Crown Ether Ditopic Receptors for Ammonium Salts with High Affinity for Amino Acid Ester Salts
DOI:
https://doi.org/10.29356/jmcs.v53i4.973Keywords:
Ditopic Receptors, Binding Constant, Crown Ethers, Alkyl Ammonium, Amino AcidAbstract
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.
Downloads
Download data is not yet available.
References
1. Guy, P. A.; Gremaud, E.; Richoz, J.; Turesky, R. J. J. Chromatogr., A 2000, 883, 89-102.
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.
8. Colera, M.; Costero, A. M.; Gaviña, P.; Gil, S. Tetrahedron: Asymmetry 2005, 16, 2673-2679.
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.
12. Tsubaki, K., Tanaka, H., Furuta, T., Tanaka, K., Kinoshita, T., Fuji, K. Tetrahedron 2002, 58, 5611-5617.
13. Galán, A.; Andreu, D.; Echavarren, A. M.; Prados, P.; De Mendoza, J. J. Am. Chem. Soc. 1992, 114, 1511-1512.
14. Reetz, M. T.; Huff, J.; Rudolph, J.; Töllner, K.; Deege, A.; Goddard, R. J. Am. Chem. Soc. 1994, 116, 11588-11589.
15. Barboiu, M. D.; Hovnanian, N. D.; Luca, C.; Cot, L. Tetrahedron. 1999, 55, 9221-9232.
16. Demirel, N.; Bulut, Y.; Hosgören, H. Tetrahedron: Asymmetry. 2004, 15, 2045-2049.
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.
18. Hansson, A. P.; Norrby, P.-O.; Wärnmark, K. Tetrahedron Lett. 1988, 39, 4565-4568.
19. Kryatova, O. P., Kolchinski, A. G., Rybak-Akimova, E. V. Tetrahedron 2003, 231-239.
20. Izatt, R. M.; Lamb, J. D.; Izatt, N. E.; Rossiter, B. E. Jr., Christensen, J. J., Haymore. B. L. J. Am. Chem. Soc. 1979, 101, 6273-6276.
21. Buschmann, H.-J.; Schollmeyer, E.; Mutihac, L. J. Inclusion Phenom. Macrocyclic Chem. 2001, 40, 199-202.
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.
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.
8. Colera, M.; Costero, A. M.; Gaviña, P.; Gil, S. Tetrahedron: Asymmetry 2005, 16, 2673-2679.
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.
12. Tsubaki, K., Tanaka, H., Furuta, T., Tanaka, K., Kinoshita, T., Fuji, K. Tetrahedron 2002, 58, 5611-5617.
13. Galán, A.; Andreu, D.; Echavarren, A. M.; Prados, P.; De Mendoza, J. J. Am. Chem. Soc. 1992, 114, 1511-1512.
14. Reetz, M. T.; Huff, J.; Rudolph, J.; Töllner, K.; Deege, A.; Goddard, R. J. Am. Chem. Soc. 1994, 116, 11588-11589.
15. Barboiu, M. D.; Hovnanian, N. D.; Luca, C.; Cot, L. Tetrahedron. 1999, 55, 9221-9232.
16. Demirel, N.; Bulut, Y.; Hosgören, H. Tetrahedron: Asymmetry. 2004, 15, 2045-2049.
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.
18. Hansson, A. P.; Norrby, P.-O.; Wärnmark, K. Tetrahedron Lett. 1988, 39, 4565-4568.
19. Kryatova, O. P., Kolchinski, A. G., Rybak-Akimova, E. V. Tetrahedron 2003, 231-239.
20. Izatt, R. M.; Lamb, J. D.; Izatt, N. E.; Rossiter, B. E. Jr., Christensen, J. J., Haymore. B. L. J. Am. Chem. Soc. 1979, 101, 6273-6276.
21. Buschmann, H.-J.; Schollmeyer, E.; Mutihac, L. J. Inclusion Phenom. Macrocyclic Chem. 2001, 40, 199-202.
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.
Downloads
Published
2019-06-19
Issue
Section
Regular Articles
License
Authors who publish with this journal agree to the following terms:
- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
