Structural criteria for the rational design of selective ligands: Convergent hydrogen bonding sites for the nitrate anion

Journal of the American Chemical Society

Volumn 126, Issue 25, 2004, Pages 7925-7934

  Hay, Benjamin P ^a   Gutowski, Maciej ^a   Dixon, David A ^b   Garza, Jorge ^c   Vargas, Rubicelia ^c   Moye, Bruce A ^d  

^a PACIFIC NORTHWEST NATIONAL LABORATORY   (United States)

^b UNIVERSITY OF ALABAMA   (United States)

^c DEPARTAMENTO DE QUÍMICA   (Mexico)

^d OAK RIDGE NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN BONDS; METHANE; REACTION KINETICS;

LIGANDS; STABLE GEOMETRIES;

CRYSTAL STRUCTURE;

AMIDE; ANION; LIGAND; METHANE; METHANOL; N METHYLFORMAMIDE; NITRATE; WATER;

ARTICLE; CHEMICAL INTERACTION; COMPLEX FORMATION; CRYSTAL STRUCTURE; ELECTRONICS; GEOMETRY; HYDROGEN BOND; STRUCTURE ANALYSIS;

EID: 3042601541     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0487980     Document Type: Article

References (121)

1. (a) Supramolecular Chemistry of Anions; Bianchi, A., Bowman-James, K., García-España, E., Eds.; Wiley-VHC: New York, 1997.
2. (b) Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609-1646.
3. (c) Gale, P. A. Coord. Chem. Rev. 2000, 199, 181-233.
4. (d) Gale, P. A. Coord. Chem. Rev. 2001, 213, 79-128.
5. (d) Beer P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 486-516.
6. (e) Fitzmaurice, R. J.; Kyne, G. M.; Douheret, D.; Kilburn, J. D. J. Chem. Soc., Perkin Trans. 1 2002, 841-864.
7. (f) McKee, V.; Nelson, J.; Town, R. M. Chem. Soc. Rev. 2003, 32, 309-325.
8. (g) Martinez-Manez, R.: Sacenon, F. Chem. Rev. 2003, 103, 4419-4476.
9. (h) Suksai, C.; Tuntulani, T. Chem. Soc. Rev. 2003, 32, 192-202.
10. (i) Choi, K.; Hamilton, A. D. Coord. Chem. Rev. 2003, 240, 101-110.
11. (j) Lambert, T. N.; Smith, B. D. Coord. Chem. Rev. 2003, 240, 129-141.
12. (k) Davis, A. P.; Joos, J.-B. Coord. Chem. Rev. 2003, 240, 143-156.
13. (l) Beer, P. D.; Hayes, E. J. Coord. Chem. Rev. 2003, 240, 167-189.
14. (m) Gale, P. A. Coord. Chem. Rev. 2003, 240, 191-221.
15. Schneider, H.-J.; Yatsimirsky, A. K. Principles and Methods in Supramolecular Chemistry; John Wiley and Sons: Chichester, 2000.
16. Moyer, B. A.; Bonnesen, P. V. Supramolecular Chemistry of Anions; Bianchi, A., Bowman-James, K., García-España, E., Eds.; Wiley-VHC: New York, 1997; Chapter 1, pp 1-44.
17. (a) Choi, K.; Hamilton, A. D. J. Am. Chem. Soc. 2003, 125, 10 241-10 249.
18. (b) Kang, S. O.; Llinares, J. M.; Powell, D.; VanderVelde, D.; Bowman-James, K. J. Am. Chem. Soc. 2003,]25, 10 152-10 153.
19. (c) Hossain, M. A.; Kang, S. O.; Powell, D. Bowman-James, K. Inorg. Chem. 2003, 42, 1397-1399.
20. (d) Otto, S.; Kubik, S. J. Am. Chem. Soc. 2003, 125, 7804-7805.
21. (e) Sun, S.-S.; Lees, A. J.; Zavalij, P. Y. Inorg. Chem. 2003, 42, 3445-3453.
22. (f) Zhang, X.; Guo, L.; Wu, F.-Y.; Jiang, Y.-B. Org. Lett. 2003, 5, 2667-2670.
23. (g) Camiolo, S.; Gale, P. A.; Hursthouse, M. B.; Light, M. E.; Warriner, C. N. Tetrahedron Lett. 2003, 44, 1367-1369.
24. (h) Camiolo, S.; Gale, P. A.; Hursthouse, M. B.; Light, M. E. Org. Biomol. Chem. 2003, 1, 741-744.
25. (i) Bondy, C. R.; Loeb, S. J. Coord. Chem. Rev. 2003, 240, 77-99.
26. (a) Hossain, M. A.; Kang, S. O.; Llinares, J. M.; Powell, D.; Bowman-James, K. Inorg. Chem. 2003, 42, 5043-5045.
27. (b) Inoue, Y.; Kanbara, T.; Yamamoto, T. Tetrahedron Lett. 2003, 44, 5167-5169.
28. Hettche, F.; Hoffman, R. W. New. J. Chem. 2003, 27, 172-177.
29. (a) Tobey, S. L.; Anslyn, E. V. J. Am. Chem. Soc. 2003, 125, 10963-10970.
30. (b) Morehouse, P.; Hossain, M. A.; Llinares, J. M.; Powell, D.; Bowman-James, K. Inorg. Chem. 2003, 42, 8131-8133.
31. (c) Llinares, J. M.; Powell, D.; Bowman-James, K. Coord. Chem. Rev. 2003, 240, 55-57.
32. (d) Farrell, D.; Gloe, K.; Gloe, K.; Goretzki, G.; McKee, V.; Nelson, J.; Nieuwenhuyzen, M.; Pal, I.; Stephan, H.; Town, R. M.; Wichmann, K. Dalton Trans. 2003, 1961-1968.
33. (a) Sessler, J. L.; Dan Pantos, G.; Katayev, E.; Lynch, V. M. Org. Lett. 2003, 5, 4141-4144.
34. (b) Levitskaia, T. G.; Marquez, M.; Sessler, J. L.; Shriver, J. A.; Vercouter, T.; Moyer, B. A. Chem. Commun. 2003, 2248-2249.
35. (c) Bucher, C.; Zimmerman, R. S.; Lynch, V.; Sessler, J. L. Chem. Commun. 2003, 1646-1647.
36. (d) Sessler, J. L.; An, D.; Cho, W.-S.; Lynch, V. J. Am. Chem. Soc. 2003, 125, 13 646-13 647.
37. (e) Lee, C.-H.; Na, H.-K.; Yoon, D.-W.; Won, D.-H.; Cho, W.-S.; Lynch, V. M.; Shevchuk, S. V.; Sessler, J. L. J. Am. Chem. Soc. 2003, 125, 7301-7306.
38. (f) Warriner, C. N.; Gale, P. A.; Light, M. E.; Hursthouse, M. B. Chem. Commun. 2003, 1810-1811.
39. (g) Vega, I. E. D.; Camiolo, P. A.; Hursthouse, M. B.; Light, M. E. Chem. Commun. 2003, 1686-1687.
40. (h) Sessler, J. L.; Camiolo, S.; Gale, P. A. Coord. Chem. Rev. 2003, 240, 17-55.
41. Yun, S.; Ihm, H.; Kim, H. G.; Lee, C.-W.; Indrajit, B.; Oh, K. S.; Gong, Y. J.; Lee, J. W.; Yoon, J.; Lee, H. C.; Kim, K. S. J. Org. Chem. 2003, 68, 2467-2470.
42. (a) Sisson, A. L.; Clare, J. P.; Taylor, L. H.; Charmant, J. P. H.; Davis, A. P. Chem. Commun. 2003, 2246-2247.
43. (b) Pratt, M. D.; Beer, P. D. Polyhedron 2003, 22, 649-653.
44. (c) Dudic, M.; Lhotak, P.; Stilbor, I.; Lang, K.; Proskova, P. Org. Lett. 2003, 5, 149-152.
45. (a) Tumcharem, G.; Tuntulani, T.; Coles, S. J.; Hursthouse, M. B.; Kilburn, J. D. Org. Lett. 2003, 26, 4971-4974.
46. (b) Kondo, S.; Nagamine, M.; Yano, Y. Tetrahedron Lett. 2003, 44, 8801-8804.
47. (c) Lam, C.-K.; Mak, T. C. W. Chem. Commun. 2003, 2660-2661.
48. (a) Tobey, S. L.; Anslyn, E. V. J. Am. Chem, Soc. 2003, 125, 14 807-14 815.
49. (b) Tobey, S. L.; Jones, B. D.; Anslyn, E. V. J. Am. Chem. Soc. 2003, 125, 4026-4027.
50. (c) Wiskur, S. L.; Floriano, P. N.; Anslyn, E. V.; McDevitt, J. T. Angew. Chem., Int. Ed. 2003, 42, 2070-2072.
51. (d) Best, M. D.; Tobey, S. L.; Anslyn, E. V. Coord. Chem. Rev. 2003, 240, 3-15.
52. (a) Hancock, R. D.; Martell, A. E. Chem. Rev. 1989, 89, 1875-1914.
53. (b) Busch, D. Chem. Rev. 1993, 93, 847-860.
54. (c) Martell, A. E.; Hancock, R. D. Metal Complexes in Aqueous Solution; Fackler, J. F., Jr., Ed.; Plenum Press: New York, 1996.
55. (d) Hay, B. P.; Hancock, R. D. Coord. Chem. Rev. 2001, 212, 61-78.
56. Jeffrey, G. A. An Introduction to Hydrogen Bonding; Truhlar, D. G., Ed.; Oxford University Press: Oxford, 1997.
57. Desiraju, G. R.; Steiner, T. The Weak Hydrogen Bond in Structural Chemistry and Biology; Oxford University Press: Oxford, 1999.
58. Hay, B. P.; Dixon, D. A.; Bryan, J. C.; Moyer, B. A. J. Am. Chem. Soc. 2002, 124, 182-183.
59. (a) Taylor, R.; Kennard, O. J. Am. Chem. Soc. 1982, 104, 5063-5070.
60. (b) Taylor, R.; Kennard, O.; Versichel, W. J. Am. Chem. Soc. 1983, 105, 5761-5766.
61. (c) Murray-Rust, P.; Glusker, J. P. J. Am. Chem. Soc. 1984, 106, 1018-1025.
62. (d) Steiner, T.; Kanters, J. A.; Kroon J. Chem. Commun. 1996, 1277-1278.
63. (e) Steiner, T. Chem. Commun. 1997, 727-734.
64. (a) Allen, F. H.; Kennard, O.; Taylor, R. Acc. Chem. Res. 1983, 16, 146-153.
65. (b) Allen, F. H.; Davies, J. E.; Galloy, J. J.; Johnson, O.; Kennard, O.; Macrae, C. F.; Mitchell, E. M.; Smith, J. M.; Watson, D. G. J. Chem. Inf. Comput. Sci. 1991, 31, 187-204.
66. (c) Allen, F. H.; Kennard, O. Chemical Design Automation News 1993, 8, 31-37.
67. (a) Parr R. G.; Yang, W. in Density Functional Theory of Atoms and Molecules; Oxford University Press: Oxford. 1989.
68. (b) Density Functional Methods in Chemistry; Labanowski, J. K., Andzelm, J. W., Eds.; Springer-Verlag: New York, 1991.
69. (a) Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618-620.
70. (b) Pople, J. A.; Binkley, J. S.; Seeger, R. Int. J. Quantum Chem. Symp. 1976, 10, 1-10.
71. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
72. Perdew, J. P. Phys Rev. B 1986, 33, 8822-8824.
73. MacSpartan Pro User's Guide; WaveFunction, Inc.: Irvine, California; 2000, http://www.wavefun.com.
74. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
75. Godbout, N.; Salahub, D. R.; Andzelm, J.; Wimmer, E. Can. J. Chem. 1992, 70, 560-571.
76. (a) Bernholdt, D. E.; Apra, E.; Fruchtl, H. A.; Guest, M. F.; Harrison, R. J.; Kendall, R. A.; Kutteh, R. A.; Long, X.; Nicholas, J. B.; Nichols, J. A.; Taylor, H. L.; Wong, A. T.; Fan, G. I.; Littlefield, R. J.; Nieplocha, J. Int. J. Quantum Chem. Symp. 1995, 29, 475-483.
77. (b) Harrison, R. J.; Nichols, J. A.; Straatsma, T. P.; Dupuis, M.; Bylaska, E. J.; Fann, G. I.; Windus, T. L.; Aprà, E.; Anchell, J.; Bernholdt, D.; Borowski, P.; Clark, T.; Clerc, D.; Dachsel, H.; de Jong, B.; Deegan, M.; Dyall, K.; Elwood, D.; Fruchtl, H.; Glendenning, E.; Gutowski, M.; Hess, A. C.; Jaffe, J.; Johnson, B.; Ju, J.; Kendall, R. A.; Kobayashi, R.; Kutteh, R.; Lin, Z.; Littlefield, R.; Long, X.; Meng, B.; Nieplocha, J.; Niu, S.; Rosing, M.; Sandrone, G.; Stave, M.; Taylor, H.; Thomas, G. van Lenthe, J.; Wolinski, K.; Wong, A.; Zhang, Z. MWChem, A Computational Chemistry Package for Parallel Computers, version 4.0.1; William, R., Ed.; Wiley Environmental Molecular Sciences Laboratory, Pacific Northwest National Laboratory: Richland, WA, 99352-0999, USA, 2001.
78. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 98, revision A.4.; Gaussian, Inc.: Pittsburgh, PA, 1998.
79. (a) Chandra, A. K.; Nguyen, M. T.; Uchimaru, T.; Zeegers-Huyskens, T. J. Phys. Chem. A 1999, 103, 8853-8860.
80. (b) Okhissi, A.; Adamowicz, L.; Maes, G. J. Phys. Chem. A 2000, 104, 2112-2119.
81. (c) Rak, J.; Skurski, P.; Simons, J.; Gutowski, M. J. Am. Chem. Soc. 2001, 123, 11 695-11 707.
82. (d) Skurski, P.; Rak, J.; Simons, J.; Gutowski, M. J. Am. Chem. Soc. 2001, 123, 11073-11074.
83. (e) Kryachko, E. S.; Nguyen, M. T.; Zeegers-Huyskens, T. J. Phys. Chem. A, 2001, 105, 1934-1943.
84. (f) Dabkowska, I.; Rak, J.; Gutowski, M. J. Phys. Chem. A 2002, 106, 7423-7433.
85. (a) Dunning, T. H., Jr. J. Chem. Phys. 1989, 90, 1007-1023.
86. (b) Kendall, R. A.; Dunning, T. H., Jr.; Harrison, R. S. J. Chem. Phys. 1992, 96, 6796-6806.
87. (a) Peterson, K. A.; Woon, D. E.; Dunning, T. H., Jr. J. Chem. Phys. 1994, 100, 7410-7415.
88. (b) Woon, D. E.; Dunning, T. H., Jr. J. Chem. Phys. 1994, 101, 8877-8893.
89. (a) Vargas, R.; Garza, J.; Dixon, D. A.; Hay, B. P. J. Am. Chem. Soc. 2000, 122, 4750-4755.
90. (b) Vargas, R.; Garza, J.; Friesner, R. A.; Stern, H.; Hay, B. P.; Dixon, D. A. J. Phys. Chem. A 2001, 105, 4963-4968.
91. (c) Vargas, R.; Garza, J.; Hay, B. P.; Dixon, D. A. J. Phys. Chem. A 2002, 106, 3213-3218.
92. Steiner, T. Crystallogr. Rev. 1996, 6, 1-57.
93. Camaioni, D. M.; Dupuis, M. Bentley, J. J. Phys. Chem. A 2003, 107, 5778-5788.
94. Howell, J. M.; Sapse, A. M.; Singman, E.; and Snyder, G. J. Phys. Chem. 1982, 86, 2345-2349.
95. Shen, M.; Xie, Y.; Schaefer, H. F.; Deakyne, C. A. J. Chem. Phys. 1990, 93, 3379-3388.
96. Waterland, M. R.; Stockwell, D.; Kelley, A. M. J. Chem. Phys. 2001, 114, 6249-6258.
97. Ebner, C.; Sansone, R.; Probst, M. Int. J. Quantum Chem. 1998, 70, 877-886.
98. Wang, X.-B.; Yang, X.; Wang, L.-S.; Nicholas, J. B. J. Chem. Phys. 2002, 116, 561-570.
99. Fritsky, I. O., Swiatek-Kozlowska, J.; Kapshuk, A. A.; Kozlowski, H.; Sliva, T. Yu.; Gumienna-Kontecka, E.; Prisyazhnaya, E. V.; Iskenderov, T. S. Z. Naturforsch., Teil B 2000, 55, 966-970.
100. (a) Rovira. M. C.; Novoa, J. J.; Whangbo, M.-H.; Williams, J. M. Chem. Phys. 1995, 200, 319-335.
101. (b) Gu, Y.; Kar, T.; Scheiner, S. J. Am. Chem. Soc. 1999, 121, 9411-9422.
102. (c) Novoa, J. J.; Mota, F. Chem. Phys. Lett. 1997, 266, 23-30.
103. (d) Kim, K. S.; Friesner, R. A. J. Am. Chem. Soc. 1997, 119, 12952-12961.
104. -1): (a) OH-, 390.3 ± 0.3, Schulz, P. A.; Mead, R. D.; Jones, P. L.; Lineberger, W. C. J. Chem. Phys. 1982, 77, 1153-1165.
105. -, 382 ± 1, Ramond, T. M.; Davico, G. E.; Schwartz, R. L.; Lineberger, W. C. J. Chem. Phys. 2000, 112, 1158-1169.
106. -, 360.4 ± 2.1, Taft, R. W. Prog. Phys. Org. Chem. 1987, 16, 1.
107. -, 418.0 ± 3.5, Graul, S. T.; Squires, R. R. J. Am. Chem. Soc. 1990, 112, 2517-2529.
108. 42b calculations yield a repulsive interaction energy of 16.8 kcal/mol.
109. (b) Allinger, N. L.; Yuh, Y. H.; Lii, J.-H. J. Am. Chem. Soc. 1989, 111, 8551-8566.
110. Prins, R.; de Graaff, R. A. G.; Haasnoot, J. G.; Vader, C.; Reedijk, J. J. Chem. Soc. Chem. Commun. 1986, 1430-1431.
111. Smith, G. T.; Mallinson, P. R.; Frampton, C. S.; Farrugia, L. J.; Peacock, R. D.; Howard, J. A. K. J. Am. Chem. Soc. 1997, 119, 5028-5034.
112. Rosenstein, R. D.; Oberding, M.; Hyde, J. R.; Zubieta, J.; Karlin, K. D.; Seeman, N. C. Cryst. Struct. Commun. 1982, 11, 1507-1513.
113. Ahrens, B.; Cotton, S. A.; Feeder, N.; Noy, O. E.; Raithby, P. R.; Teat, S. J. J. Chem. Soc., Dalton Trans. 2002, 2027-2030.
114. Mostad, A.; Natarajan, S. Z. Kristallogr. 1985, 172, 175-182.
115. Goodgame, D. M. L.; Newnham, S.; O'Mahoney, C. A.; Williams, D. J. Polyhedron 1990, 9, 491-494.
116. Lauri, G.; Bartlett, P. A. J. Comput. Aided. Mol. Design 1994, 8, 51-66.
117. (a) Hay, B. P.; Firman, T. K. Inorg. Chem. 2002, 41, 5502-5512.
118. (b) Hay, B. P.; Firman, T. K. HostDesigner User's Manual; Pacific Northwest National Laboratory: Richland, Washington, 2003, http://hostdesigner. emsl.pnl.gov.
119. (a) Dietrich, B.; Fyles, T. M.; Lehn, J. M.; Pease, L. G.; Fyles, D. L J. Chem. Soc. Chem. Commun. 1978, 934-936.
120. (b) Dietrich, B.; Fyles, D. L.; Fyles, T. M.; Lehn, J. M. Helv. Chim. Acta 1979, 62, 2763-2787.
121. Herges, R.; Dikmaus, A.; Jana, U.; Köhler, F.; Jones, P. G.; Dix, I.; Fricke, T.; König, B. Eur. J. Org. Chem. 2002, 3004-3014.