Distonic isomers and tautomers of the adenine cation radical in the gas phase and aqueous solution

Journal of Physical Chemistry A

Volumn 108, Issue 42, 2004, Pages 9283-9293

  Chen, Xiaohong ^a   Syrstad, Erik A ^a   Nguyen, Minh Tho ^b   Gerbaux, Pascal ^c   Tureček, František ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

^b UNIVERSITY OF LEUVEN   (Belgium)

^c UNIVERSITY OF MONS   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ADENINE; GAS PHASE; PROTON AFFINITY; TAUTOMERS;

AMINO ACIDS; DISSOCIATION; HYDROGEN; METHANOL; NUCLEAR MAGNETIC RESONANCE; POSITIVE IONS; SOLUTIONS; SPECTRUM ANALYSIS;

ISOMERS;

EID: 7644244133     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp046575q     Document Type: Article

References (92)

1. (a) Hammerum, S. Mass Spectrom. Rev. 1988, 7, 123-202.
2. (b) Stirk, K. M.; Kiminkinen, L. K. M.; Kenttamaa, H. I. Chem. Rev. 1992, 92, 1649-1665.
3. (a) Tureček, F.; Smutek, M.; Hanuš, V. Org. Mass Spectrom. 1981, 16, 483-489. For a. comprehensive review, see
4. (b) Grützmacher, H.-F. Int. J. Mass Spectrom. Ion Processes 1992, 118/119, 825-855.
5. Yates, B. F.; Bouma, W.; Radom, L. J. Am. Chem. Soc. 1984, 106, 5805-5808.
6. Yates, B. F.; Bouma, W.; Radom, L. J. Am. Chem. Soc. 1987, 109, 2250-2263.
7. (a) Flammang, R.; Barbieux-Flammang, M.; Gualano, E.; Gerbaux, P.; Le, H. T.; Ngnyen, M. T.; Tureček, F.; Vivekananda, S. J. Phys. Chem. A 2001, 105, 8579-8587.
8. (b) Flammang, R.; Flammang-Barbieux, M.; Gualano, E.; Gerbaux, P.; Le, H. T.; Nguyen, M. T.; Tureček, F. Int. J. Mass Spectrom. 2002, 217, 65-73.
9. (a) Lavorato, D. J.; Terlouw, J. K.; Dargel, T. K.; Koch, W.; McGibbon, G. A.; Schwarz, H. J. Am. Chem. Soc. 1996, 118, 11898-11904.
10. (b) Lavorato, D. J.; Terlouw, J. K.; McGibbon, G. A.; Dargel, T. K.; Koch, W.; Schwarz, H. Int. J. Mass Spectrom. 1998, 179/180, 7-14.
11. Lavorato, D. J.; Fell, L. M.; McGibbon, G. A.; Sen, S.; Terlouw, J. K.; Schwarz, H. Int. J. Mass Spectrom. 2000, 195/196, 71-83.
12. Lavorato, D. J.; Dargel, T. K.; Koch, W.; McGibbon, G. A.; Schwarz, H.; Terlouw, J. K. Int. J. Mass Spectrom. 2001, 210/211, 43-57.
13. Dargel, T. K.; Koch, W.; Lavorato, D. J.; McGibbon, G. A.; Terlouw, J. K.; Schwarz, H. Int. J. Mass Spectrom. 1999, 185/186/187, 925-933.
14. McGibbon, G. A.; Heinemann, C.; Lavorato, D. J.; Schwarz, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1478-1481.
15. McGibbon, G. A.; Hrusak, J.; Lavorato, D. J.; Schwarz, H.; Terlouw, J. K. Chem. - Eur. J. 1997, 3, 232-236.
16. Karni, A.; Mandelbaum, A. Org. Mass Spectrom. 1980, 15, 53-
17. McLafferty, F. W.; Tureček, F. Interpretation of Mass Spectra, 4th ed.; University Science Books: Sausalito, CA, 1993; pp 55, 176.
18. Šponar, J.; Hobza, P. Collect. Czech. Chem. Commun. 2003, 68, 2231-2282.
19. Improta, R.; Scalmani, G.; Barone, V. Int. J. Mass Spectrom. 2000, 201, 321-336.
20. Li, X.; Cai, Z.; Sevilla, M. D. J. Phys. Chem. A 2002, 106, 9345-9351.
21. (a) Steenken, S.; Jovanovic, S. V. J. Am. Chem. Soc. 1997, 119, 617-618.
22. (b) Steenken, S. Biol. Chem. 1997, 378, 1293-1297.
23. Steenken, S. Chem. Rev. 1989, 89, 503-520.
24. Steenken, S. Free Radical Res. Commun. 1992, 16, 349-379.
25. (a) Crespo-Hernandez, C. E.; Martinez, L.; Gonzalez-Sierra, A. E.; Robles-Irizarry, L.; Diaz-Vazquez, A.; Arce, R. J. Photochem. Photobiol., A 2002, 152, 123-133.
26. (b) Reynisson, J.; Steenken, S. Phys. Chem. Chem. Phys. 2002, 4, 527-532.
27. Sartor, V.; Boone, E.; Schuster, G. B. J. Phys. Chem. B 2001, 105, 11057-11059.
28. Bertran, J.; Oliva, A.; Rodriguez-Santiago, L.; Sodupe, M. J. Am. Chem. Soc. 1998, 120, 8159-8167.
29. (e) Hutte, M.; Clark, T. J. Am. Chem. Soc. 1996, 118, 7574-7577.
30. (f) Faraggi, M.; Ferradini, C.; Jay-Gerin, J.-P. New J. Chem. 1995, 19, 1203-1215.
31. (g) Al-Sheikhly, M. Radiat. Phys. Chem. 1994, 44, 297-301.
32. (h) Nelson, W. H.; Sagstuen, E.; Hole, E. O.; Close, D. M. Radiat. Res. 1992, 131, 272-284.
33. Yan, M.; Becker, D.; Summerfeld, S.; Renke, P.; Sevilla, M. D. J. Phys. Chem. 1992, 96, 1983-1989.
34. (j) Candeias, L. P.; O'Neffl, P.; Jones, G. D. D.; Steenken, S. Int. J. Radiat. Biol. 1992, 61, 15-20.
35. (k) Sevilla, M. D.; Becker, D.; Yan, M.; Summerfield, S. R. J. Phys. Chem. 1991, 95, 3409-3415.
36. Sevilla, M. D.; Mohan, P. A. Int. J. Radiat. Biol. 1974, 25, 635-638.
37. Nelson, W. H.; Sagstuen, E.; Hole, E. O.; Close, D. M. Radiat. Res. 1992, 131, 272-284.
38. Laxer, A.; Major, D. T.; Gottlieb, H. E.; Fischer, B. J. Org. Chem. 2001, 66, 5463-5481.
39. Bateman, R. H.; Brown, J.; Lefevere, M.; Flammang, R.; Van Haverbeke, Y. Int. J. Mass Spectrom. Ion Processes 1992, 115, 205-218.
40. (a) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; 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.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.6; Gaussian, Inc.: Pittsburgh, PA, 1998.
41. (b) 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.; 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, revision B.05; Gaussian, Inc.: Pittsburgh, PA, 2003.
42. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 1372-1377.
43. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
44. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627.
45. (a) Schlegel, H. B. J. Chem. Phys. 1986, 84, 4530-4534.
46. (b) Mayer, I. Adv. Quantum Chem. 1980, 12, 189-262.
47. Tureček, F. J. Phys. Chem. A 1998, 102, 4703-4713.
48. (a) Rablen, P. R.; Bentrup, K. H. J. Am. Chem. Soc. 2003, 125, 2142-2147.
49. (b) Rablen, P. R. J. Org. Chem. 2000, 65, 7930-7937.
50. Rablen, P. R. J. Am. Chem. Soc. 2000, 122, 357-368.
51. (a) Tureček, F.; Wolken, J. K. J. Phys. Chem. A 1999, 103, 1905-1912.
52. (b) Wolken, J. K.; Tureček, F. J. Am. Chem. Soc. 1999, 121, 6010-6018.
53. Wolken, J. K.; Tureček, F. J. Phys. Chem. A 1999, 103, 6268-6281.
54. Tureček, F.; Carpenter, F. H.; Polce, M. J.; Wesdemiotis, C. J. Am. Chem. Soc. 1999, 121, 7955-7956.
55. (e) Tureček, F.; Polášek, M.; Frank, A. J.; Sadílek. M. J. Am. Chem. Soc. 2000, 122, 2361-2370.
56. Polášek, M.; Tureček, F. J. Am. Chem. Soc. 2000, 122, 9511-9524.
57. Čížek, J.; Paldus, J.; Šroubková, L. Int. J. Quantum Chem. 1969, 3, 149-167.
58. Purvis, G. D.; Bartlett, R. J. J. Chem. Phys. 1982, 76, 1910-1918.
59. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735-746.
60. (a) Hegarty, D.; Robb, M. A. Mol. Phys. 1979, 38, 1795-1812.
61. (b) Frisch, M.; Ragazos, I. N.; Robb, M. A.; Schlegel, H. B. Chem. Phys. Lett. 1992, 189, 524-528.
62. (a) Barone, V.; Cossi, M.; Tomasi, J. J. Chem. Phys. 1997, 107, 3210-3221.
63. (b) Cossi, M.; Scalmani, G.; Rega, N.; Barone, V. J. Chem. Phys. 2002, 117, 43-54.
64. Major, D. T.; Laxer, A.; Fischer, B. J. Org. Chem. 2002, 67, 790-802.
65. For recent studies of protonation sites in heterocycles and nucleo-bases, see (a) Wolken, J. K.; Syrstad, E. A.; Vivekananda, S.; Tureček, F. J. Am. Chem. Soc. 2001, 123, 5804-5805. (b) Wolken, J. K.; Tureček, F. J. Phys. Chem. A 2001, 105, 8352-8360. Wolken, J. K.; Tureček, F. J. Am. Soc. Mass Spectrom. 2000 11, 1065-1071. Wolken, J. K.; Tureček, F. J. Am. Chem. Soc. 1999, 121, 6010-6018. (e) Nguyen, V. Q.; Tureček, F. J. Am. Chem. Soc. 1997, 119, 2280-2290. (f) Nguyen, V. Q.; Tureček, F. J. Mass Spectrom. 1997, 32, 55-63. (g) Nguyen, V. Q.; Tureček, F. J. Mass Spectrom. 1996, 31, 1173-1184.
66. For recent studies of protonation sites in heterocycles and nucleo-bases, see (a) Wolken, J. K.; Syrstad, E. A.; Vivekananda, S.; Tureček, F. J. Am. Chem. Soc. 2001, 123, 5804-5805. (b) Wolken, J. K.; Tureček, F. J. Phys. Chem. A 2001, 105, 8352-8360. Wolken, J. K.; Tureček, F. J. Am. Soc. Mass Spectrom. 2000 11, 1065-1071. Wolken, J. K.; Tureček, F. J. Am. Chem. Soc. 1999, 121, 6010-6018. (e) Nguyen, V. Q.; Tureček, F. J. Am. Chem. Soc. 1997, 119, 2280-2290. (f) Nguyen, V. Q.; Tureček, F. J. Mass Spectrom. 1997, 32, 55-63. (g) Nguyen, V. Q.; Tureček, F. J. Mass Spectrom. 1996, 31, 1173-1184.
67. For recent studies of protonation sites in heterocycles and nucleo-bases, see (a) Wolken, J. K.; Syrstad, E. A.; Vivekananda, S.; Tureček, F. J. Am. Chem. Soc. 2001, 123, 5804-5805. (b) Wolken, J. K.; Tureček, F. J. Phys. Chem. A 2001, 105, 8352-8360. Wolken, J. K.; Tureček, F. J. Am. Soc. Mass Spectrom. 2000 11, 1065-1071. Wolken, J. K.; Tureček, F. J. Am. Chem. Soc. 1999, 121, 6010-6018. (e) Nguyen, V. Q.; Tureček, F. J. Am. Chem. Soc. 1997, 119, 2280-2290. (f) Nguyen, V. Q.; Tureček, F. J. Mass Spectrom. 1997, 32, 55-63. (g) Nguyen, V. Q.; Tureček, F. J. Mass Spectrom. 1996, 31, 1173-1184.
68. For recent studies of protonation sites in heterocycles and nucleo-bases, see (a) Wolken, J. K.; Syrstad, E. A.; Vivekananda, S.; Tureček, F. J. Am. Chem. Soc. 2001, 123, 5804-5805. (b) Wolken, J. K.; Tureček, F. J. Phys. Chem. A 2001, 105, 8352-8360. Wolken, J. K.; Tureček, F. J. Am. Soc. Mass Spectrom. 2000 11, 1065-1071. Wolken, J. K.; Tureček, F. J. Am. Chem. Soc. 1999, 121, 6010-6018. (e) Nguyen, V. Q.; Tureček, F. J. Am. Chem. Soc. 1997, 119, 2280-2290. (f) Nguyen, V. Q.; Tureček, F. J. Mass Spectrom. 1997, 32, 55-63. (g) Nguyen, V. Q.; Tureček, F. J. Mass Spectrom. 1996, 31, 1173-1184.
69. For recent studies of protonation sites in heterocycles and nucleo-bases, see (a) Wolken, J. K.; Syrstad, E. A.; Vivekananda, S.; Tureček, F. J. Am. Chem. Soc. 2001, 123, 5804-5805. (b) Wolken, J. K.; Tureček, F. J. Phys. Chem. A 2001, 105, 8352-8360. Wolken, J. K.; Tureček, F. J. Am. Soc. Mass Spectrom. 2000 11, 1065-1071. Wolken, J. K.; Tureček, F. J. Am. Chem. Soc. 1999, 121, 6010-6018. (e) Nguyen, V. Q.; Tureček, F. J. Am. Chem. Soc. 1997, 119, 2280-2290. (f) Nguyen, V. Q.; Tureček, F. J. Mass Spectrom. 1997, 32, 55-63. (g) Nguyen, V. Q.; Tureček, F. J. Mass Spectrom. 1996, 31, 1173-1184.
70. For recent studies of protonation sites in heterocycles and nucleo-bases, see (a) Wolken, J. K.; Syrstad, E. A.; Vivekananda, S.; Tureček, F. J. Am. Chem. Soc. 2001, 123, 5804-5805. (b) Wolken, J. K.; Tureček, F. J. Phys. Chem. A 2001, 105, 8352-8360. Wolken, J. K.; Tureček, F. J. Am. Soc. Mass Spectrom. 2000 11, 1065-1071. Wolken, J. K.; Tureček, F. J. Am. Chem. Soc. 1999, 121, 6010-6018. (e) Nguyen, V. Q.; Tureček, F. J. Am. Chem. Soc. 1997, 119, 2280-2290. (f) Nguyen, V. Q.; Tureček, F. J. Mass Spectrom. 1997, 32, 55-63. (g) Nguyen, V. Q.; Tureček, F. J. Mass Spectrom. 1996, 31, 1173-1184.
71. For recent studies of protonation sites in heterocycles and nucleo-bases, see (a) Wolken, J. K.; Syrstad, E. A.; Vivekananda, S.; Tureček, F. J. Am. Chem. Soc. 2001, 123, 5804-5805. (b) Wolken, J. K.; Tureček, F. J. Phys. Chem. A 2001, 105, 8352-8360. Wolken, J. K.; Tureček, F. J. Am. Soc. Mass Spectrom. 2000 11, 1065-1071. Wolken, J. K.; Tureček, F. J. Am. Chem. Soc. 1999, 121, 6010-6018. (e) Nguyen, V. Q.; Tureček, F. J. Am. Chem. Soc. 1997, 119, 2280-2290. (f) Nguyen, V. Q.; Tureček, F. J. Mass Spectrom. 1997, 32, 55-63. (g) Nguyen, V. Q.; Tureček, F. J. Mass Spectrom. 1996, 31, 1173-1184.
72. Hunter, E. P.; Lias, S. G. J. Phys. Chem. Ref. Data 1998, 27, 413.
73. Podolyan, Y.; Gorb, L.; Leszczynski, J. J. Phys. Chem. A 2000, 104, 7346-7352.
74. Harrison, A. G. Chemical Ionization Mass Spectrometry, 2nd ed.; CRC Press: Boca Raton, FL, 1992; p 30.
75. (a) Wolken, J. K.; Syrstad, E. A.; Vivekananda, S.; Tureček, F. J. Am. Chem. Soc. 2001, 123, 5804-5805.
76. (b) Syrstad, E. A.; Vivekananda, S.; Tureček, F. J. Phys. Chem. A 2001, 105, 8339-8351.
77. Seymour, J. L.; Syrstad, E. A.; Langley, C. C.; Tureček, F. Int. J. Mass Spectrom. 2003, 228, 687-702.
78. (a) Thoelmann, D.; Gruetzmacher, H.-F. J. Am. Chem. Soc. 1991, 113, 3281-3287.
79. (b) Nixdorf, A.; Grutzmacher, H.-F. J. Am. Chem. Soc. 1997, 119, 6544-6551.
80. Hanus, M.; Kabeláč, M.; Rejnek, J.; Ryjáček, F.; Hobza, P. J. Phys. Chem. B 2004, 108, 2087-2097.
81. Orlov, V. M.; Smirnov, A. N.; Varshavsky, Y. M. Tetrahedron Lett. 1976, 48, 4377-4378.
82. Hush, N. S.; Cheung, A. S. Chem. Phys. Lett. 1975, 34, 11-13.
83. Lin, J.; Yu, C.; Peng, S.; Akiyama, I.; Li, K.; Lee, L. K.; LeBreton, P. R. J. Am. Chem. Soc. 1980, 102, 4627-4631.
84. Hwang, C. T.; Stumpf, C. L.; Yu, Y.-Q.; Kenttamaa, H. I. Int. J. Mass Spectrom. 1999, 182/183, 253-259.
85. adiab = 8.25 eV in excellent agreement with both the photoionization and B3-PMP2-calculated values.
86. Gerbaux, P. Unpublished results.
87. Armentrout, P. B.; Simons, J. J. Am. Chem. Soc. 1992, 114, 8627-8633.
88. Tureček, F.; Yao, C. J. Phys. Chem. A 2003, 107, 9221-9231.
89. Christensen, J. J.; Rytting, J. H.; Izatt, R. M. Biochemistry 1970, 9, 4907-4913.
90. Tureček, F.; Wolken, J. K. J. Phys. Chem. A 2001, 105, 8740-8747.
91. Rauk, A.; Yu, D.; Armstrong, D. A. J. Am. Chem. Soc. 1998, 120, 8848-8855.
92. Rauk, A.; Yu, D.; Taylor, J.; Shustov, G. V.; Block. D. A.; Armstrong, D. A. Biochemistry 1999, 38, 9089-9096.