Open Bis(triazolium) structural motifs as a benchmark to study combined hydrogen- and halogen-bonding interactions in oxoanion recognition processes

Journal of Organic Chemistry

Volumn 79, Issue 15, 2014, Pages 6959-6969

  Zapata, Fabiola ^a   Caballero, Antonio ^a   Molina, Pedro ^a   Alkorta, Ibon ^b   Elguero, José ^b  

^a UNIVERSITY OF MURCIA   (Spain)

^b INSTITUTO DE QUÍMICA MÉDICA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING ENERGY; COMPLEXATION; FLUORESCENCE; HALOGEN COMPOUNDS; NEGATIVE IONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PYRENE;

ASSOCIATION CONSTANT; COMPUTATIONAL STUDIES; EMISSION SPECTROPHOTOMETRY; FLUORESCENT CHEMOSENSORS; FLUORESCENT SENSING; HYDROGEN BOND DONORS; NON-COVALENT INTERACTION; RECOGNITION PROCESS;

HYDROGEN BONDS;

ANION; HALOGEN; HYDROGEN; PYRENE; PYRENE DERIVATIVE; PYROPHOSPHATE; TRIAZOLE DERIVATIVE; DIPHOSPHORIC ACID; PYROPHOSPHORIC ACID DERIVATIVE;

ABSORPTION SPECTROPHOTOMETRY; ARTICLE; ATOM; BINDING AFFINITY; CHEMICAL BOND; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; FLAME PHOTOMETRY; FLUORESCENCE; HYDROGEN BOND; MOLECULAR RECOGNITION; MOLECULAR SENSOR; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; RECEPTOR AFFINITY; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ANIONS; DIPHOSPHATES; HALOGENS; HYDROGEN; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; PYRENES; TRIAZOLES;

EID: 84905373526     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo501061z     Document Type: Article

References (89)

1. Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 486-512
2. ONeil, E. J.; Smith, B. D. Coord. Chem. Rev. 2006, 250, 3068-3080
3. Sessler, J. L.; Gale, P. A.; Cho, W.-S. Anion Receptor Chemistry; RSC: Cambridge, 2006.
4. Llinares, J. M.; Powell, D.; Bowman-James, K. Coord. Chem. Rev. 2003, 240, 57-75
5. Martínez-Máñez, R.; Sancenón, F. Coord. Chem. Rev. 2006, 250, 3081-3093
6. Gunnlaugsson, T.; Glynn, M.; Tocci, G. M.; Kruger, P. E.; Pfeffer, F. M. Coord. Chem. Rev. 2006, 250, 3094-3117
7. Rice, C. R. Coord. Chem. Rev. 2006, 250, 3190
8. Gale, P. A.; García-Garrido, S. E.; Garric, J. Chem. Soc. Rev. 2008, 37, 151-190
9. Pérez, J.; Riera, L. Chem. Soc. Rev. 2008, 37, 2658-2667
10. Steed, J. W. Chem. Soc. Rev. 2009, 38, 506-519
11. Kubik, S. Chem. Soc. Rev. 2009, 38, 585-605
12. Hua, Y.; Flood, A. H. Chem. Soc. Rev. 2010, 39, 1262-1271
13. Quiñonero, D.; Garau, C.; Rotger, C.; Frontera, A.; Ballester, P.; Costa, A.; Deyá, P. M. Angew. Chem., Int. Ed. 2002, 41, 3389-3392
14. Alkorta, I.; Elguero, J. J. Am. Chem. Soc. 2002, 124, 8593-8598
15. Mascal, M. Angew. Chem., Int. Ed. 2006, 45, 2890-2893
16. Mascal, M.; Yakovlev, I.; Nikitin, E. B.; Fettinger, J. C. Angew. Chem., Int. Ed. 2007, 46, 8782-8784
17. Hay, B. P.; Bryanttsev, V. S. Chem. Commun. 2008, 2417-2428
18. Schottel, B. L.; Chifotides, H. T.; Dunbar, K. R. Chem. Soc. Rev. 2008, 37, 68-83
19. Barryman, O. B.; Johnson, D. W. Chem. Commun. 2009, 3143-3153
20. Ni, X.-L.; Zeng, N.; Redshaw, C.; Yamato, T. J. Org. Chem. 2011, 76, 5696-5702
21. Metrangolo, P.; Neukirch, H.; Pilati, T.; Resnati, G. Acc. Chem. Res. 2005, 38, 386-395
22. Politzar, P.; Lane, P.; Concha, M. C.; Ma, Y.; Murray, J. S. J. Mol. Modell. 2007, 23, 305-311
23. Metrangolo, P.; Meyer, F.; Pilati, T.; Resnati, G.; Terraneo, G. Angew. Chem., Int. Ed. 2008, 47, 6114-6127
24. Erdélyi, M. Chem. Soc. Rev. 2012, 41, 3547-3557
25. Beale, T. M.; Chudzinski, M. G.; Sarwar, M. G.; Taylor, M. S. Chem. Soc. Rev. 2013, 42, 1667-1680
26. Metrangolo, P.; Resnati, G. Science 2008, 321, 918-919
27. Caronna, T.; Liantonio, R.; Logothetis, T. A.; Metrangolo, P.; Pilati, T.; Resnati, G. J. Am. Chem. Soc. 2004, 126, 4500-4501
28. Sun, A.; Goroff, N. S.; Lauther, J. W. Science 2006, 312, 1030-1034
29. Rissanen, K. CrystEngComm 2008, 10, 1107-1113
30. Carvallo, G.; Metrangolo, P.; Pilati, T.; Resnati, G.; Sansotera, M.; Terraneo, G. Chem. Soc. Rev. 2010, 39, 3772-3783
31. Metrangolo, P.; Carcenac, Y.; Lahtinen, M.; Pilati, T.; Rissanen, K.; Vij, A.; Resnati, G. Science 2009, 323, 1461-1464
32. Fourmigué, M.; Batail, P. Chem. Rev. 2004, 104, 5379-5418
33. Nguyen, H. L.; Horton, P. N.; Hursthouse, M. B.; Legon, A. C.; Bruce, D. W. J. Am. Chem. Soc. 2004, 126, 16-17
34. Metrangolo, P.; Prasang, C.; Resnati, G.; Liantonio, R.; Whitwood, A. C.; Bruce Chem. Commun. 2006, 3290-3292
35. Cincic, D.; Friscic, T.; Jones, W. Chem.-Eur. J. 2008, 14, 747-753
36. Metrangolo, P.; Meyer, F.; Pilati, T.; Proserpio, D. M.; Resnati, G. Cryst. Growth Des. 2008, 8, 654-659
37. Xu, J. W.; Liu, X. M.; Ng, J. K. P.; Lin, T. T.; He, C. B. J. Mater. Chem. 2006, 16, 3540-3595
38. Bruce, D. W.; Metrangolo, P.; Meyer, F.; Prasang, C.; Resnati, G.; Terraneo, G.; A. C. Whitwood, A. C. New J. Chem. 2008, 32, 477-482
39. Zordan, F.; Brammer, L.; Sherwood, P. J. Am. Chem. Soc. 2005, 127, 5979-5989
40. Liantonio, L.; Metrangolo, P.; Meyer, F.; Pilati, T.; Navarrini, W.; Resnati, G. Chem. Commun. 2006, 1819-1821
41. Graeme, R. H.; Paul, J.; John, M.; Llew, R.; Aaron, S. M. Chem.-Eur. J. 2009, 15, 4156-4164
42. Prasang, C.; Nguyen, H. L.; Horton, P. N.; Whitwood, A. C.; Bruce, D. W. Chem. Commun. 2008, 6164-6166
43. Dimitrijevic, E.; Kvak, O.; Taylor, M. S. Chem. Commun. 2010, 46, 9025-9027
44. Sarwar, M. G.; Dragisic, B.; Dimitrijevic, E.; Taylor, M. S. Chem.-Eur. J. 2013, 19, 2050-2058
45. Mele, A.; Metrangolo, P.; Neukirch, H.; Pilati, T.; Resnati, G. J. Am. Chem. Soc. 2005, 127, 14972-14973
46. Sarwar, M. G.; Dragisic, B.; Sagoo, S.; Taylor, M. S. Angew. Chem., Int. Ed. 2010, 49, 1674-1677
47. Chudzinski, M. G.; McClary, C. A.; Taylor, M. S. J. Am. Chem. Soc. 2011, 133, 10559
48. Caballero, A.; White, N. G.; Beer, P. D. Angew. Chem., Int. Ed. 2011, 50, 1845-1848
49. Khilah, N. L.; Wise, M. D.; Beer, P. D. Cryst. Growth. Des. 2011, 11, 4565-4571
50. Walter, S. M.; Kneip, F.; Rout, L.; Schmidtchen, F. P.; Herdtweck, E.; Huber, S. M. J. Am. Chem. Soc. 2012, 134, 8507-8512
51. Zapata, F.; Caballero, A.; White, N. G.; Claridge, T. D. W.; Costa, P. J.; Felix, V.; Beer, P. D. J. Am. Chem. Soc. 2012, 134, 11533-11541
52. Khilah, N. L.; Wise, M. D.; Serpell, C. J.; Thompson, A. L.; White, N. G.; Christensen, K. E.; Beer, P. D. J. Am. Chem. Soc. 2010, 132, 11893-11895
53. Cametti, M.; Raatikainen, K.; Metrangolo, P.; Pilati, T.; Terraneo, G.; Resnati, G. Org. Biomol. Chem. 2012, 10, 1329-1333
54. Gilday, L. C.; White, N. G.; Beer, P. D. Dalton Trans. 2013, 42, 15766-15773
55. Mitsunobu, O. Synthesis 1981, 1, 1-28
56. Hein, J. E.; Tripp, J. C.; Krasnova, L. B.; Sharpless, K. B.; Fokin, V. V. Angew. Chem., Int. Ed. 2009, 48, 8018-8021
57. Park, S. Y.; Yoon, J. H.; Hong, C. S.; Souane, R.; Kim, J. S.; Matthews, S. E.; Vicens, J. J. Org. Chem. 2008, 73, 8212-8218
58. Winnick, F. M. Chem. Rev. 1993, 93, 587-614
59. Basu, G.; Kubasik, M.; Anglos, D.; Secor, B.; Kuki, A. J. Am. Chem. Soc. 1990, 112, 9410-9411
60. Solovyov, K. N.; Borisevich, E. A. Phys.-Usp. 2005, 48, 231
61. Rae, M.; Perez-Balderas, F.; Baleizao, C.; Fedorov, A.; Cavaleiro, J. A. S.; Tomé, A. C.; Berberan-Santos, M. N. J. Phys. Chem. B 2006, 110, 12809-12814
62. HG = variation of molar absorptivity.
63. Lipscombe, W. N.; Sträter, N. Chem. Rev. 1996, 96, 2375-2433
64. Tabary, T.; Lu, J. J. Immunol. Methods 1992, 156, 55
65. Nyren, P. Anal. Biochem. 1987, 167, 235-238
66. Xu, S.; He, M.; Yu, H.; Cai, X.; Tan, X.; Lu, B.; Shu, B. Anal. Biochem. 2001, 299, 188-193
67. Doherty, M.; Becher, C.; Regan, M.; Jones, A.; Ledingham, J. Ann. Rheum. Dis. 1996, 55, 432-436
68. Timms, A. E.; Zhang, Y.; Russell, R. G.; Brown, M. A. Rheumatology 2002, 41, 725-729
69. Sánchez, G.; Curiel, D.; Tatkiewcz, W.; Ratera, I.; Tarraga, A.; Veciana, J.; Molina, P. Chem. Sci. 2014, 5, 2328-2335
70. Caballero, A.; Zapata, F.; González, L.; Molina, P.; Alkorta, I.; Elguero, J. Chem. Commun. 2014, 50, 4680-4682
71. Hynes, M. J. J. Chem. Soc., Dalton Trans. 1993, 311-312
72. ADF2013, SCM, Theoretical Chemistry, Vrije Universiteit, Amsterdam, The Netherlands, http://www.scm.com.
73. Pye, C. C.; Ziegler, T. Theor. Chem. Acc. 1999, 101, 396-408
74. Klamt, A.; Schüürmann, G. J. Chem. Soc., Perkin Trans. 2 1993, 799-805
75. Klamt, A. J. Phys. Chem. 1995, 55, 2224-2235
76. Klamt, A.; Jones, V. J. Chem. Phys. 1996, 105, 9972-9981
77. Gonzalez, C.; Lim, E. C. J. Phys. Chem. A 2003, 107, 10105-10110
78. Grimme, S. J. Comput. Chem. 2004, 25, 1463-1473
79. Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1996, 77, 3865-3868
80. Grimme, S. J. Comput. Chem. 2006, 27, 1787-1799
81. van Lenthe, E.; Baerends, E. J. J. Comput. Chem. 2003, 24, 1142-1156
82. The Nature of the Hydrogen Bond: Outline of a Comprehensive Hydrogen Bond Theory; Gilli, G.; Gilli, P., Eds.; Oxford University Press: New York, 2009.
83. Gilli, P.; Pretto, L.; Bertolasi, V.; Gilli, G. Acc. Chem. Res. 2009, 42, 33-44
84. Halogen Bonding: Fundamentals and Applications; Metrangolo, P.; Resnati, G., Eds.; Springer: Berlin, 2008.
85. Sarwar, M. G.; Dragisic, B.; Salsberg, L. J.; Gouliaras, C.; Taylor, M. S. J. Am. Chem. Soc. 2010, 132, 1646-1653
86. Supramolecular Chemistry of Anions; Bianchi, A.; Bowman-James, K.; García-España, E., Eds.; Wiley-VCH: New York, 1997; p 227.
87. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 3 rd ed. Updated and Enlarged; Wiley-VCH: Weinheim, Germany, 2003; p 140.
88. Schneider, H. J.; Mohammad-Ali, A. K. Receptors for Organic Guest Molecules: General Principles. In Comprehensive Supramolecular Chemistry; Atwood, J. L.; Davies, J. E. D.; MacNicol, D. D.; Vögtle, F., Eds.; Pergamon: Oxford, 1996; Vol. 2, p 75.
89. Smithrud, D. B.; Sanford, E. M.; Chao, I.; Ferguson, S. B.; Carcanague, D. R.; Evanseck, J. D.; Houk, K. N.; Diederich, F. Pure Appl. Chem. 1990, 62, 2227-2236 Raras Raras