesized and fully characterized. The 1H NMR spectra measured in different solvents and temperatures indicated that the dominant conformer is partial cone for 4 and cone for 5, though there are some variations in relative ratio of partial cone to cone conformers. The structures of partial cone 4 and cone 5 are determined by X-ray crystallography. The different conformational behavior in compounds 4 and 5 is governed by the two substituents at the upper rim. The repulsion of the dipole due to the p-nitro substituents and weak interaction between methoxy group and the inverted anisole ring in the 4 may be responsible for stabilizing the partial cone conformation.

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.

Institutional subscriptions

Similar content being viewed by others

References

  1. C.D. Gutsche: In J.F. Stoddart (ed.), Calixarenes Revisited – Monographs in Supramolecular Chemistry, vol. 6, The Royal Society of Chemistry, Cambridge (1998), p. 4.

  2. A. Ikeda S. Shinkai (1997) Chem. Rev. 97 1713 Occurrence Handle11851464

    PubMed  Google Scholar 

  3. A. Pochini R. Ungaro (1996) Calix[4]arene and related hosts J.M. Lehn F. Vögtle (Eds) Comprehensive Supramolecular Chemistry Pergamon Rugby 103

    Google Scholar 

  4. V. Böhmer (1995) Angew. Chem. Int. Ed. Engl. 34 713

    Google Scholar 

  5. G.D. Enright K.A. Udachin I.L. Moudrakovski J.A. Ripmeester (2003) J. Am. Chem. Soc. 125 9896 Occurrence Handle12914432

    PubMed  Google Scholar 

  6. F. Corbellini L.D. Costanzo M. Crego-Calama S. Geremia D.N. Reinhoudt (2003) J. Am. Chem. Soc. 125 9946 Occurrence Handle12914457

    PubMed  Google Scholar 

  7. P.R.A. Webber P.D. Beer G.Z. Chen V. Felix M.G.B. Drew (2003) J. Am. Chem. Soc. 125 5774 Occurrence Handle12733918

    PubMed  Google Scholar 

  8. R. Asfari J. Harrowfield P. Thuéry J. Vicens (2003) Supramol Chem. 15 69

    Google Scholar 

  9. R. Zadmard M. Junker T. Schrader T. Grawe A. Kraft (2003) J. Org. Chem. 68 6511 Occurrence Handle12919011

    PubMed  Google Scholar 

  10. P. Molenveld J.F.J. Engbersen H. Kooilman A.L. Spek D.N. Reinhoudt (1998) J. Am. Chem. Soc. 120 6726

    Google Scholar 

  11. Y.D. Cao Q.Y. Zheng C.F. Chen H.M. Hu Z.T. Huang (2004) Inorg. Chim. Acta 357 316

    Google Scholar 

  12. P.J.A. Kenis O.F.J. Noordman S. Houbrechts G.J. Hummel Particlevan S. Harkema F.C.J.M. Veggel Particlevan K. Clays J.F.J. Engbersen A. Persoons N.F. Hulst Particlevan D.N. Reinhoudt (1998) J. Am. Chem. Soc. 120 7875

    Google Scholar 

  13. L.C. Groenen J.D. Loon Particlevan W. Verboom S. Harkema A. Casnati R. Ungaro A. Pochini F. Ugozzoli D.N. Reinhoudt (1991) J. Am. Chem. Soc. 113 2385

    Google Scholar 

  14. K. Iwamoto K. Arki S. Shinkai (1991) J. Am. Chem. Soc. 56 4955

    Google Scholar 

  15. T. Harada J.M. Rudziński S. Shinkai (1992) J. Chem. Soc., Perkin Trans. 2 2109

    Google Scholar 

  16. A. Soi W. Bauer H. Mauser C. Moll F. Hampel A. Hirsch (1998) J. Chem. Soc., Perkin Trans. 2 1471

    Google Scholar 

  17. S. Shimizu A. Moriyama K. Kito Y. Sasaki (2003) J. Org. Chem. 68 2187 Occurrence Handle12636379

    PubMed  Google Scholar 

  18. K. Iwamoto S. Shinkai (1992) J. Org. Chem. 57 7066

    Google Scholar 

  19. C.D. Gutsche M. Iqbal (1993) Org. Syn. Coll. VIII 75

    Google Scholar 

  20. C.D. Gutsche J.A. Levine P.K. Sujeeth (1985) J. Org. Chem. 50 5802

    Google Scholar 

  21. A. Arduini M. Fabbi M. Mantovani L. Mirone A. Pochini A. Secchi R. Ungaro (1995) J. Org. Chem. 60 1454

    Google Scholar 

  22. P.J.A. Kenis, E.G. Kerver, B.H.M. Snellink-Ruël, G.J. van Hummel, S. Harkema, M.C. Flipse, R.H. Woudenberg, J.F.J. Engbersen, and D.N. Reinhoudt: Eur. J. Org. Chem. 1089 (1998).

  23. F. Arndt (1955) Org Syn Coll. II 165

    Google Scholar 

  24. Bruker (2000) SMART, SAINT, SADABS and SHELXTL Bruker AXS Inc. Madison, Wisconsin, USA

    Google Scholar 

  25. E. Kelderman L. Derhaeg G.J.T. Heasink W. Verboom J.F.J. Engbersen N.F. Hulst Particlevan A. Persoons D.N. Reinhoudt (1992) Angew. Chem. Int. Ed. Engl. 31 1075

    Google Scholar 

  26. O. Struck L.A.J. Chrisstoffels R.J.W. Lugtenberg W. Verboom G.J. Hummel Particlevan S. Harkema D.N. Reinhoudt (1997) J. Org. Chem. 62 2487 Occurrence Handle11671587

    PubMed  Google Scholar 

  27. C.D. Gutsche B. Dhawan J.A. Levine K.H. No L.J. Bauer (1983) Tetrahedron 39 409

    Google Scholar 

  28. R.K. Juneja K.D. Robinson C.P. Johnson J.L. Atwood (1993) J. Am. Chem. Soc. 115 3818

    Google Scholar 

  29. S. Chowdhury P.E. Georghiou (2001) J. Org. Chem. 66 6257 Occurrence Handle11559171

    PubMed  Google Scholar 

  30. E.B. Brouwer G.D. Enright C.I. Ratcliffe G.A. Facey J.A. Ripmeester (1999) J. Phys. Chem..B 103 10604

    Google Scholar 

  31. E. Nomura A. Hosoda H. Taniguchi (2001) J. Org. Chem. 66 8030 Occurrence Handle11722201

    PubMed  Google Scholar 

  32. F.C. Krebs M. Larsen M. Jørgensen P.R. Jensen M. Bielecki K. Schaumburg (1998) J. Org. Chem. 63 9872

    Google Scholar 

  33. S. Shinkal, K. Iwamoto, K. Araki, and T. Matsuda: Chem. Lett. 1263 (1990).

  34. G.D. Zhou L.Y. Duan (1995) The Foundations of Structure Chemistry EditionNumber2 Peking University Publishing House Beijing China 265

    Google Scholar 

  35. R.F.W. Bader (1990) Atoms in Molecules A quantum Theory. Clarendon Press Oxford

    Google Scholar 

  36. R.F.W. Bader (1998) J. Phys. Chem. A 102 7314

    Google Scholar 

  37. M.J. Frisch G.W. Trucks H.B. Schlegel G.E. Scuseria M.A. Robb J.R. Cheeseman V.G. Zakrzewski J.A. Montgomery SuffixJr. R.E. Stratmann J.C. Burant S. Dapprich J.M. Millam A.D. Daniels K.N. Kudin M.C. Strain O. Farkas J. Tomasi V. Barone M. Cossi R. Cammi B. Mennucci C. Pomelli C. Adamo S. Clifford J. Ochterski G.A. Petersson P.Y. Ayala Q. Cui K. Morokuma D.K. Malick A.D. Rabuck K. Raghavachari J.B. Foresman J. Cioslowski J.V. Ortiz A.G. Baboul B.B. Stefanov G. Liu A. Liashenko P. Piskorz I. Komaromi R. Gomperts R.L. Martin D.J. Fox T. Keith M.A. Al-Laham C.Y. Peng A. Nanayakkara C. Gonzalez M. Challacombe P.M.W. Gill B. Johnson W. Chen M.W. Wong J.L. Andres C. Gonzalez M. Head-Gordon E.S. Replogle J.A. Pople (1998) Gaussian 98 Revision A.11.2, Inc. Pittsburgh PA

    Google Scholar 

  38. Available from Prof. Bader’s Laboratory, McMaster University, Hamilton, Ont. L8S 4M1, Canada.

  39. W. Verboom A. Durie R.J.M. Egberink Z. Asfari D.N. Reinhoudt (1992) J. Org. Chem. 57 1313

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Longgen Zhu.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Yang, G., Jin, C., Li, Y. et al. Conformations and Structures of Two Novel Upper Rim Disubstituted Derivatives of Tetra-O-alkylcalix[4]arene: The Effect of Substituents. J Incl Phenom Macrocycl Chem 52, 119–127 (2005). https://doi.org/10.1007/s10847-004-6331-3

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10847-004-6331-3

Keywords

Navigation