The hydrogen-bonded 2-pyridone dimer model system. 1. combined NMR and FT-IR spectroscopy study

Journal of Physical Chemistry A

Volumn 114, Issue 29, 2010, Pages 7749-7760

  Szyc, Łukasz ^a   Guo, Jing ^b   Yang, Ming ^a   Dreyer, Jens ^a   Tolstoy, Peter M ^b   Nibbering, Erik T J ^a   Czarnik Matusewicz, Bogusława ^c   Elsaesser, Thomas ^a   Limbach, Hans Heinrich ^b  

^a MAX BORN INSTITUT   (Germany)

^b FREIE UNIVERSITÄT BERLIN   (Germany)

^c UNIVERSITY OF WROC AW   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

2-HYDROXYPYRIDINE; 2-PYRIDONES; CHAIN-LIKE; COMPLEXATION CHEMISTRY; CONCENTRATION-DEPENDENT; CYCLIC DIMERS; DATA SETS; DIMER MODEL; EFFECTIVE TIME; FOURIER TRANSFORM INFRARED; FT-IR SPECTRUM; FTIR SPECTROSCOPY; H NMR SPECTRA; HIGHER TEMPERATURES; HYDROGEN-BOND FORMATION; LOW TEMPERATURES; PICOSECONDS; PROTON EXCHANGE MECHANISMS; PYRIDONES; REACTION PATHWAYS; SOLUTE-SOLVENT COMPLEXES; SPECTRAL OVERLAP; STRETCHING REGION; TEMPERATURE DEPENDENT; TWO-DIMENSIONAL IR CORRELATION SPECTROSCOPY; VIBRATIONAL TRANSITIONS;

DICHLOROMETHANE; DIMERS; FOURIER TRANSFORMS; HYDROGEN; HYDROGEN BONDS; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTONS; REACTION INTERMEDIATES; WAVELET TRANSFORMS;

COMPLEXATION;

2 HYDROXYPYRIDINE; 2-HYDROXYPYRIDINE; LACTAM; PYRIDONE DERIVATIVE; SOLVENT;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; DIMERIZATION; HYDROGEN BOND; INFRARED SPECTROSCOPY; ISOMERISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLUTION AND SOLUBILITY;

DIMERIZATION; HYDROGEN BONDING; ISOMERISM; LACTAMS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; PYRIDONES; SOLUTIONS; SOLVENTS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 77954912773     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp103630w     Document Type: Article

References (87)

1. Hobza, P.; Šponer, J. Chem. Rev. 1999, 99, 3247
2. Nir, E.; Kleinermanns, K.; de Vries, M. S. Nature 2000, 408, 949
3. Zoete, V.; Meuwly, M. J. Chem. Phys. 2004, 121, 4377
4. Bakker, J. M.; Compagnon, I.; Meijer, G.; von Helden, G.; Kabeláč, M.; Hobza, P.; de Vries, M. S. Phys. Chem. Chem. Phys. 2004, 6, 2810
5. Nir, E.; Hünig, I.; Kleinermanns, K.; de Vries, M. S. ChemPhysChem 2004, 5, 131
6. Abo-Riziq, A.; Grace, L.; Nir, E.; Kabelac, M.; Hobza, P.; de Vries, M. S. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 20
7. de Vries, M. S.; Hobza, P. Annu. Rev. Phys. Chem. 2007, 58, 585
8. Céron-Carrasco, J. P.; Requena, A.; Zúñiga, J.; Michaux, C.; Perpète, E. A.; Jacquemin, D. J. Phys. Chem. A 2009, 113, 10549
9. Céron-Carrasco, J. P.; Requena, A.; Michaux, C.; Perpète, E. A.; Jacquemin, D. J. Phys. Chem. A 2009, 113, 7892
10. Taylor, C. A.; El-Bayoumi, M. A.; Kasha, M. Proc. Natl. Acad. Sci. U.S.A. 1969, 63, 253
11. Douhal, A.; Kim, S. K.; Zewail, A. H. Nature 1995, 378, 260
12. Müller, A.; Talbot, F.; Leutwyler, S. J. Am. Chem. Soc. 2002, 124, 14486
13. Wu, R.; Brutschy, B. J. Phys. Chem. A 2004, 108, 9715
14. Roscioli, J. R.; Pratt, D. W. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 13752
15. Beak, P.; Fry, F. S., Jr. J. Am. Chem. Soc. 1973, 95, 1700
16. Beak, P.; Fry, F. S., Jr.; Lee, J.; Steele, F. J. Am. Chem. Soc. 1976, 98, 171
17. Brown, R. S.; Tse, A.; Vederas, J. C. J. Am. Chem. Soc. 1980, 102, 1174
18. Nimlos, M. R.; Kelley, D. F.; Bernstein, E. R. J. Phys. Chem. 1989, 93, 643
19. Matsuda, Y.; Ebata, T.; Mikami, N. J. Chem. Phys. 1999, 110, 8397
20. Matsuda, Y.; Ebata, T.; Mikami, N. J. Chem. Phys. 2000, 113, 573
21. Florio, G. M.; Gruenloh, C. J.; Quimpo, R. C.; Zwier, T. S. J. Chem. Phys. 2000, 113, 11143
22. Sakota, K.; Tokuhara, S.; Sekiya, H. Chem. Phys. Lett. 2007, 448, 159
23. Hazra, M. K.; Chakraborty, T. J. Phys. Chem. A 2008, 112, 1100
24. Hazra, M. K.; Samanta, A. K.; Chakraborty, T. J. Chem. Phys. 2006, 125, 214302
25. Penfold, B. R. Acta Crystallogr. 1953, 6, 591
26. Yang, H. W.; Craven, B. M. Acta Crystallogr., Sect. B 1998, 54, 912
27. Arman, H. D.; Poplaukhin, P.; Tiekink, E. R. T. Acta Crystallogr., Sect. E 2009, 65 03187
28. Müller, A.; Talbot, F.; Leutwyler, S. J. Chem. Phys. 2000, 112, 3717
29. Müller, A.; Talbot, F.; Leutwyler, S. J. Chem. Phys. 2001, 115, 5192
30. Müller, A.; Talbot, F.; Leutwyler, S. J. Chem. Phys. 2002, 116, 2836
31. Borst, D. R.; Roscioli, J. R.; Pratt, D. W.; Florio, G. M.; Zwier, T. S.; Müller, A.; Leutwyler, S. Chem. Phys. 2002, 283, 341
32. Meuwly, M.; Müller, A.; Leutwyler, S. Phys. Chem. Chem. Phys. 2003, 5, 2663
33. Frey, J. A.; Leist, R.; Tanner, C.; Frey, H.-M.; Leutwyler, S. J. Chem. Phys. 2006, 125, 114308
34. Hammes, G. G.; Spivey, H. O. J. Am. Chem. Soc. 1966, 88, 1621
35. Hammes, G. G.; Lillford, P. J. J. Am. Chem. Soc. 1970, 92, 7578
36. Beak, P. Acc. Chem. Res. 1977, 10, 186
37. Bensaude, O.; Chevrier, M.; Dubois, J. E. J. Am. Chem. Soc. 1978, 100, 7055
38. Rawson, J. M.; Winpenny, R. E. P. Coord. Chem. Rev. 1995, 139, 313
39. Chou, P.-T.; Wei, C.-Y.; Hung, F.-T. J. Phys. Chem. B 1997, 101, 9119
40. Frank, J.; Katritzky, A. R. J. Chem. Soc., Perkin Trans. 2 1976, 1428
41. Bensaude, O.; Chevrier, M.; Dubois, J.-E. Tetrahedron Lett. 1978, 19, 2221
42. Forlani, L.; Cristoni, G.; Boga, C.; Todesco, P. E.; Del Vecchio, E.; Selva, S.; Monari, M. ARKIVOC 2002, XI, 198
43. Smets, J.; Maes, G. Chem. Phys. Lett. 1991, 187, 532
44. Nowak, M. J.; Lapinski, L.; Fulara, J.; Les, A.; Adamowicz, L. J. Phys. Chem. 1992, 96, 1562
45. Dkhissi, A.; Houben, L.; Smets, J.; Adamowicz, L.; Maes, G. J. Mol. Struct. 1999, 484, 215
46. Abdulla, H. I.; El-Bermani, M. F. Spectrochim. Acta, Part A 2001, 57, 2659
47. De Kowalewski, D. G.; Contreras, R. H.; Díez, E.; Esteban, A. Mol. Phys. 2004, 102, 2607
48. Moreno, M.; Miller, W. H. Chem. Phys. Lett. 1990, 171, 475
49. Wang, J.; Boyd, R. J. J. Phys. Chem. 1996, 100, 16141
50. Alkorta, I.; Elguero, J. J. Org. Chem. 2002, 67, 1515
51. Wolfe, S.; Weinberg, N.; Hsieh, Y. Theor. Chem. Acc. 2007, 118, 265
52. Beak, P.; Covington, J. B.; Smith, S. G. J. Am. Chem. Soc. 1976, 98, 8284
53. Coburn, R. A.; Dudek, G. O. J. Phys. Chem. 1968, 72, 1177
54. Kwiatkowski, J. S.; Leszczynski, J. J. Mol. Struct. 1996, 376, 325
55. Kwiatkowski, J. S.; Leszczyński, J. J. Mol. Struct.: THEOCHEM 1994, 312, 201
56. Müller, A.; Losada, M.; Leutwyler, S. J. Phys. Chem. A 2004, 108, 157
57. Motley, T. L.; Korter, T. M. Chem. Phys. Lett. 2008, 464, 171
58. Wójcik, M. J.; Tatara, W.; Boczar, M.; Apola, A.; Ikeda, S. J. Mol. Struct. 2001, 596, 207
59. Thanopulos, I.; Shapiro, M. J. Am. Chem. Soc. 2005, 127, 14434
60. Nibbering, E. T. J.; Elsaesser, T. Chem. Rev. 2004, 104, 1887
61. Woutersen, S.; Mu, Y.; Stock, G.; Hamm, P. Chem. Phys. 2001, 266, 137
62. Zheng, J.; Kwak, K.; Asbury, J.; Chen, X.; Piletic, I. R.; Fayer, M. D. Science 2005, 309, 1338
63. Golubev, N. S.; Smirnov, S. N.; Tolstoy, P. M.; Sharif, S.; Toney, M. D.; Denisov, G. S.; Limbach, H. H. J. Mol. Struct. 2007, 844, 319
64. Fürtig, B.; Buck, J.; Manoharan, V.; Bermel, W.; Jäschke, A.; Wenter, P.; Pitsch, S.; Schwalbe, H. Biopolymers 2007, 86, 360
65. Noble, D. L.; Aibout, A.; Horsewill, A. J. J. Magn. Reson. 2009, 201, 157
66. Lopez del Amo, J. M.; Langer, U.; Torres, V.; Pietrzak, M.; Buntkowsky, G.; Vieth, H.-M.; Shibl, M. F.; Kühn, O.; Bröring, M.; Limbach, H.-H. J. Phys. Chem. A 2009, 113, 2193
67. Noda, I. Appl. Spectrosc. 1993, 47, 1329
68. Noda, I.; Ozaki, Y. Two-Dimensional Correlation Spectroscopy; John Wiley & Sons: Chicester, 2004.
69. Noda, I. J. Mol. Struct. 2008, 883, 216
70. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; G. Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 03 (Revision C.02); Gaussian, Inc.: Pittsburgh, PA, 2003.
71. Tolstoy, P. M.; Schah-Mohammedi, P.; Smirnov, S. N.; Golubev, N. S.; Denisov, G. S.; Limbach, H.-H. J. Am. Chem. Soc. 2004, 126, 5621
72. Meschede, L.; Gerritzen, D.; Limbach, H.-H. Ber. Bunsen-Ges. Phys. Chem. Chem. Phys. 1988, 92, 469
73. Meschede, L.; Limbach, H.-H. J. Phys. Chem. 1991, 95, 10267
74. Limbach, H.-H.; Männle, F.; Detering, C.; Denisov, G. S. Chem. Phys. 2005, 319, 69
75. Nakahara, M.; C., W. Chem. Lett. 1992, 809
76. Jackson, J. E. A Users Guide to Principal Components; John Wiley & Sons: New York, 1991.
77. Rüterjans, H.; Kaun, E.; Hull, W. E.; Limbach, H.-H. Nucleic Acids Res. 1982, 10, 7027
78. Limbach, H.-H.; Pietrzak, M.; Sharif, S.; Tolstoy, P. M.; Shenderovich, I. G.; Smirnov, S. N.; Golubev, N. S.; Denisov, G. S. Chem.- Eur. J. 2004, 10, 5195
79. Motley, T. L.; Allis, D. G.; Korter, T. M. Chem. Phys. Lett. 2009, 478, 166
80. Florio, G. M.; Sibert, E. L.; Zwier, T. S. Faraday Discuss. 2001, 118, 315
81. Häber, T.; Schmitt, U.; Emmeluth, C.; Suhm, M. A. Faraday Discuss. 2001, 118, 331
82. Florio, G. M.; Zwier, T. S.; Myshakin, E. M.; Jordan, K. D.; Sibert, E. L., III J. Chem. Phys. 2003, 118, 1735
83. Emmeluth, C.; Suhm, M. A. Phys. Chem. Chem. Phys. 2003, 5, 3094
84. Emmeluth, C.; Suhm, M. A.; Luckhaus, D. J. Chem. Phys. 2003, 118, 2242
85. Antony, J.; von Helden, G.; Meijer, G.; Schmidt, B. J. Chem. Phys. 2005, 123 014305
86. Dreyer, J. J. Chem. Phys. 2005, 122, 184306
87. Dreyer, J. J. Chem. Phys. 2007, 127 054309