Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

DFT Study of Bis(Crown-Ether) Analogue of Troger’s Base Complexed with Bisammonium Ions: Hydrogen Bonds

  • Published : 2006.11.20
Download PDF
⟨ Previous Next ⟩

Abstract

The optimized structures and complexation energies of bis(18-crown-6-ether) analogue (2) of Trgers base (1) with a series of primary alkylbisammonium ions have been calculated by DFT B3LYP/6-31G(d,p) method. The calculated complexation efficiency (-142.84 kcal/mol) of 2 for butane-1,4-diylbisammonium guest is better than twice of the value (-61.40 kcal/mol) for butylammonium ion. The multiple hydrogen-bond abilities for the complexes are described as the function of the length of the alkyl substituents of the bisammonium guests with normal-alkyl chain [$-(CH_2)_{n-}$, n = 4-8]. The longer bisammonium guest shows the stronger hydrogen-bonding characterizations (the distance and the quasi-linear angle of the N-H…O) to the host 2 than the shorter bisammonium ions. These calculated results agree with the experimental data of the complexation of 2 with bisammonium salts ([$NH_3(CH_2)_nNH_3$] $Cl_2$).

Keywords

References

  1. Molecular Recognition: Chemical and Biochemical Problems, The Proceedings of an International Symposium; Royal Society of Chemistry: Roberts, S. M., Ed.; Dorset Press: Dorset, Great Britain, 1989
  2. Gokel, G. W. In Comprehensive Supramolecular Chemistry; Lehn, J.-M. Ed.; Pergamon Press: Oxford, U. K., 1996; Vol. 1
  3. Calixarenes 2001; Asfari, Z.; Böhmer, V.; Harrowfield, J.; Vicens, J., Eds.; Kluwer: Dordrecht, 2001
  4. Chang, S.-K.; Hwang, H.-S.; Son, H.; Youk, J.; Kang, Y. S. J. Chem. Soc., Chem. Commun. 1991, 217
  5. Chang, S.-K.; Jang, M.; Han, S. Y.; Lee, J. H.; Kang, M. H.; No, K. T. Chem. Lett. 1992, 1937
  6. Han, S. Y.; Kang, M.-H.; Jung, Y. E.; Chang, S.-K. J. Chem. Soc., Perkin Trans. 2 1994, 835
  7. Pappalardo, S.; Parisi, M. F. J. Org. Chem. 1996, 61, 8724 https://doi.org/10.1021/jo9615108
  8. Arnaud-Neu, F.; Fuangswasdi, S.; Notti A.; Pappalardo, S.; Parisi, M. Angew. Chem. Int. Ed. 1998, 37, 112 https://doi.org/10.1002/(SICI)1521-3773(19980202)37:1/2<112::AID-ANIE112>3.0.CO;2-O
  9. Yun, S.; Kim, Y.-O.; Kim, D.; Kim, H. G.; Ihm, H.; Kim, J. K.; Lee, C.-W.; Lee, W. J.; Yoon, J.; Oh, K. S.; Yoon, J.; Park, S.-M.; Kim, K. S. Org. Lett. 2003, 5, 471 https://doi.org/10.1021/ol0273203
  10. 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
  11. Lehninger, A. L. In Biochemistry; Worth Publishers: New York, 1979; p 77 and p 96
  12. Yamamoto, K.; Yumioka, H.; Okamoto, Y.; Chikamatsu, H. Chem. Soc., Chem. Commun. 1987, 168
  13. Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 7017 https://doi.org/10.1021/ja01002a035
  14. Lee, C.- W.; Jung, E. J.; Lee, S. J.; Ahn, K. H.; Kim, K. S. J. Org. Chem. 2000, 65, 7225 https://doi.org/10.1021/jo000766h
  15. Ihm, H.; Yun, S.; Kim, H. G.; Kim, J. K.; Kim, K. S. Org. Lett. 2000, 4, 2897
  16. Izatt, R. M.; Lamb, J. D.; Izatt, N. E.; Rossiter, J. B. E.; Christensen, J. J.; Haymore, B. L. J. Am. Chem. Soc. 1979, 101, 6273 https://doi.org/10.1021/ja00515a019
  17. See for instance the reference 1, pp 511-532
  18. Goodman, M. S.; Jubian, V.; Linton, B.; Hamilton, A. D. J. Am. Chem. Soc. 1995, 117, 11610
  19. Choe, J.-I.; Chang, S.-K.; Ham, S. W.; Nanbu, S.; Aoyagi, M. Bull. Korean Chem. Soc. 2001, 22, 1248
  20. Kim, K.; Lee, H. J.; Choe, J.-I. Bull. Korean Chem. Soc. 2005, 26, 645 https://doi.org/10.5012/bkcs.2005.26.4.645
  21. Hansson, A. P.; Norrby, P.-O.; Waarnmark, K. Tetrahedron Letters 1998, 39, 4565 https://doi.org/10.1016/S0040-4039(98)00807-7
  22. Troger, J. J. Prakt. Chem. 1887, 36, 225 https://doi.org/10.1002/prac.18870360123
  23. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785 https://doi.org/10.1103/PhysRevB.37.785
  24. HyperChem Release 7.5; Hypercube, Inc.: Waterloo, Ontario, 2003
  25. Choe, J.-I.; Kim, K.; Chang, S.-K. Bull. Korean Chem. Soc. 2000, 21, 465 https://doi.org/10.1007/BF02705436
  26. 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.11.3; Gaussian, Inc.: Pittsburgh, PA, 2002
  27. Lee, S. J.; Chung, H. Y.; Kim, K. S. Bull. Korean Chem. Soc. 2004, 25, 1061 https://doi.org/10.5012/bkcs.2004.25.7.1061
  28. Jeffrey, G. A. An Introduction to Hydrogen Bonding; Oxford University Press: Oxford, 1997
  29. Silva, E. D.; Nouar, F.; Nierlich, M.; Rather, B.; Zaworotko, M. J.; Barbey, C.; Navaza, A.; Coleman, A. W. Cryst. Eng. 2003, 6, 123 https://doi.org/10.1016/j.cryseng.2003.11.003
  30. Rather, B.; Moulton, B.; Zaworotko, M. J.; Perret, F.; Morel-Desrosiers, N.; Silva, E. D.; Coleman, A. W. Cryst. Eng. 2003, 6, 15 https://doi.org/10.1016/S1463-0184(03)00047-9

Cited by

  1. Supramolecular Approach to Enantioselective DNA Recognition Using Enantiomerically Resolved Cationic 4-Amino-1,8-naphthalimide-Based Tröger’s Bases vol.79, pp.19, 2014, https://doi.org/10.1021/jo501711g
  2. Design and synthesis of Tröger's base ditopic receptors: host–guest interactions, a combined theoretical and experimental study vol.13, pp.4, 2015, https://doi.org/10.1039/C4OB02266A
  3. One-pot facile synthesis of 4-amino-1,8-naphthalimide derived Tröger's bases via a nucleophilic displacement approach vol.15, pp.35, 2017, https://doi.org/10.1039/C7OB01835E
  4. Microwave-assisted Solvent-free Synthesis of Some Dimethine Cyanine Dyes, Spectral Properties and TD-DFT/PCM Calculations vol.28, pp.12, 2006, https://doi.org/10.5012/bkcs.2007.28.12.2382
  5. Substituent Effect on Diastereoselectivity in Photochemistry of Valerophenone vol.28, pp.7, 2006, https://doi.org/10.5012/bkcs.2007.28.7.1156
  6. 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
  7. Monomethine cyanine dyes with an indole nucleus: Microwave-assisted solvent-free synthesis, spectral properties and theoretical studies vol.82, pp.3, 2006, https://doi.org/10.1016/j.dyepig.2009.03.005