Density functional theory study of a molecular allosteric switch for 2,2′-bipyridyl-3,3′-15-crown-5

Journal of Computational Chemistry

Volumn 32, Issue 3, 2011, Pages 406-415

  Miao, Yuan ^a   Wang, Xueye ^a   Jin, Xin ^a   Yi, Ling ^a   Ren, Cuihuan ^a  

^a XIANGTAN UNIVERSITY   (China)

Author keywords

2,2 bipyridyl 3, 3 15 crown 5; allosteric switch; density functional theory (DFT); preorganization

Indexed keywords

ACTIVE SITE; ALKALI METAL CATIONS; ALLOSTERIC SWITCH; ALLOSTERISM; B3LYP/6-31G; BIPYRIDYL; CATION EXCHANGES; CHARGE TRANSFER INTERACTION; CLASSICAL MODEL; DENSITY FUNCTIONAL THEORY (DFT); DENSITY FUNCTIONAL THEORY METHODS; DRESDENS; EFFECTIVE CORE POTENTIAL; FUKUI FUNCTIONS; INTERNAL FORCES; MOLECULAR MACHINES; MOLECULAR SWITCHES; NATURAL BOND ORBITAL ANALYSIS; NUCLEOPHILICITIES; OPTIMIZED GEOMETRIES; PREORGANIZATION; TARGET MOLECULE;

BINDING ENERGY; BIOCHEMISTRY; CHARGE TRANSFER; CHEMICAL BONDS; COMPLEXATION; CROWN ETHERS; POSITIVE IONS; THERMODYNAMIC PROPERTIES; TUNGSTEN; TUNGSTEN COMPOUNDS;

DENSITY FUNCTIONAL THEORY;

EID: 78650508176     PISSN: 01928651     EISSN: 1096987X     Source Type: Journal    
DOI: 10.1002/jcc.21627     Document Type: Article

References (66)

1. Lehn, J. M., Science 1993, 260, 1762.
2. Lehn, J. M., Supramolecular Chemistry; Wiley-VCH: Weinheim, 1995.
3. Pedersen, C. J., J Am Chem Soc 1967, 89, 2495.
4. Pedersen, C. J., Angew Chem Int Ed Engl 1988, 27, 1021.
5. Cram, D. J., Angew Chem Int Ed Engl 1988, 27, 1009.
6. Lehn, J. M., Angew Chem Int Ed Engl 1988, 27, 89.
7. Lehn, J. M., Struct Bonding (Berlin) 1973, 16, 1.
8. Lehn, J. M., Pure Appl Chem 1978, 50, 871.
9. Lehn, J. M., Pure Appl Chem 1979, 51, 979.
10. Lehn, J. M., Acc Chem Res 1978, 11, 49.
11. Kyba, E. P.,;, Helgeson, R. C.,;, Madan, K.,;, Gokel, G. W.,;, Tarnowski, T. L.,;, Moore, S. S., Cram, D. J., J Am Chem Soc 1977, 99, 2564.
12. Kovbasyuk, L.,;, Krämer, R., Chem Rev 2004, 104, 3161.
13. Rebek, J., Jr.,;, Trend, J. E.,;, Wattley, R. V.,;, Chakravorti, S., J Am Chem Soc 1979, 101, 4333.
14. Rebek, J., Jr.,;, Wattley, R. V., J Am Chem Soc 1980, 102, 4853.
15. Rebek, J., Jr.,;, Marshall, L., J Am Chem Soc 1983, 105, 6668.
16. Schmittel, M.,;, Lin, H. W., Angew Chem 2007, 119, 911.
17. Rebek, J., Jr., Acc Chem Res 1984, 17, 258.
18. Becke, A. D., J Chem Phys 1993, 98, 5648.
19. Lee, C.,;, Yang, W.,;, Parr, R. G., Phys Rev B 1988, 37, 785.
20. Korth, H. G.,;, De Heer, M. I.,;, Mulder, P., J Phys Chem A 2002, 106, 8779.
21. Johnson, B. G.,;, Gill, P. M. W.,;, Pople, J. A., J Chem Phys 1993, 98, 5612.
22. Chowdhury, P. K., J Phys Chem A 2003, 107, 5692.
23. Chis, V., J Chem Phys 2004, 300, 1.
24. Asensio, A.,;, Kobko, N.,;, Dannenberg, J. J., J Phys Chem A 2003, 107, 6441.
25. Müller, A.,;, Losada, M.,;, Leutwyler, S., J Phys Chem A 2004, 108, 157.
26. Goncalves, N. S.,;, Cristiano, R.,;, Pizzolatti, M. G.,;, da Silva Miranda, F., J Mol Struct 2005, 733, 53.
27. 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.,;, 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. M.,;, Al-Laham, A.,;, Peng, C. Y.,;, Nanayakkara, A.,;, Challacombe, M. P.,;, Gill, M. W.,;, Johnson, B.,;, Chen, W.,;, Wong, M. W.,;, Gonzalez, C.,;, Pople, J. A., Gaussian 2003W Revision B.05; Gaussian Inc.: Pittsburgh, 2003.
28. Hirva, P.,;, Haukka, M.,;, Jakonen, M.,;, Moreno, M. A., J Mol Model 2008, 14, 171.
29. Andrae, D.,;, Hauessermann, U.,;, Dolg, M.,;, Stoll, H.,;, Preuss, H., Theor Chim Acta 1990, 77, 123.
30. Reed, A. E.,;, Curtiss, L. A.,;, Weinhold, F., Chem Rev 1988, 88, 899.
31. Reed, A. E.,;, Weinhold, F., J Chem Phys 1983, 78, 4066.
32. Foster, J. P.,;, Weinhold, F., J Am Chem Soc 1980, 102, 7211.
33. Reed, A. E.,;, Weinstock, R. B.,;, Weinhold, F., J Chem Phys 1985, 83, 735.
34. Parr, R. G.,;, Yang, W., J Am Chem Soc 1984, 106, 4049.
35. Yang, W.,;, Mortier, W. J., J Am Chem Soc 1986, 108, 5708.
36. More, M. B.,;, Glendening, E. D.,;, Ray, D.,;, Feller, D.,;, Armentrout, P. B., J Phys Chem 1996, 100, 1605.
37. Hill, S. E.,;, Glendening, E. D.,;, Feller, D., J Phys Chem A 1997, 101, 6125.
38. Hill, S. E.,;, Feller, D.,;, Glendening, E. D., J Phys Chem A 1998, 102, 3813.
39. Weber, E.,;, Vogtle, F., Top Curr Chem 1981, 98, 1.
40. Lees, A. J., Coord Chem Rev 1998, 177, 3.
41. Van Staveren, D. R.,;, Metzler-Nolte, N., Chem Commun 2002, 1406.
42. Metzler-Nolte, N., Angew Chem Int Ed Engl 2001, 40, 1040.
43. Balzani, V.,;, Juris, A.,;, Venturi, M.,;, Campagna, S.,;, Serroni, S., Chem Rev 1996, 96, 759
44. Vlcek, A., Jr., Coord Chem Rev 2002, 230, 225.
45. Hill, S. E.,;, Feller, D., Int J Mass Spectrom 2000, 201, 41.
46. Anderson, J. D.,;, Paulsen, E. S.,;, Dearden, D. V., Int J Mass Spectrom 2003, 227, 63.
47. Bagatur'yants, A. A.,;, Freidzon, A. Y.,;, Alfimov, M. V.,;, Baerends, E. J.,;, Howard, J. A. K.,;, Kuz'mina, L. G., J Mol Struct (Theochem) 2002, 588, 55.
48. Okano, K.,;, Tsukube, Hori, K., Tetrahedron 2004, 60, 10877.
49. Freidzon, A. Y.,;, Vladimirova, D. G.,;, Bagatur'yants, A. A.,;, Gromov, S. P.,;, Alfimov, M. V., J Mol Struct (Theochem) 2007, 809, 61.
50. Stufkens, D. J., Coord Chem Rev 1990, 104, 39.
51. Adamovic, I.,;, Gordon, M. S., J Phys Chem A 2005, 109, 1629.
52. Glaser, R.,;, Horan, C. J., Can J Chem 1996, 74, 1200.
53. Glaser, R.,;, Horan, C.,;, Nelson, E.,;, Hall, M. K., J Org Chem 1992, 57, 215.
54. Mo, Y.,;, Wu, W.,;, Song, L.,;, Lin, M.,;, Zhang, Q.,;, Gao, J., Angew Chem Int Ed Engl 2004, 43, 1986.
55. Mo, Y.,;, Jiao, H.,;, Schleyer, P. V. R., J Org Chem 2004, 69, 3493.
56. Mo, Y.,;, Schleyer, P. V. R.,;, Wu, W.,;, Lin, M., Zhang, Q.,;, Gao, J., J Phys Chem A 2003, 107, 10011.
57. Weinhold, F.,;, Landis, C. R., Valency and Bonding-A Natural Bond Orbital Donor-Acceptor Perspective; Cambridge University Press: Cambridge, 2005.
58. Chatfield, D.,;, Cramer, C. J., Essentials of Computational Chemistry: Theories and Models, 2nd ed.; Wiley: New York, 2002.
59. Kim, K. S.,;, Tarakeshwar, P.,;, Lee, J. Y., Chem Rev 2000, 100, 4145.
60. Boys, S. F.,;, Bernardi, F., Mol Phys 1970, 19, 553.
61. Shchori, E.,;, Nae, N.,;, Jagur-Grodzinski, J., J Chem Soc Dalton Trans 1975, 2381.
62. Kolthoff, I. M.,;, Chantooni, M. K., Anal Chem 1980, 52, 1039.
63. Hofmanova, A.,;, Koryta, J.,;, Brezine, M.,;, Mitall, M., Inorg Chim Acta 1978, 28, 73.
64. Hopkins, H. P., Jr.,;, Norman, A. B., J Phys Chem 1980, 84, 309.
65. Smetana, A. J.,;, Popov, A. I., J Solution Chem 1980, 9, 183.
66. Lamb, J. D.,;, Izatt, R. M.,;, Swain, C. S.,;, Christensen, J. J., J Am Chem Soc 1980, 102, 475.