Solid-state 23Na NMR study of sodium lariat ether receptors exhibiting cation - π interactions

Journal of Physical Chemistry A

Volumn 110, Issue 50, 2006, Pages 13568-13577

  Bryce, David L ^a   Adiga, Samyuktha ^a   Elliott, Elizabeth K ^b   Gokel, George W ^b  

^a UNIVERSITY OF OTTAWA   (Canada)

^b WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE RING; MAGIC-ANGLE SPINNING (MAS); QUADRUPOLAR COUPLING CONSTANTS; QUANTUM CHEMICAL CALCULATIONS; SOLID-STATE NUCLEAR MAGNETIC RESONANCE (SSNMR);

AMINO ACIDS; BIOCHEMISTRY; ELECTRIC FIELD EFFECTS; ETHERS; NUCLEAR MAGNETIC RESONANCE; SODIUM COMPOUNDS; SUPRAMOLECULAR CHEMISTRY; TENSORS;

POSITIVE IONS;

ETHER DERIVATIVE; MONOVALENT CATION; SODIUM;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; QUANTUM THEORY;

CATIONS, MONOVALENT; ETHERS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; QUANTUM THEORY; SODIUM;

EID: 33846677334     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp065171q     Document Type: Article

References (84)

1. Gokel, G. W. Chem. Commun. 2003, 2847.
2. De Wall, S. L.; Barbour, L. J.; Gokel, G. W. J. Am. Chem. Soc. 1999, 121, 8405.
3. De Wall, S. L.; Meadows, E. S.; Barbour, L. J.; Gokel, G. W. J. Am. Chem. Soc. 1999, 121, 5613.
4. Hu, J.; Barbour, L. J.; Gokel, G. W. Chem. Commun. 2001, 1858.
5. Hu, J.; Barbour, L. J.; Gokel, G. W. Collect. Czech. Chem. Commun. 2004, 69, 1050.
6. Hu, J.; Barbour, L. J.; Gokel, G. W. J. Am. Chem. Soc. 2001, 123, 9486.
7. Sunner, J.; Nishizawa, K.; Kebarle, P. J. Phys. Chem. 1981, 85, 1814.
8. Guo, B. C.; Purnell, J. W.; Castleman, A. W., Jr. Chem. Phys. Lett. 1990, 168, 155.
9. Ma, J. C.; Dougherty, D. A. Chem. Rev. 1997, 97, 1303.
10. Gokel, G. W.; De Wall, S. L.; Meadows, E. S. Eur. J. Org. Chem. 2000, 2967.
11. Scrutton, N. S.; Raine, A. R. C. Biochem. J. 1996, 319, 1.
12. Dougherty, D. A. Science 1996, 271, 163.
13. Biot, C.; Buisine, E.: Rooman, M. J. Am. Chem. Soc. 2003, 125, 13988.
14. Shi, Z.; Olson, C. A.; Kallenbach, N. R. J. Am. Chem. Soc. 2002, 124, 3284.
15. Crowley, P. B.; Golovin, A. Proteins: Struct., Funct., Bioinf. 2005, 59, 231.
16. Biot, C.; Wintjens, R.; Rooman, M. J. Am. Chem. Soc. 2004, 126, 6220.
17. Wintjens, R.; Lievin, J.; Rooman, M.; Buisine, E. J. Mol. Biol. 2000, 302, 395.
18. Gallivan, J. P.; Dougherty, D. A. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 9459.
19. Gromiha, M. M.; Santhosh, C.; Suwa, M. Polymer 2004, 45, 633.
20. Choi, H. S.; Suh, S. B.; Cho, S. J.; Kim, K. S. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 12094.
21. McFail-Isom, L.; Shui, X.; Williams, L. D. Biochemistry 1998, 37, 17105.
22. Šponer, J.; Leszczynski, J.; Hobza, P. Biopolymers 2002, 61, 3.
23. Primet, M.; Garbowski, E.; Mathieu, M. V.; Imelik, B. J. Chem. Soc., Faraday Trans. 1 1980, 76, 1942.
24. Hashimoto, S.; Ikuta, S.; Asahi, T.; Masuhara, H. Langmuir 1998, 14, 4284.
25. Mentzen, B. R.; Gélin, P. Mater. Res. Bull. 1998, 33, 109.
26. Zhu, D.; Herbert, B. E.; Schlautman, M. A.; Carraway, E. R. J. Environ. Qual. 2004, 33, 276.
27. Goshe, A. J.; Crowley, J. D.; Bosnich, B. Helv. Chim. Acta 2001, 84, 2971.
28. Klärner, F.-G.; Kahlert, B. Acc. Chem. Res. 2003, 36, 919.
29. Cametti, M.; Nissinen, M.; Cort, A. D.: Mandolini, L.; Rissanen, K. J. Am. Chem. Soc. 2005, 127, 3831.
30. Reddy, A. S.; Sastry, G. N. J. Phys. Chem. A 2005, 109, 8893.
31. Woodin, R. L.; Beauchamp, J. L. J. Am. Chem. Soc. 1978, 100, 501.
32. Gokel, G. W.; Barbour, L. J.; De Wall, S. L.; Meadows, E. S. Coord. Chem. Rev. 2001, 222, 127.
33. De Wall, S. L.; Meadows, E. S.; Barbour, L. J.; Gokel, G. W. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 6271.
34. Meadows, E. S.; De Wall, S. L.; Barbour, L. J.; Gokel, G. W. J. Am. Chem. Soc. 2001, 123, 3092.
35. Gokel, G. W.; Barbour, L. J.; Ferdani, R.; Hu, J. Acc. Chem. Res. 2002, 35, 878.
36. Hu, J.; Barbour, L. J.; Ferdani, R.; Gokel, G. W. Chem. Commun. 2002, 1806.
37. Hu, J.; Barbour, L. J.; Gokel, G. W. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5121.
38. Isupov, M. N.; Antson, A. A.; Dodson, E. J.; Dodson, G. G.; Dementieva, I. S.; Zakomirdina, L. N.; Wilson, K. S.; Dauter, Z.; Lebedev, A. A.; Harutyunyan, E. H. J. Mol. Biol. 1998, 276, 603.
39. Frydman, L. Annu. Rev. Phys. Chem. 2001, 52, 463.
40. Ashbrook, S. E.; Duer, M. J. Concepts Magn. Reson. 2006, 28A, 183.
41. Power, W. P.; Wasylishen, R. E.; Mooibroek, S.; Pettitt, B. A.; Danchura, W. J. Phys. Chem. 1990, 94, 591.
42. Chu, P. J.; Gerstein, B. C. J. Chem. Phys. 1989, 91, 2081.
43. Matthews, S. E.; Rees, N. H.; Felix, V.; Drew, M. G. B.; Beer, P. D. Inorg. Chem. 2003, 42, 729.
44. Lhotak, P.; Nakamura, R.; Shinkai, S. Supramol. Chem. 1997, 8, 333.
45. Wong, A.; Whitehead, R. D.; Gan, Z.; Wu, G. J. Phys. Chem. A 2004, 108, 10551.
46. Watts, A. Mol. Membr. Biol. 2002, 19, 267.
47. Williamson, P. T. F.; Meier, B. H.; Watts, A. Eur. Biophys. J. 2004, 33, 247.
48. Zhong, W.; Gallivan, J. P.; Zhang, Y.; Li, L.; Lester, H. A.; Dougherty, D. A. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 12088.
49. Dumazy, Y.; Amoureux, J.-P.; Fernandex, C. Mol. Phys. 1997, 90, 959.
50. Bodart, P. R.; Amoureux, J.-P.; Dumazy, Y.; Lefort, R. Mol. Phys. 2000, 98, 1545.
51. Amoureux, J.-P.; Fernandez, C.; Steuernagel, S. J. Magn. Reson., Ser. A 1996, 123, 116.
52. Harris, R. K.; Nesbitt, G. J. J. Magn. Reson. 1988, 78, 245.
53. Eichele, K.; Wasylishen R. E. WSOLIDS NMR Simulation Package, version 1.17.30; Universitat Tuebingen: Tuebingen, Germany, 2001. See also http://casgm3.anorg.chemie.uni-tuebingen.de/klaus/soft/index.html.
54. Massiot, D.; Fayon, F.; Capron, M.; King, I.; Le Calvé, S.; Alonso, B.; Durand, J.-O.; Bujoli, B.; Gan, Z.; Hoatson, G. Magn. Reson. Chem. 2002, 40, 70.
55. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revisions B.04 and C.02; Gaussian, Inc.: Wallingford, CT, 2004.
56. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
57. Pyykkö, P. Mol. Phys. 2001, 99, 1617.
58. Dennington, R., II; Keith, T.; Millam, J.; Eppinnett, K.; Hovell, W. L.; Gilliland, R. GaussView, version 3.09; Semichem. Inc.: Shawnee Mission, KS, 2003.
59. Wong, A.; Wu, G. J. Phys. Chem. A 2000, 104, 11844.
60. Pietrass, T.; Burkert, P. K. Magn. Reson. Chem. 1993, 31, 709.
61. Detellier, C. In NMR of Newly Accessible Nuclei, Volume 2: Chemically and Biochemically Important Elements; Laszlo, P., Ed.; Academic Press: New York, 1983; Chapter 5.
62. Bisnaire, M.; Detellier, C.; Nadon, D. Can. J. Chem. 1982, 60, 3071.
63. Willans, M. J.; Schurko, R. W. J. Phys. Chem. B 2003, 107, 5144.
64. Samoson, A. Chem. Phys. Lett. 1985, 119, 29.
65. Hu, J.; Barbour, L. J.; Ferdani, R.; Gokel, G. W. Chem. Commun. 2002, 1810.
66. Frydman, L.; Harwood, J. S. J. Am. Chem. Soc. 1995, 117, 5367.
67. Medek, A.; Harwood, J. S.; Frydman, L. J. Am. Chem. Soc. 1995, 117, 12779.
68. Medek, A.; Frydman, L. J. Braz. Chem. Soc. 1999, 10, 263.
69. Grant, C. V.; McElheny, D.; Frydman, V.; Frydman, L. Magn. Reson. Chem. 2006, 44, 366.
70. Mason, J. Solid State Nucl. Magn. Reson. 1993, 2, 285.
71. Arfken, G. B. Mathematical Methods for Physicists; Academic Press: New York, 1985.
72. Sagnowski, S. F.; Sułek, Z.; Stachura, M.; Ogar, J. Z. Phys. B: Condens. Matter 1982, 46, 123.
73. Dunning, T. H., Jr. J. Chem. Phys. 1989, 90, 1007.
74. Woon, D. E.; Dunning, T. H., Jr. J. Chem. Phys. 1995, 103, 4572.
75. Pickard, C. J.; Mauri, F. In Calculation of NMR and EPR Parameters. Theory and Applications; Kaupp, M., Bühl, M., Malkin, V. G., Eds.; Wiley-VCH Verlag GmbH & co. KGaA: Weinheim, Germany, 2004; Chapter 16.
76. Ramsey, N. F. Molecular Beams; Oxford University Press: London, 1956; pp 162-166, 208-213.
77. Ramsey, N. F. Phys. Rev. 1950, 77, 567.
78. Ramsey, N. F. Phys. Rev. 1950, 78, 699.
79. Ramsey, N. F. Phys. Rev. 1951, 83, 540.
80. Ramsey, N. F. Phys. Rev. 1952, 86, 243.
81. Jameson, C. J. In Encyclopedia of Nuclear Magnetic Resonance; Grant, D. M., Harris, R. K., Eds.; Wiley: Chichester, U.K., 1996; p 1273.
82. Jameson, C. J. In Multinuclear NMR; Mason, J., Ed.; Plenum Press: New York, 1987; Chapter 3 and references therein.
83. Ruan, C.; Yang, Z.; Hallowita, N.; Rodgers, M. T. J. Phys. Chem. A 2005, 109, 11539.
84. Petersen, F. N. R.; Jensen, M. Ø.; Nielsen, C. H. Biophys. J. 2005, 89, 3985.