Recognition of anions and neutral guests by dicationic pyridine-2,6- dicarboxamide receptors

Journal of Organic Chemistry

Volumn 75, Issue 7, 2010, Pages 2259-2273

  Dorazco González, Alejandro ^a   Höpfl, Herbert ^b   Medrano, Felipe ^b   Yatsimirsky, Anatoly K ^a  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^b CENTRO DE INVESTIGACIONES QUÍMICAS   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

ANION BINDING; ANION COMPLEXATION; ELECTROSTATIC CHARGES; FLUORESCENT SENSING; HIGH AFFINITY; INHIBITORY EFFECT; NMR TITRATION; PYRIDINIUM; PYRIDYL; SIMPLE ROTATION;

AMIDES; CHLORINE COMPOUNDS; ELECTROSTATICS; FLUORESCENCE; HYDROGEN BONDS; ISOMERS; NEGATIVE IONS; NUCLEAR MAGNETIC RESONANCE; PROTONS; PYRIDINE; RIGID STRUCTURES; UREA;

CRYSTAL STRUCTURE;

AMIDE; ANION; HYDROGEN; PROTON; PYRIDINE DERIVATIVE; PYRIDINIUM DERIVATIVE; SODIUM CHLORIDE; UREA;

ARTICLE; CALCULATION; COMPLEX FORMATION; CRYSTAL STRUCTURE; ELECTRICITY; FLUORESCENCE; HYDROGEN BOND; ISOMER; METHODOLOGY; PROTON NUCLEAR MAGNETIC RESONANCE; TITRIMETRY;

EID: 77950336148     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100037m     Document Type: Article

References (73)

1. Reviews: (a) Gale, P. A.; García-Garrido, S. E.; Garric, J. Chem. Soc. Rev. 2008, 37, 51-190.
2. (b) Bates, G. W.; Gale, P. A. Struct. Bonding (Berlin) 2008, 129, 1-44.
3. (c) Sessler, J. L.; Gale, P. A.; Cho, W.-S. Anion Receptor Chemistry; Royal Society of Chemistry: Cambridge, UK, 2006.
4. (d) Steed, J. W. Chem. Commun. 2006, 2637-2649.
5. (e) Amendola, V.; Bonizzoni, M.; EstebanGómez, D.; Fabbrizzi, L.; Licchelli, M.; Sancenón, F.; Taglietti, A. Coord. Chem. Rev. 2006, 250, 1451.
6. (f) Davis, A. P. Coord. Chem. Rev. 2006, 250, 2939.
7. (g) Gale, P. A. Acc. Chem. Res. 2006, 39, 465.
8. (h) Gale, P. A. Cooord. Chem. Rev. 2003, 240, 1.
9. (i) Schmidtchen, F. P. Coord. Chem. Rev. 2006, 250, 2918.
10. (j) Gunnlaugsson, T.; Glynn, M.; Hussey, G. M.; Kruger, P. E.; Pfeffer, F. M. Coord, Chem. Rev. 2006, 250, 3094.
11. (k.) Beer, P. D.; Hayes, E. Coord. Chem. Rev. 2003, 240, 167.
12. (l) Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 486.
13. (m) Kubik, S. Chem. Soc. Rev. 2009, 38, 585-605.
14. Kavallieratos, K.; Bertao,C.M.; Crabtree, R.H.J.Org. Chem. 1999, 64, 1675-1683.
15. (a) Kang, S. O.; Hossain, Md. A.; Bowman-James, K. Coord. Chem. Rev. 2006, 250, 3038-3052.
16. (b) Kang, S. O.; Begum, R. A.; Bowman-James, K. Angew. Chem., Int. Ed. 2006, 45, 7882-7894.
17. (a) Chmielewski, M. J.; Zielinski, T.; Jurczak, J. Pure. Appl. Chem. 2007, 79, 1087-1096.
18. (b) Szumna, A.; Jurczak, J. Eur. J. Org. Chem. 2001, 4031-4039.
19. (a) Evans, L. S.; Gale, P. A.; Light, M. E.; Quesada, R. Chem. Commun. 2006, 965.
20. (b) Brooks, S. J.; Edwards, P. R.; Gale, P. A.; Light, M. E. New J. Chem. 2006, 30, 65.
21. Choi, K.; Hamilton, A. D. Coord. Chem, Rev. 2003, 240, 101-110.
22. (a) Claramunt, R. M.; Herranz. F.; Santa Maria. M. D.; Pinilla, E.; Torres, M. R.; Elguero, J. Tetrahedron 2005, 61, 5089-5100.
23. (b) Fisher, M. G.; Gale, P. A.; Light, M. E. New J. Chem. 2007, 31, 1583.
24. (c) Chang, S. K.; Van Engen, D.; Fan, E.; Hamilton, A. D. J. Am. Chem. Soc 1991, 113, 7640-7645.
25. Deetz, M. J.; Shang, M.; Smith, B. D. J. Am. Chem. Soc. 2000, 122, 6201-6207.
26. Hughes, M. P.; Smith, B. D. J. Org. Chem. 1997, 62, 4492-4499.
27. Santacroce, P. V.; Davis, J. T.; Light, M. E.; Gale, P. A.; Iglesias-Sánchez, J. C.; Prados, P.; Quesada, R. J. Am. Chem. Soc. 2007, 129, 1886-1887.
28. Hossain, M. A.; Kang, S. O.; Llinares, J. M.; Powell, D.; Bowman-James, K. Inorg. Chem. 2003, 42, 5043-5045.
29. Chang, S.-Y.; Kim, H. S.; Chang. K.-J.; Jeong, K.-S. Org. Lett. 2004, 6, 181-184.
30. (a) Pennarun, G.; Granotier, C.; Gauthier, L. R.; Gomez, D.; Hbffschir, F.; Mandine, E.; Riou, J.-F.; Mergny, J.-L.; Mailliet, P.; Boussin, F. D. Oncogene 2005, 24, 2917-2928.
31. (b) Monchaud, D.; Allain, C.; TeuladeTichou, M.-P. Bioorg. Med. Chem. Lett. 2006, 16, 4842-4845.
32. (c) De Cian, A.; Cristofari, G.; .Reichenbach, P.; De Lemos, E.; Monchaud, D.; Teulade-Fichou, M.-P.; Shin-ya, K.; Lacroix, L.; Lingner, J.; Mergny, J.-L. Proc Natl. Acad. Sci. U.S.A. 2007, 104, 17347-17352.
33. Jeong, K.-S.; Cho, Y. L. Tgjrahedron Lett. 1997, 38, 3279-3282.
34. Turner, D. R.; Paterson, M. J.; Steed, J. W. J. Org. Chem. 2006, 71, 1598-1608.
35. (a) Filby, M. H.; Dickson, S. J.; Zaccheroni, N.; Prodi, L.; Bonacchi, S.; Montalti, M.; Paterson, M. J.; Humphries, T. D.; Chiorboli, C.; Steed, J. W. J. Am, Chem. Soc 2008, 130, 4105-4113.
36. (b) Wallace, K. J.; Belcher, W. J.; Turner. D. R.; Syed, K. F.; Steed. J. W. J. Am. Chem. Soc, 2003, 125, 9699-9715.
37. (a) Amendola, V.; Boiocchi, M.; Fabbrizzi, L.; Palchetti, A. Chem. Em: J. 2005, 11, 120-127.
38. (b) Amendola, V.; Boiocchi, M.; Fabbrizzi, L.; Palchetti, A. Chem. Eur. J. 2005, 11, 5648-5660.
39. (a) Wisner, J. A.; Beer, P. D.; Berry, N. G.; Tomapatanaget, B. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4983-4986.
40. (b) Sambrook, M. R.; Beer, P. D.; Wisner, J. A.; Paul, R. L.; Cowley, A. R.; Szemes, F.; Drew, M. G. B. J. Am. Chem. Soc. 2005, 127, 2292.
41. Yoon, J.; Kim, S. K.; Singh, N. J.; Kim, K. S. Chem. Soc. Rev. 2006, 35, 355-360.
42. Dinares, I.; Garcia de Miguel, C.; Mesquida, N.; Alcalde, E. J. Org. Chem. 2009, 74, 428-485.
43. Ghosh. K.; Sarkar, A. R.; Masanta, G. Tetrahedron Lett. 2007, 48, 8725-8729.
44. (a) Hossain, Md. A.; Kang, S. O.; Powell, D.; Bowman-James, K. Inorg. Chem. 2003, 42, 1397-1399.
45. (b) Kang, S. O.; Powell, D.; BowmanJames, K. J. Am. Chem, Soc 2005, 127, 13478-13479.
46. Light, M. E.; Gale, P. A.; Navakhun, K. Acta Crystallogr. 2006, E62, o1097-o1098.
47. Pedzisa, L.; Hay, B. P. J. Org. Chem. 2009, 74, 2554-2560.
48. Steiner, T. Acta Crystahogr. 1998, B54, 456-463.
49. Hay. B. P.; Firman, T. K.; Moyer, B. A. J. Am. Chem. Soc, 2005, 127, 1810-1819.
50. Hyperquad does not have an option for fitting the NMR titrations data, but the fitting can be performed by using the option for absorbance titration data provided the product of the chemical shift by total receptor concentration is used as a variable.
51. Pérez-Casas, C.; Yatsimirsky, A. K. J. Org. Chem. 2008, 73, 2275-2284.
52. Izutsu, K. Acid-Base Dissociation Constants in. Dipolar Aprotic Solvents; Blackwell Scientific Publications: Oxford, UK, 1990.
53. - the profile in Figure 11 was fitted to the scheme involving deprotonation and association equilibria with a known value of K by Hyperquad.
54. Verkman, A. S.; Sellers, M. C.; Chao. A. C.; Leung. T.; Ketcham, R. Anal. Biochem. 1989, 178, 366-1361
55. Amendola, V.; Fabbrizzi, L.; Monzani, E. Chem. - Eur. J. 2004, 10, 76-82.
56. Carter, P. W.; Di Magnot, S. C.; Porter, J. D.; Streitwieser, A. J. Phys. Chem. 1993, 97, 1085-1096.
57. Janz, G. J.; Tomkins, R. P. T. Nonaqueous Electrolytes Handhook; Academic Press: New York, 1972; Vol.1.
58. In, S.; Cho, S. J.; Lee, K. H.; Kang, J. Org. Lett. 2005, 7, 3993-3996.
59. Niu, H.-T.; Yin, Z.; Su, D.; Niu, D.; Ao, Y.; He, J.; Cheng, J.-P. Tetrahedron 2008, 64, 6300-6306.
60. Schneider, H.-J.; Yatsimirsky, A. K. Chem. Soc, Rev. 2008, 37, 263
61. Jain, S. L.; Bhattacharyya, M. H. L.; Slawin, A. M. Z.; Crayston, J. A.; Woollins, J. D. Dalton Trans. 2004, 862-871.
62. (a) Braker Analytical X-ray Systems, SMART: Bruker Molecular Analysis Research. Tool, Versions 5.057 and. 5.618, 1997 and 2000.
63. (b) Bruker Analytical X-ray Systems. SAINT+NT, Versions 6.01 and 6.04, 1999 and 2001.
64. (c) Slieldrick, G. M. SHELX86, Program for Crystal Structure Solution; University of Göttingen: Göttingen, Germany, 1986.
65. (d) Bruker Analytical X-ray Systems, SHELXTL-NT, Versions 5.10 and 6.10, 1999 and 2000
66. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837-838.
67. (a) Jaguar, Version 7.5; Schrödinger LLC: New York, 2008.
68. (b) Jaguar, Version 7.6; Schrödinger LLC: New York, 2009.
69. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
70. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
71. (a) Tannor, D. J.; Marten, B.; Murphy, R.; Friesner, R. A.; Stikoff, D.; Nicholls, A.; Ringnalda, M.; Goddard, W. A., Ill; Honig, B. J. Am. Chem. Soc, 1994, 116, 11-875.
72. (b) Marten, B.; Kim, K.; Cortis, C.; Friesner, R. A.; Murphy, R. B.; Ringnalda, M. N.; Sitkoff, D.; Honig, B. J. Phys. Chem. 1996, 100, 11-775.
73. Gans, P.; Sabatini, A.; Vacca, A. Talganta 1996, 43, 1739-1753.