Tailoring the key in a molecular lock-and-key model system: The propylene oxide⋯2-fluoroethanol complex

Journal of the American Chemical Society

Volumn 130, Issue 18, 2008, Pages 5916-5921

  Borho, Nicole ^a   Xu, Yunjie ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; CONFORMATIONS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; MOLECULAR VIBRATIONS; PROPYLENE;

CONFORMATIONAL ISOMERISM; FLUOROETHANOL COMPLEXES; FOURIER-TRANSFORM MICROWAVE SPECTROSCOPY; PROPYLENE OXIDE;

MOLECULAR MODELING;

2 FLUOROETHANOL; ALCOHOL DERIVATIVE; PROPYLENE OXIDE;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; HYDROGEN BOND; SPECTROSCOPY;

EPOXY COMPOUNDS; ETHANOL; ISOMERISM; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; QUANTUM THEORY; SPECTRUM ANALYSIS; THERMODYNAMICS;

EID: 42949145972     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0783411     Document Type: Article

References (58)

1. Suhm, M. Phys. Chem. Chem. Phys. 2007, 9, 4443.
2. Fischer, E. Chem. Ber. 1894, 27, 2985.
3. Allen, F. H.; Bellard, S.; Brice, M. D.; Cartwright, B. A.; Doubleday, A.; Higgs, H.; Hummelink, T.; Hummelink-Peters, B. G.; Kennard, O.; Motherwell, W. D. S.; Rodgers, J. R.; Watson, D. G. Acta Crystallogr. 1979, B35, 2331-2339.
4. Bernstein, F. C.; Koetzle, T. F.; Williams, G. J. B., Jr.; Meyer, E. F.; Brice, M. D.; Rogers, J. R.; Kennard, O.; Shimanouchi, T.; Tasumi, M. J. Mol. Biol., 1977, 112, 535-542.
5. Nicklaus, M. C.; Wang, S.; Driscoll, J. S.; Milne, G. W. A. Bioorg. Med. Chem. 1995, 3 (4), 411-428.
6. Perola, E.; Charifson, P. S. J. Med. Chem. 2004, 47, 2499-2510.
7. Koshland, D. E., Jr Proc. Natl. Acad. Sci., U.S.A. 1958, 44, 98-104.
8. Jorgensen, W. L. Science 1991, 254, 954-955.
9. Borho, N.; Xu, Y. Angew. Chem. 2007, 119, 2326-2329.
10. Angew. Chem., Int. Ed. 2007, 46, 2276-2279.
11. Maienfisch, P.; Hall, R. G. Chimia 2004, 58 (3), 93-99.
12. Povey, J. F.; Smales, C. M.; Hassard, St. J.; Howard, M. J. J. Struct. Biol. 2007, 157, 329-338.
13. (a) Buck, M. Q. Rev. Biophys. 1998, 31 (3), 297-355.
14. (b) Scharge, T.; Cézard, C.; Ziehlke, P.; Schütz, A.; Emmeluth, C.; Suhm, M. A. Phys. Chem. Chem. Phys. 2007, 9, 4472-4490.
15. (c) Fioroni, M.; Diaz, M. D.; Burger, K.; Berger, S. J. Am. Chem. Soc. 2002, 124, 7737-7744.
16. Pauling, L., The Nature of the Chemical Bond, 3rd ed.; Cornell University:, Ithica, NY, 1960.
17. Desiraju, G. R, Steiner, T., The Weak Hydrogen Bond, Oxford University Press, Oxford, U.K., 1999.
18. Craig, D. P.; Mellor, D. P. Top. Curr. Chem. 1976, 63, 1-48.
19. (a) Balle, T. J.; Flygare, W. H. Rev. Sci. Instrum. 1981, 52, 33-45.
20. (b) Andresen, U.; Dreizler, H.; Grabow, J.-U.; Stahl, W. Rev. Sci. Instrum. 1990, 61, 3694-3699.
21. Xu, Y.; Jäger, W. J. Chem. Phys., 1997, 106, 7968-7980.
22. Frisch, M. J.; et al., Gaussian 03, revision B.01; Gaussian Inc.: Pittsburgh, PA, 2003.
23. Binkley, J. S.; Pople, J. A. Int. Quantum Chem. 1975, 9, 229-236.
24. Krishman, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650-654.
25. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 10, 553-566.
26. Swalen, J. D.; Herschbach, D. R. J. Chem. Phys. 1957, 27, 100-108.
27. Herschbach, D. R.; Swalen, J. D. J. Chem. Phys. 1958, 29, 761-776.
28. No splitting due to the methyl internal rotation of propylene oxide was detected in all the transitions observed. We therefore assume that this motion is quenched in the complex owing to the strong intermolecular interactions that elevate the internal rotation barrier.
29. Creswell, R. A.; Schwendeman, R. H. J. Mol. Spectrosc. 1977, 64, 295-301.
30. Imachi, M.; Kuczkowski, R. L. J. Mol. Struct. 1982, 96, 55-60.
31. Scharge, T.; Emmeluth, C.; Häber, Th.; Suhm, M. A. J. Mol. Struct. 2006, 786, 86-95.
32. Huang, J.; Hedberg, K. J. Am. Chem. Soc. 1989, 111, 6909-6913.
33. Buckton, K.; Azrak, R. G. J. Chem. Phys. 1970, 52 (11), 5652-5655.
34. Buckley, P.; Giguère, P. A.; Yamamoto, D. Can. J. Chem. 1968, 46, 2917-2923.
35. Bakke, J. M.; Bjerkeseth, L. H.; Rønnow, T. E. C. L.; Steinsvoll, K. J. Mol. Struct. 1994, 321, 205-214.
36. Gounev, T. K.; Bell, S.; Zhou, L.; Durig, J. R. J. Mol. Struct., 1998, 447, 21-32.
37. Frei, H.; Pimentel, G. C. Annu. Rev. Phys. Chem. 1985, 36, 491-524.
38. Pourcin, J.; Monnier, M.; Verlaque, P.; Davidovics, G.; Lauricella, R.; Colonna, C.; Bodot, H. J. Mol. Spectrosc. 1985, 109, 186-201.
39. Shirk, J. S.; Marquardt, C. L. J. Chem. Phys., 1990, 92 (12), 7234-7240.
40. Green, D.; Hammond, S.; Keske, J.; Pate, B. H. J. Chem. Phys. 1999, 110 (4), 1979-1989.
41. Radom, L.; Lathan, W. A.; Hehre, W. J.; Pople, J. A. J. Am. Chem. Soc. 1973, 95 (3), 693-698.
42. Dixon, D. A.; Smart, B. E. J. Phys. Chem. 1991, 95, 1609-1612.
43. Buemi, G. J. Chem. Soc., Faraday Trans. 1994, 90 (9), 1211-1215.
44. Wolfe, S. Acc. Chem. Res. 1972, 5, 102-111.
45. Freitas, M. P.; Rittner, R. J. Phys. Chem. A 2007, 111, 7233-7236.
46. Blanco, S.; Maris, A.; Melandri, S.; Caminati, W. Mol. Phys. 2002, 100, 3245-3249.
47. Su, Z.; Xu, Y. J. Mol. Spectrosc. 2005, 232, 112-114.
48. Su, Z.; Borho, N.; Xu, Y. J. Am. Chem. Soc. 2006, 128, 17126-17131.
49. Szalewicz, K.; Jeziorski, B. J. Chem. Phys. 1998, 109 (3), 1198-1200.
50. Xantheas, S. J. Chem. Phys. 1996, 104, 8821-8824.
51. Borho, N.; Xu, Y. Phys. Chem. Chem. Phys. 2007, 9, 4514-4520.
52. Connell, L. L.; Corcoran, T. C.; Joireman, P. W.; Felker, P. M. J. Phys. Chem. 1990, 94, 1229-1232.
53. Carney, J. R.; Dian, B. C.; Florio, G. M.; Zwier, T. S. J. Am. Chem. Soc. 2001, 123, 5596-5597.
54. Schmitt, M.; Böhm, M.; Ratzer, C.; Vu, C.; Kalkman, I.; Meerts, W. L. J. Am. Chem. Soc. 2005, 127, 10356-10364.
55. (a) Nguyen, T. V.; Pratt, D. W. J. Chem. Phys. 2006, 124, 054317-1-054317-6.
56. (b) Nguyen, T. V.; Korter, T. M.; Pratt, D. W. Mol. Phys. 2005, 103, 1603-1613.
57. Portmann, S.; Inauen, A.; Lüthi, H. P.; Leutwyler, S. J. Chem. Phys. 2000, 113, 9577-9585.
58. Giardini, A.; Cattenacci, G.; Paladini, A.; Piccirillo, S.; Satta, M.; Rondino, F.; Speranza, M. J. Phys. Chem. A 2007, 111, 12559-12563.