Polyfunctional recognition of pyridinedicarboxylate anions with macrocyclic polyamine receptors containing heteroaromatic groups

Journal of Organic Chemistry

Volumn 73, Issue 21, 2008, Pages 8286-8295

  Bazzicalupi, Carla ^a   Bencini, Andrea ^a   Bianchi, Antonio ^a   Borri, Claudia ^a   Danesi, Andrea ^a   Garcia España, Enrique ^b   Giorgi, Claudia ^a   Valtancoli, Barbara ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

^b UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDS; CRYSTAL STRUCTURE; FLOW INTERACTIONS; HYDROGEN; HYDROGEN BONDS; IONS; NEGATIVE IONS; NUCLEAR MAGNETIC RESONANCE; OPTICAL DEVICES; TITRATION; VOLUMETRIC ANALYSIS;

AROMATIC MOIETIES; BIPYRIDINE; HETEROAROMATIC GROUPS; MACROCYCLIC POLYAMINE; MACROCYCLIC RECEPTORS; PHENANTHROLINE; POTENTIOMETRIC TITRATIONS; PYRIDINEDICARBOXYLIC ACIDS; RECOGNITION ABILITIES; SALT BRIDGES; SOLID COMPOUNDS; SPECTROSCOPIC METHODS; STABILITY CONSTANTS; STABLE COMPLEXES; STACKING INTERACTIONS;

SUBSTRATES;

ALIPHATIC CARBOXYLIC ACID; AROMATIC COMPOUND; AZAMETHONIUM; BIPYRIDINE; CARBOXYLIC ACID DERIVATIVE; DICARBOXYLIC ACID DERIVATIVE; MACROCYCLIC COMPOUND; PHENANTHROLINE; POLYAMINE; PYRIDINE DERIVATIVE;

ARTICLE; CALCULATION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CRYSTAL STRUCTURE; ELECTRICITY; EQUILIBRIUM CONSTANT; HYDROGEN BOND; MOLECULAR MODEL; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POTENTIOMETRY; PROTON TRANSPORT; SOLID STATE; TITRIMETRY; ULTRAVIOLET SPECTROSCOPY;

ANIONS; BINDING SITES; CARBOXYLIC ACIDS; HYDROCARBONS, AROMATIC; HYDROGEN BONDING; MACROCYCLIC COMPOUNDS; MODELS, MOLECULAR; POLYAMINES; POTENTIOMETRY; PYRIDINES; SPECTRUM ANALYSIS; STATIC ELECTRICITY;

EID: 55249086268     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801366w     Document Type: Article

References (74)

1. (a) Sessler, J. L.; Gale, P. A.; Cho, W. S. Anion Receptor Chemistry (Monographs in Supramolecular Chemistry); Stoddart, J. F., Ed.; RSC: Cambridge, UK, 2006.
2. (b) Supramolecular Chemistry of Anions; Bianchi, A., Bowman-James, K., Garcia-Espana, E., Ed.; Wiley-VCH: New York, 1997.
3. Kubik, S.; Reyheller, C.; Stüwe, S. J. Incl. Phenom. Macrocycl. Chem. 2005, 52, 137-187.
4. Encyclopedia of Supramolecular Chemistry; Atwood, J. L., Steed, J. W., Ed.; Marcel Dekker: New York, 2004.
5. Special Issue on Anion Coordination Chemistry. Coord. Chem. Rev. 2003, 240, 1-226.
6. Gale, P. A. Coord. Chem. Rev. 2001, 213, 79-128.
7. Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 487-516.
8. Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609-1646.
9. (a) Guillemin, G. J.; Meininger, V.; Brew, B. J. Neurodegenerative Dis. 2005, 2, 166-176.
10. (b) El-Defrawy, S. R.; Boegman, R. J.; Jhamandas, K.; Beninger, R. J. Can. J. Physiol. Pharmacol. 1986, 64, 369-375.
11. (c) Heyes, M. P.; et al. Brain 1992, 115, 1249-1273.
12. (d) Stone, T. W.; Perkins, M. N. Eur. J. Pharmacol. 1981, 72, 411-412.
13. (e) Schwarcz, R.; Whetsell, W. O., Jr.; Mangano, R. M. Science 1983, 219, 316-318.
14. (f) Stone, T. W. Pharmacol. Rev. 1993, 45, 309-379.
15. (a) Anderson, E.; Zink, W.; Xiong, H.; Gendelman, H. E. J. Acquir. Immun. Def. Synd. 2002, 31 (Suppl. 2), S43-54.
16. (b) Heyes, M. P.; Brew, B. J.; Martin, A.; Price, R. W.; Salazar, A. M.; Sidtis, J. J.; Yergey, J. A.; Mouradian, M. M.; Sadler, A. E.; Keilp, J.; Rubinow, D.; Markey, S. P. Ann. Neurol. 1991, 29, 202-209.
17. Shima, M. Bull. Sericult. Exp. Stat. 1955, 14, 427-449.
18. Claydon, N.; Grove, J. J. Invertebr. Pathol. 1982, 40, 413-418.
19. (a) Oyama, J. Rep. Ferment. Res. Inst. 1961, 20, 95-103.
20. (b) Oyama, J.; Nakamura, N.; Tanabe, O. Rep. Ferment. Res. Inst. 1961, 19, 5-81.
21. Asaffz, A.; Cerda-Garcia-Rojas, C.; De la Torre, M. Appl. Microbiol. Biotechnol. 2005, 68, 542-547.
22. (a) Vullev, V. I.; Jones, G. Proceedings of the 222nd ACS National Meeting, American Chemical Society: Washington, DC, 2000; INOR-557.
23. (b) Scott, I. R.; Ellar, D. J. J. Bacteriol. 1978, 135, 133-137.
24. (c) Goodacre, R.; Shann, B.; Gilbert, R. J.; Timmins, E. M.; McGovem, A. C.; Alsberg, B. K.; Kel, l D. B.; Logan, N. A. Anal. Chem. 2000, 72, 119-127.
25. (d) Paulus, H. Anal. Biochem. 1981, 114, 407-410.
26. (e) Fell, N. F.; Pellegrino, P. M.; Gillespie, J. B. Anal. Chim. Acta 2001, 426, 43-50.
27. (f) Pellegrino, P. M.; Fell, N. F.; Rosen, D. L.; Gillespie, J. B. Anal. Chem. 1999, 70, 1755-1760.
28. (g) Beverly, M. B.; Voorthees, K. J.; Hadfield, T. L.; Cody, R. B. Anal. Chem. 2000, 72, 2428-2432.
29. (h) Hindle, A. A.; Hall, E. A. H. Analyst 1999, 124, 1599-1604.
30. (i) Snyder, A. P.; Thornton, S. N; Dworzanski, J. P.; Meuzelaar, H. L. C. Field Anal. Chem. Technol. 1996, 1, 49-59.
31. Zhou, Y.; Yu, B.; Levon, K. Biosens. Bioelectron. 2005, 20, 1851-1855.
32. Hunter, C. A.; Lawson, K. R.; Perkins, J.; Urch, C. J. J. Chem. Soc., Perkin Trans. 2 2001, 651-669.
33. (a) Dougherty, D. A. Science 1996, 271, 163-168.
34. (b) Ma, J. C.; Dougherty, D. A. Chem. Rev. 1997, 97, 1303-1324.
35. Aghabozorg, H.; Saei, A. A.; Ramezanipour, F. Acta Crystallogr. Sect. E: Struct. Rep. Online 2005, 61, o3242.
36. (a) Moghimi, A.; Sharif, M. A.; Aghabozorg, H. Acta Crystallogr. Sect. E: Struct. Rep. Online 2004, 60, o1790.
37. (b) Braga, D.; Bazzi, C.; Maini, L.; Grepioni, F. CrystEngComm 1999, 1, 15.
38. (c) Aghabozorg, H.; Soleimannejad, J.; Sharif, M.; Sheshmani, S.; Moghimi, A. Anal. Sci.: X-Ray Struct. Anal. Online 2005, 21, x73.
39. (d) Ma, C.-L.; Zhang, J.-H. Chin. J. Appl. Chem. 2003, 20, 296.
40. (e) Thanigaimani, K.; T. Muthiah, P.; Lynch, D. E. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 2007, 63, o295.
41. (f) Moghimi, A.; Sheshmani, S.; Shokrollahi, A.; Shamsipur, M.; Kickelbick, G.; Aghabozorg, H. Z. Anorg. Allg. Chem. 2005, 631, 160.
42. (g) Aakeroy, C. B.; Hughes, D. P.; McCabe, J. M.; Nieuwenhuyzen, M. Supramol. Chem. 1998, 9, 127.
43. (h) Aakeroy, C. B.; Hughes, D. P.; McCabe, J. M.; Nieuwenhuyzen, M. Supramol. Chem. 1998, 9, 127.
44. (i) Aghabozorg, H.; Ghadermazi, M.; Sadr-Khanlou, E. Anal. Sci.: X-Ray Struct. Anal. Online 2006, 22, x253.
45. (j) Moghimi, A.; Lippolis, V.; Aghabozorg, H.; Shokrollahi, A.; Shamsipur, M.; Sheshmani, S.; Blake, A. J. Pol. J. Chem. 2006, 80, 1385.
46. (k) Aghabozorg, H.; Ghadermazi, M.; Sheshmani, S. Anal. Sci.: X-Ray Struct. Anal. Online 2006, 22, x231.
47. (l) Fu, A.-Y.; Wang, D.-Q.; Zhang, C.-L. Acta Crystallogr. Sect. E: Struct. Rep. Online 2005, 67, o3119.
48. (m) Sheshmani, S.; Ghadermazi, M.; Aghabozorg, H. Acta Crystallogr. Sect. E: Struct. Rep. Online 2006, 62, o3620.
49. (n) Ng, S. W.; Turnbull, M. M. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 1998, 54, 1025.
50. Peral, F.; Gallego, E. Spectrochim. Acta Part A 2000, 56, 2149-2155.
51. (a) Yamada, S.; Morita, C. J. Am. Chem. Soc. 2002, 124, 8184-8185.
52. (b) Yamada, S.; Morita, C.; Yamamoto, J. Tetrahedron Lett. 2004, 45, 7475-7478.
53. (c) Yamada, S.; Morimoto, Y.; Misono, T. Tetrahedron Lett. 2005, 46, 5673-5676.
54. Acharya, P.; Plashkevych, O.; Morita, C.; Yamada, S.; Chattopadhyaya, J. J. Org. Chem. 2003, 68, 1529-1538.
55. (a) Bianchi, A.; Garcia-España, E. J. Chem. Educ. 1999, 76, 1727-1732.
56. (b) Bencini, A.; Bianchi, A.; Burguete, M. I.; Dapporto, P.; Domenech, A.; Garcia-España, E.; Luis, S. V.; Paoli, P.; Ramirez, J. A. J. Chem. Soc., Perkin Trans. 2 1994, 569-577.
57. Bencini, A.; Bianchi, A.; Giorgi, C.; Fusi, V.; Masotti, A.; Paoletti, P. J. Org. Chem. 2000, 65, 7686-7689.
58. Bazzicalupi, C.; Bencini, A.; Fusi, V.; Giorgi, C.; Paoletti, P.; Valtancoli, B. Inorg. Chem. 1998, 37, 941-948.
59. Micheloni, M.; Paoletti, P.; Bianchi, A. Inorg. Chem. 1985, 24, 3702-3704.
60. Multiscan Procedure; CrysAlis Pro v 1.171.29.2 Oxford Diffraction LTD, Abington, Oxfordshire, England, 2006.
61. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Gagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 1999, 32, 115.
62. Sheldrick, G. M. SHELXL-97; Göttingen, Germany, 1997.
63. Bianchi, A.; Bologni, L.; Dapporto, P.; Micheloni, M.; Paoletti, P. Inorg. Chem. 1984, 23, 1201-1205.
64. (a) Gran, G. Analyst (London) 1952, 77, 661-671.
65. (b) Rossotti, F. J.; Rossotti, H. J. Chem. Educ. 1965, 42, 375-378.
66. Gans, P.; Sabatini, A.; Vacca, A. Talanta 1996, 43, 1739-1753.
67. Marquardt, D. W. J. Soc. Ind. Appl. Math. 1963, 11, 431-441.
68. Freund, J. E. Mathematical Statistics; Prentice Hall: New York, 1962.
69. SPECFIT/32, Global Analysis System, v.3.0, Spectrum Associates, Marlborough, MA, USA, http://www.bio-logic.info/rapid-kinetics/software.html.
70. Covington, A. K.; Paabo, M.; Robinson, R. A.; Bates, R. G. Anal. Chem. 1968, 40, 700-706.
71. (a) Brooks, B. R.; Bruccoleri, R. E.; Olafson, B. D.; States, D. J.; Swaminathan, S.; Karplus, M. J. Comput. Chem. 1983, 4, 187-217.
72. (b) Smith, J. C.; Karplus, M. J. Am. Chem. Soc. 1992, 114, 805-812.
73. Hyperchem β1 Release 7.51 (2002) for Windows Molecular Modelling System, Hypercube, Inc., Gainsville, FL, 32601.
74. Stewart, J. P. P. J. Comput.-Aided Mol. Des. 1990, 4, 1-105.