Crown Ether Ditopic Receptors for Ammonium Salts with High Affinity for Amino Acid Ester Salts
DOI:
https://doi.org/10.29356/jmcs.v53i4.973Palabras clave:
Ditopic Receptors, Binding Constant, Crown Ethers, Alkyl Ammonium, Amino AcidResumen
Two bis crown ether receptors were synthesized and tested as host molecules for protonated forms of alkyl amines and amino acid esters. Molecular recognition studies were conducted in CH2Cl2:MeOH (92:8) by spectrophotometric UV/Vis titrations and
by spectrometric 1H NMR titrations in CDCl3. The calculated binding constants are in the range 102-105 M-1. A high affinity for L-amino acid methyl ester derivatives was found. A theoretical study at the DFT level of the synthesized receptor and some analog ligands with three different ammonium ions helps to rationalize the experimentally found trends.
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2. (a) Ohgaki, H.; Takayama, S.; Sugimura, T. Mutat. Res. 1991, 259, 399-410. (b) Wakabayashi, K.; Nagao, M.; Esumi, H.; Sugimura, T. Cancer Res.1992, 52, 2092S-2098S.
3. (a) Sutherland, I. O. Pure Appl. Chem. 1989, 61, 1547-1554. (b) Voyer, N.; Lamothe, J. Tetrahedron 1995, 51, 9241-9284.
(c) Gokel, G. W.; Abel, E. Comprehensive Supramolecular Chemistry; Vol. 1, Elsevier: Oxford, England, 1996;.(d) Gokel,
G. W.; Leevy, W. M.; Weber, M. E. Chem. Rev. 2004, 104, 2723-2750.
4. (a) Hayashi, T.; Nonogushi, M.; Aya, T.; Ogoshi, H. Tetrahedron Lett.1997, 38, 1603. (b) Ema, T.; Misawa, S.; Nemugaki, S.; Sakai, T.; Utaka, M. Chem. Lett. 1997, 487-488.
5. (a)Tsubacki, K.; Kusumoto, T.; Hayashi, N.; Nuruzzaman, M.; Fuji, K. Org. Lett. 2002, 4, 2313-2316. (b) de Silva, A. P.;
Sandanayake, K. R. A. S. Angew. Chem. Int. Ed. Engl. 1990, 29, 1173-1175.
6. (a) Feuster, E. K.; Glass, T. E. J. Am. Chem. Soc. 2003, 125, 16174-16175.(b) Mohr, G. J. Chem. Eur. J. 2004, 10, 1082-1090.
7. (a) Zimmerman, S. C.; Wendland, M. S.; Rakow, N. A.; Zharov, I.; Suslick, K. S. Nature 2002, 418, 399-402. (b) Mertz, E.; Zimmerman, S. C. J. Am. Chem. Soc. 2003, 125, 3424-3425.
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9. Jung, Y. E., Song, B. M., Chang, S.-K. J. Chem. Soc. Perkin Trans. 2 1995, 2031-2034.
10. Voyer, N.; Deschênes, D.; Bernier, J.; Roby, J. J. Chem. Soc., Chem. Commun. 1992, 134-136.
11. Hernández, J. V.; Oliva, A. I.; Simón, L.; Muñiz, F. M.; Grande, M.; Morán, J. R. Tetrahedron Lett. 2004, 45, 4831-4833.
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17. Breccia, P.; Van Gool, M.; Pérez-Fernández, R.; Martín- Santamaría, S.; Gago, F.; Padros, P.; De Mendoza, J. J. Am. Chem. Soc. 2003, 125, 8270-8284.
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22. (a) Defen, W.; Xiaoqiang, S.; Dengjin, W.; Hongwen, H. Youji Huaxue 1987, 3, 219-223. (b) Xiaochun, Ch.; Defen, W.; Denjing,
W.; Hongwen, H. Chem. Res. Chin. Univ. 1991, 7, 255-260. (c) Dengjin, W.; Defen, W.; Xiaoqiang, S.; Hongwen, H. Gaodeng Xuexiao Huaxue Xuebao 1990, 11(7), 672-675. (d) Defen, W.; Denjing, W.; Hongwen, H. Gaodeng Xuexiao Huaxue Xuebao 1990, 11(3), 276-270.
23. Jaffe, H.H.; Orchin, M. Theory and Applications of Ultraviolet Spectroscopy. John Wiley & Sons, USA, 1962, p. 186.
24. Connors, K. A. Binding Constants. The Measurement of Molecular Complex Stability. John Wiley & Sons, USA, 1987, p. 24.
25. Schneider, H.-J.; Yatsimirsky, A. K.: Principles and Methods in Supramolecular Chemistry. John Wiley & Sons, England, 2000, p.142.
26. Marquis, D.; Desvergne, J.-P.; Bouas-Laurent, H. J. Org. Chem.1995, 60, 7984-7996.
27. Gaviña, F.; Luis, S.V.; Costero, A.M.; Burgete, M.I.; Rebek, J. J. Am. Chem. Soc. 1988, 110, 7140-7143.
28. Al-Jallal, N. A.; Al-Kahtani, A. A.; El-Azhary, A. A. J. Phys. Chem. A, 2005, 109(16), 3694-3703.
29. Buschmann, H. –J.; Mutihac, L.; Jansen, K. J. Inclusion Phenom. Macrocyclic Chem. 2001, 39, 1-11.
30. Zhu, L.-N.; Gao, S.; Huo, L.-H. Acta Cryst. E63 2007, o4924.
31. Lehn, J. M., Supramolecular Chemistry VCH, Germany, 1995, p. 26-28.
32. Ramírez, J. Z.; Vargas, R.; Garza, J. J. Mex. Chem. Soc. 2008, 52, 31-35.
33. Guo, H.; Sirois, S.; Proynov, E. I.; Salahub, D. R. Density Functional Theory and its Applications to Hydrogen-bonded Systems. Theoretical Treatments of Hydrogen bonding; Hadži, D., Ed.; John Wiley & Sons Ltd: Chichister, UK, 1997.
34. Vogel, A. I.; Tatchell, A. R.; Furnis, B. S.; Hannaford, A. J.; Smith, P.W.G. Vogel’s Textbook of Practical Organic Chemistry.5th Edition. Prentice Hall, 1989.
35. Shishkina, S. V.; Shishkin, O. V.; Grygorash R. Y.; Mazepa, A. V.; Rakipov, I. M.; Yakshin, V. V.; Kotlyar, S. A.; Kamalov, G. L. J. Molecular Struct. 2007, 832 199-208
36. Gaussian 03, Revision D.01, M. J. Frisch, G. W. Trucks, H. B.
Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, and J. A. Pople, Gaussian, Inc., Wallingford CT, 2004.
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