DOI QR코드

DOI QR Code

DFT Study of p-tert-Butylcalix[5]crown-6-ether Complexed with Alkylammonium Ions

  • Published : 2007.04.20

Abstract

The structures and energies of p-tert-butylcalix[5]crown-6-ether (1) and its alkylammonium complexes have been calculated by DFT B3LYP/6-31G(d,p) method. We have studied the binding sites of these host-guest complexes focusing on the p-tert-butylcalix[5]arene pocket (endo) or the crown-6-ether moiety (exo) of 1. The smaller alkylammonium cations have the better complexation efficiency with p-tert-butylcalix[5]crown-6- ether than the bulkier alkylammonium ions. For the sec- and tert-butylammonium ions, the hydrogen-bond distances of the exo-complexes are shorter, therefore, stronger than the endo-cases. This DFT calculated result is in parallel with the trend of the experimental association constants of the branched butylammonium ions.

Keywords

References

  1. Molecular Recognition: Chemical and Biochemical Problems; Roberts, S. M., Ed.; The Proceedings of an International Symposium, Royal Society of Chemistry: Dorset Press: Dorset, Great Britain, 1989
  2. Gutsche, C. D. Calixarenes Revisited; The Royal Society of Chemistry, Cambridge, 1998
  3. Calixarenes 2001; Asfari, Z.; Böhmer, V.; Harrowfield, J.; Vicens, J., Eds.; Kluwer: Dordrecht, 2001
  4. Behr, J.-P.; Lehn, J.-M.; Vierling, P. Helv. Chim. Acta 1982, 65, 1853
  5. Fages, F.; Desvergne, J.-P.; Kampke, K.; Bouas-Laurent, H.; Lehn, J.-M.; Meyer, M.; Albrecht-Gary, A.-M. J. Am. Chem. Soc. 1993, 115, 3658
  6. Oh, K. S.; Lee, C.-W.; Choi, H. S.; Lee, S. J.; Kim, K. S. Org. Lett. 2000, 2, 2679
  7. Buhlmann, P.; Pretsch, E.; Bakker, E. Chem. Rev. 1998, 98, 1593 https://doi.org/10.1021/cr970113+
  8. Chang, S.-K.; Hwang, H.-S.; Son, H.; Youk, J.; Kang, Y. S. J. Chem. Soc., Chem. Commun. 1991, 217
  9. Chang, S.-K.; Jang, M.; Han, S. Y.; Lee, J. H.; Kang, M. H.; No, K. T. Chem. Lett. 1992, 1937
  10. Song, B. M.; Chang, S.-K. Bull. Korean Chem. Soc. 1993, 14, 540
  11. Han, S. Y.; Kang, M.-H.; Jung, Y. E.; Chang, S.- K. J. Chem. Soc., Perkin Trans. 2 1994, 835
  12. Jung, Y. E.; Song, B. M.; Chang, S.-K. J. Chem. Soc., Perkin Trans. 2 1995, 2031
  13. Arnaud-Neu, F.; Arnecke, R.; Bohmer, V.; Fanni, S.; Gordon, J. L. M.; Schwing-Weill, M.-J.; Vogt, W. J. Chem. Soc. Perkin Trans. 2 1996, 1855
  14. Gordon, J. L. M.; Bohmer, V.; Vogt, W. Tetrahedron Lett. 1995, 36, 2445 https://doi.org/10.1016/0040-4039(95)00277-J
  15. Pappalardo, S.; Parisi, M. F. Tetrahedron Lett. 1996, 37, 1493 https://doi.org/10.1016/0040-4039(96)00047-0
  16. Arnecke, R.; Bohmer, V.; Cacciapaglia, R.; Dalla Cort, A.; Mandolini, L. Tetrahedron 1997, 53, 4901 https://doi.org/10.1016/S0040-4020(97)00185-3
  17. Bohmer, V.; Dalla Cort, A.; Mandolini, L. J. Org. Chem. 2001, 66, 1900 https://doi.org/10.1021/jo001288d
  18. Casnati, A.; Iacopozzi, P.; Pochini, A.; Ugozzoli, F.; Cacciapaglia, R.; Mandolini, L.; Ungaro, R. Tetrahedron 1995, 51, 591 https://doi.org/10.1016/0040-4020(94)00918-K
  19. Pappalardo, S.; Parisi, M. F. J. Org. Chem. 1996, 61, 8724 https://doi.org/10.1021/jo9615108
  20. Arnaud-Neu, F.; Fuangswasdi, S.; Notti, A.; Pappalardo, S.; Parisi, M. Angew. Chem. Int. Ed. 1998, 37, 112
  21. Giannetto, M.; Mori, G.; Notti, A.; Pappalardo, S.; Paris, M. F. Anal. Chem. 1998, 70, 4631 https://doi.org/10.1021/ac9803840
  22. Salvo, G. D.; Gattuso, G.; Notti, A.; Parisi, M.; Pappalardo, S. J. Org. Chem. 2002, 67, 684 https://doi.org/10.1021/jo015982k
  23. Computational Approaches in Supramolecular Chemistry; Wipff, G., Ed.; Kluwar Academic Publshers: Dordrecht, The Netherlands, 1994
  24. Choe, J.-I.; Kim, K.; Chang, S.-K. Bull. Korean Chem. Soc. 2000, 21, 200
  25. Lee, J. Y.; Lee, S. J.; Choi, H. S.; Cho, S. J.; Kim, K. S.; Ha, T. K. Chem. Phys. Lett. 1995, 232, 67 https://doi.org/10.1016/0009-2614(94)01330-X
  26. Kim, K. S.; Lee, J. Y.; Lee, S. J.; Ha, T. K.; Kim, D. H. J. Am. Chem. Soc. 1994, 116, 7399 https://doi.org/10.1021/ja00095a050
  27. Choi, H. S.; Cho, S. J.; Kim, K. S. Proc. Natl. Acad. Sci. 1998, 95, 12094 https://doi.org/10.1073/pnas.95.21.12094
  28. Kim, K. S.; Cui, C.; Cho, S. J. J. Phys. Chem. 1998, 102, 461 https://doi.org/10.1021/jp972385m
  29. Cho, S. J.; Hwang, H.; Park, J.; Oh, K. S.; Kim, K. S. J. Am. Chem. Soc. 1996, 118, 485 https://doi.org/10.1021/ja953242l
  30. Choe, J.-I.; Chang, S.-K.; Ham, S. W.; Nanbu, S.; Aoyagi, M. Bull. Korean Chem. Soc. 2001, 22, 1248
  31. Choe, J.-I.; Lee, S. H.; Oh, D.-S.; Chang, S.-K.; Nanbu, S. Bull. Korean Chem. Soc. 2004, 25, 190 https://doi.org/10.5012/bkcs.2004.25.2.190
  32. HyperChem Release 7.5; Hypercube, Inc.: Waterloo, Ontario, Canada, 2003
  33. Choe, J.-I.; Kim, K.; Chang, S.-K. Bull. Korean Chem. Soc. 2000, 21, 465
  34. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A. Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.9; Gaussian, Inc.: Pittsburgh, PA, 1998
  35. Choe, H. S.; Kim, D.; Tarakeshwar, P.; Suh, S. B.; Kim, K. S. J. Org. Chem. 2002, 67, 1848 https://doi.org/10.1021/jo016335w
  36. Chem3D Molecular Modeling and Analysis, Version 7.0; Cambridge Soft Corporation: Cambridge, 2002

Cited by

  1. H-NMR and DFT analysis of the phthalimide–hydrazone probes as selective anion sensor vol.29, pp.6, 2017, https://doi.org/10.1080/10610278.2016.1264074
  2. Microwave-assisted Solvent-free Synthesis of Some Dimethine Cyanine Dyes, Spectral Properties and TD-DFT/PCM Calculations vol.28, pp.12, 2007, https://doi.org/10.5012/bkcs.2007.28.12.2382
  3. Physical Chemistry Research Articles Published in the Bulletin of the Korean Chemical Society: 2003-2007 vol.29, pp.2, 2008, https://doi.org/10.5012/bkcs.2008.29.2.450
  4. DFT Study of p-tert-Butylcalix[6]aryl Ester Complexed with Alkylammonium Ions vol.30, pp.3, 2009, https://doi.org/10.5012/bkcs.2009.30.3.589
  5. DFT Study of p-tert-Butylcalix[6]aryl Ester Complexed with Alkylammonium Ions vol.30, pp.3, 2009, https://doi.org/10.5012/bkcs.2009.30.3.589
  6. Monomethine cyanine dyes with an indole nucleus: Microwave-assisted solvent-free synthesis, spectral properties and theoretical studies vol.82, pp.3, 2007, https://doi.org/10.1016/j.dyepig.2009.03.005
  7. Theoretical Insight into the Mechanism of an Efficient ʟ-Proline-catalyzed Transamidation of Acetamide with Benzylamine vol.35, pp.9, 2007, https://doi.org/10.5012/bkcs.2014.35.9.2673