Ammonium boranes for the selective complexation of cyanide or fluoride ions in water

Journal of the American Chemical Society

Volumn 129, Issue 39, 2007, Pages 11978-11986

  Hudnall, Todd W ^a   Gabbaï, François P ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM BORANES; CATIONIC BORANES;

AMMONIUM COMPOUNDS; COMPLEXATION; COMPUTATIONAL METHODS; NEGATIVE IONS; WATER;

CYANIDES;

2 DIMESITYLBORYL N,N DIMETHYLANILINE; 4 DIMESITYLBORYL N,N DIMETHYLANILINE; AMMONIUM BORANE DERIVATIVE; AMMONIUM DERIVATIVE; AMPHOLYTE; ANILINE DERIVATIVE; BENZOYL PEROXIDE; BORANE DERIVATIVE; BROMINE; CHLORINE; CYANIDE; FLUORIDE; IODINE; NITRITE; PHOSPHORIC ACID DERIVATIVE; SULFURIC ACID; UNCLASSIFIED DRUG; WATER;

ACIDITY; ANION TRANSPORT; ARTICLE; BINDING AFFINITY; CHEMICAL REACTION KINETICS; COMPLEX FORMATION; HYDRATION; ISOMERISM; REACTION TIME; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

ANIONS; BORANES; CRYSTALLOGRAPHY, X-RAY; CYANIDES; FLUORIDES; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; METHANOL; MODELS, MOLECULAR; QUATERNARY AMMONIUM COMPOUNDS; SOLVENTS; WATER;

EID: 34848826861     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja073793z     Document Type: Article

References (80)

1. Holland, M. A.; Kozlowski, L. M. Clinical pharmacy 1986, 5, 737.
2. Baud, F. J. Hum. Exp. Toxicol. 2007, 26, 191.
3. Aaseth, J.; Shimshi, M.; Gabrilove, J. L.; Birketvedt, G. S. J. Trace Elem. Exp. Med. 2004, 17, 83.
4. Carton, R. J. Fluoride 2006, 39, 163.
5. Worm, K.; Schmidtchen, F. P. Angew. Chem., Int. Ed. 1995, 34, 65.
6. Boiocchi, M.; Del Boca, L.; Gomez, D. E.; Fabbrizzi, L.; Licchelli, M.; Monzani, E. J. Am. Chem. Soc. 2004, 126, 16507.
7. Lin, Z.-H.; Ou, S.-J.; Duan, C.-Y.; Zhang, B.-G.; Bai, Z.-P. Chem. Commun. 2006, 624.
8. Martinez-Manez, R.; Sancenon, F. Chem. Rev. 2003, 103, 4419.
9. Choi, K.; Hamilton, A. D. Coord. Chem. Rev. 2003, 240, 101.
10. Bondy, C. R.; Loeb, S. J. Coord. Chem. Rev. 2003, 240, 77.
11. Gale, P. A. Coord. Chem. Rev. 2003, 240, 191.
12. Sessler, J. L.; Camiolo, S.; Gale, P. A. Coord. Chem. Rev. 2003, 240, 17.
13. Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609.
14. Sun, S.-S.; Lees, A. J. Chem. Commun. 2000, 1687.
15. Anzenbacher, P., Jr.; Tyson, D. S.; Jursikova, K.; Castellano, F. N. J. Am. Chem. Soc. 2002, 124, 6232.
16. Chen, C.-L.; Chen, Y.-H.; Chen, C.-Y.; Sun, S.-S. Org. Lett. 2006, 8, 5053.
17. Ros-Lis, J. V.; Garcia, B.; Jimenez, D.; Martinez-Manez, R.; Sancenon, F.; Soto, J.; Gonzalvo, F.; Valldecabres, M. C. J. Am. Chem. Soc. 2004, 126, 4064.
18. Ros-Lis, J. V.; Martinez-Manez, R.; Soto, J. Chem. Commun. 2002, 2248.
19. Garcia, F.; Garcia, J. M.; Garcia-Acosta, B.; Martinez-Manez, R.; Sancenon, F.; Soto, J. Chem. Commun. 2005, 2790.
20. Yang, Y.-K.; Tae, J. Org. Lett. 2006, 8, 5721.
21. Tomasulo, M.; Sortino, S.; White, A. J. P.; Raymo, F. M. J. Org. Chem. 2006, 71, 744.
22. Tomasulo, M.; Raymo, F. M. Org. Lett. 2005, 7, 4633.
23. Chung, Y.; Lee, H.; Ahn, K. H. J. Org. Chem. 2006, 71, 9470.
24. Ros-Lis, J. V.; Martinez-Manez, R.; Soto, J. Chem. Commun. 2005, 5260.
25. Badugu, R.; Lakowicz, J. R.; Geddes, C. D. Curr. Anal. Chem. 2005, 1, 157.
26. Badugu, R.; Lakowicz, J. R.; Geddes, C. D. Dyes Pigm. 2005, 64, 49.
27. Badugu, R.; Lakowicz, J. R.; Geddes, C. D. Anal. Biochem. 2004, 327, 82.
28. Badugu, R.; Lakowicz, J. R.; Geddes, C. D. Anal. Chim. Acta 2004, 522, 9.
29. Badugu, R.; Lakowicz, J. R.; Geddes, C. D. J. Am. Chem. Soc. 2005, 127, 3635.
30. Palomares, E.; Martinez-Diaz, M. V.; Torres, T.; Coronado, E. Adv. Funct. Mater. 2006, 16, 1166.
31. Liu, H.; Shao, X.-B.; Jia, M.-X.; Jiang, X.-K.; Li, Z.-T.; Chen, G.-J. Tetrahedron 2005, 61, 8095.
32. Kim, Y.-H.; Hong, J.-I. Chem. Commun. 2002, 512.
33. Poland, K.; Topoglidis, E.; Durrant, J. R.; Palomares, E. Inorg. Chem. Commun. 2006, 9, 1239.
34. Chow, C.-F.; Lam, M. H. W.; Wong, W.-Y. Inorg. Chem. 2004, 43, 8387.
35. Bresner, C.; Day, J. K.; Coombs, N. D.; Fallis, I. A.; Aldridge, S.; Coles, S. J.; Hursthouse, M. B. Dalton Trans. 2006, 3660.
36. Bresner, C.; Aldridge, S.; Fallis, I. A.; Jones, C.; Ooi, L.-L. Angew. Chem.. Int. Ed. 2005, 44, 3606.
37. Dusemund, C.; Sandanayake, K. R. A. S.; Shinkai, S. J. Chem. Soc. Chem. Commun. 1995, 333.
38. Yamamoto, H.; Ori, A.; Ueda, K.; Dusemund, C.; Shinkai, S. Chem. Commun. 1996, 407.
39. Cooper, C. R.; Spencer, N.; James, T. D. Chem. Commun. 1998, 1365.
40. Arimori, S.; Davidson, M. G.; Fyles, T. M.; Hibbert, T. G.; James, T. D.; Kociok-Koehn, G. I. Chem. Commun. 2004, 1640.
41. DiCesare, N.; Lakowicz, J. R. Anal. Biochem. 2002, 301, 111.
42. Yamaguchi, S.; Akiyama, S.; Tamao, K. J. Am. Chem. Soc. 2001, 123, 11372.
43. Yamaguchi, S.; Shirasaka, T.; Akiyama, S.; Tamao, K. J. Am. Chem. Soc. 2002, 124, 8816.
44. Kubo, Y.; Yamamoto, M.; Ikeda, M.; Takeuchi, M.; Shinkai, S.; Yamaguchi, S.; Tamao, K. Angew. Chem., Int. Ed. 2003, 42, 2036.
45. Sole, S.; Gabbaï, F. P. Chem. Commun. 2004, 1284.
46. Parab, K.; Venkatasubbaiah, K.; Jäkle, F. J. Am. Chem. Soc. 2006, 128, 12879.
47. Miyata, M.; Chujo, Y. Polym. J. (Tokyo) 2002, 34, 967.
48. Liu, Z.-Q.; Shi, M.; Li, F.-Y.; Fang, Q.; Chen, Z.-H.; Yi, T.; Huang, C.-H. Org. Lett. 2005, 7, 5481.
49. Liu, X. Y.; Bai, D. R.; Wang, S. Angew. Chem., Int. Ed. 2006, 45, 5475.
50. Sun, Y.; Ross, N.; Zhao, S. B.; Huszarik, K.; Jia, W. L.; Wang, R. Y.; Macartney, D.; Wang, S. J. Am. Chem. Soc. 2007, 129, 7510.
51. Agou, T.; Kobayashi, J.; Kawashima, T. Org. Lett. 2005, 7, 4373.
52. Sakuda, E.; Funahashi, A.; Kitamura, N. Inorg. Chem. 2006, 45, 10670.
53. Katz, H. E. J. Org. Chem. 1985, 50, 5027.
54. Melaimi, M.; Gabbaï, F. P. J. Am. Chem. Soc. 2005, 127, 9680.
55. Williams, V. C.; Piers, W. E.; Clegg, W.; Elsegood, M. R. J.; Collins, S.; Marder, T. B. J. Am. Chem. Soc. 1999, 121, 3244.
56. Badr, I. H. A.; Meyerhoff, M. E. J. Am. Chem. Soc. 2005, 127, 5318.
57. Chaniotakis, N.; Jurkschat, K.; Mueller, D.; Perdikaki, K.; Reeske, G. Eur. J. Inorg. Chem. 2004, 2283.
58. Agou, T.; Kobayashi, J.; Kawashima, T. Inorg. Chem. 2006, 45, 9137.
59. Chiu, C.-W.; Gabbaï, F. P. J. Am. Chem. Soc. 2006, 128, 14248.
60. Lee, M. H.; Gabbaï, F. P. Inorg. Chem., published online June 2, 2007, http://dx.doi.org;10.1021/ic700360a.
61. Chiu, C.-W.; Gabbai, F. P. Angew. Chem., Int. Ed. 2007, 46, 1723.
62. Agou, T.; Kobayashi, J.; Kim, Y.; Gabbaï, F. P.; Kawashima, T. Chem. Lett. 2007, in press.
63. Lee, M. H.; Agou, T.; Kobayashi, J.; Kawashima, T.; Gabbaï, F. P. Chem. Commun. 2007, 1133.
64. Bauman, A. Mikrochim. Acta 1977, 1, 69.
65. Albrecht, K.; Kaiser, V.; Boese, R.; Adams, J.; Kaufmann, D. E. Perkin 2000, 2, 2153.
66. Yuan, Z.; Entwistle, C. D.; Collings, J. C.; Albesa-Jove, D.; Batsanov, A. S.; Howard, K. A. J.; Kaiser, H. M.; Kaufmann, D. E.; Poon, S.-K.; Wong, W.-Y.; Jardin, C.; Fathallah, S.; Boucekkine, A.; Halet, J.-F.; Marder, T. B. Chem. Eur. J. 2006, 12, 2758.
67. Yuan, Z.; Taylor, N. J.; Marder, T. B.; Williams, I. D.; Kurtz, S. K.; Cheng, L. T. J. Chem. Soc., Chem. Commun. 1990, 1489.
68. Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett. 1996, 255, 327.
69. Tomasi, J.; Cammi, R.; Mennucci, B. Int. J. Quantum Chem. 1999, 75, 783.
70. Welch, G. C.; Cabrera, L.; Hollink, E.; Stephan, D. W. Abstracts of Papers; 232nd ACS National Meeting, San Francisco, CA, Sept. 10-14, 2006; American Chemical Society: Washington, DC, 2006.
71. Welch, G. C.; Juan, R. R. S.; Masuda, J. D.; Stephan, D. W. Science 2006, 314, 1124.
72. Stahl, R.; Lambert, C.; Kaiser, C.; Wortmann, R.; Jakober, R. Chem. Eur. J. 2006, 12, 2358.
73. Yamaguchi, S.; Shirasaka, T.; Tamao, K. Org. Lett. 2000, 2, 4129.
74. Zhao, C. H.; Wakamiya, A.; Inukai, Y.; Yamaguchi, S. J. Am. Chem. Soc. 2006, 128, 15934.
75. Cavalli, V.; Silva, D. C.; Machado, C.; Machado, V. G.; Soldi, V. J. Fluoresc. 2006, 16, 77.
76. Baraldi, I.; Brancolini, G.; Momicchioli, F.; Ponterini, G.; Vanossi, D. Chem. Phys. Lett. 2003, 288, 309.
77. Roesler, R.; Piers, W. E.; Parvez, M. J. Organomet. Chem. 2003, 680, 218.
78. Lambert, C.; Stadler, S.; Bourhill, G.; Braeuchle, C. Angew. Chem., Int. Ed. 1996, 35, 644.
79. Kuz'mina, L. G.; Struchkov, Y. T.; Lemenovsky, D. A.; Urazowsky, I. F. J. Organomet. Chem. 1984, 277, 147.
80. A full derivation of the equation used to fit the data is provided in the Supporting Information.