Quantum-chemical studies on the favored and rare tautomers of neutral and redox adenine

Journal of Physical Chemistry A

Volumn 117, Issue 7, 2013, Pages 1548-1559

  Raczyńska, Ewa D ^a   Makowski, Mariusz ^b   Zientara Rytter, Katarzyna ^a   Kolczyńska, Katarzyna ^a   Stȩpniewski, Tomasz M ^a   Hallmann, Małgorzata ^a  

^a WARSAW UNIVERSITY OF LIFE SCIENCES   (Poland)

^b UNIVERSITY OF GDA SK   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

GASES; GROUND STATE; IONIZATION POTENTIAL; MOLECULES; ORGANIC COMPOUNDS; QUANTUM CHEMISTRY; STEREOCHEMISTRY;

ADIABATIC ELECTRON AFFINITY; ADIABATIC IONIZATION POTENTIAL; AROMATIC AMINES; GASPHASE; NH GROUPS; ONE-ELECTRON OXIDATION; ONE-ELECTRON REDUCTIONS; OXIDATION AND REDUCTION; PCM MODEL; RELATIVE ENERGIES; VERTICAL DETACHMENT ENERGIES; WATER MOLECULE;

OXIDATION;

EID: 84962476503     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp3081029     Document Type: Article

References (114)

1. Saenger, W. Principles of Nucleic Acids Structures; Springer: New York, 1994.
2. Elguero, J.; Marzin, C.; Katritzky, A. R.; Linda, P. Advances in Heterocyclic Chemistry, Supplement 1; Academic Press: New York, 1976.
3. Pozharskii, A. F.; Soldatenkov, A. T.; Katritzky, A. R. Heterocycles in Life and Society; Wiley: New York, 1997.
4. Kwiatkowski, J. S.; Person, W. B. In Theoretical Biochemistry and Molecular Biology; Beveridge, D. L., Lavery, R., Eds.; Academic Press: New York, 1990; pp 153-171.
5. Raczyńska, E. D.; Kosińska, W.; Ośmiałowski, B.; Gawinecki, R. Chem. Rev. 2005, 105, 3561-3612
6. Dreyfus, M.; Dodin, G.; Bensaude, O.; Dubois, J. E. J. Am. Chem. Soc. 1975, 97, 2369-2376
7. Hirakawa, A. Y.; Okada, H.; Sasagawa, S.; Tsuboi, M. Spectrochim. Acta A 1985, 41, 209-216
8. Stepanian, S. G.; Sheina, G. G.; Radchenko, E. D.; Blagoi, Y. P. J. Mol. Struct. 1985, 131, 333-346
9. Majoube, M. J. Mol. Struct. 1986, 143, 427-430
10. Brown, R. D.; Godfrey, P. D.; Mc Naughton, D. D.; Pierlot, A. A. Chem. Phys. Lett. 1989, 156, 61-63
11. Wiorkiewicz- Kuczera, J.; Karplus, M. J. Am. Chem. Soc. 1990, 112, 5324-5340
12. Katritzky, A. R.; Karelson, M. J. Am. Chem. Soc. 1991, 113, 1561-1566
13. Czerminski, R.; Szczepaniak, K.; Person, W. B.; Kwiatkowski, J. S. J. Mol. Struct. 1990, 237, 151-163
14. Nowak, M. J.; Lapinski, L.; Kwiatkowski, J. S. Chem. Phys. Lett. 1989, 157, 14-18
15. Nowak, M. J.; Lapinski, L.; Kwiatkowski, J. S.; Leszczynski, J. Spectrochim. Acta A 1991, 47, 87-103
16. Nowak, M. J.; Rostkowska, H.; Lapinski, L.; Kwiatkowski, J. S.; Leszczynski, J. Spectrochim. Acta A 1994, 50, 1081-1094
17. Nowak, M. J.; Rostkowska, H.; Lapinski, L.; Kwiatkowski, J. S.; Leszczynski, J. J. Phys. Chem. 1994, 98, 2813-2816
18. Nowak, M. J.; Lapinski, L.; Kwiatkowski, J. S.; Leszczynski, J. J. Phys. Chem. A 1996, 100, 3527-3534
19. Majoube, M.; Millié, P.; Lagant, P.; Vergoten, G. J. Raman Spectrosc. 1994, 25, 821-836
20. Ha, T.-K.; Keller, M. J.; Gunde, R.; Gunthard, H. H. J. Mol. Struct.: THEOCHEM 1996, 364, 161-181
21. Schoone, K.; Houben, L.; Smets, J.; Adamowicz, L.; Maes, G. Spectrochim. Acta A 1996, 52, 383-396
22. Colarusso, P.; Zhang, K.; Guo, B.; Bernath, P. F. Chem. Phys. Lett. 1997, 269, 39-48
23. Holmén, A.; Broo, A. Int. J. Quant. Chem. Quant. Biol. Symp. 1995, 22, 113-122
24. Broo, A.; Holmén, A. J. Phys. Chem. A 1997, 101, 3589-3600
25. Broo, A. J. Phys. Chem. A 1998, 102, 526-531
26. Gu, J. D.; Leszczynski, J. J. Phys. Chem. A 1999, 103, 2744-2750
27. Mishra, S. K.; Shukla, M. K.; Mishra, P. C. Spectrochim. Acta A 2000, 56, 1355-1384
28. Kim, N. J.; Jeong, G.; Kim, Y. S.; Sung, J.; Kim, S. K.; Park, Y. D. J. Chem. Phys. 2000, 113, 10051-10055
29. Laxer, A.; Major, D. T.; Gottlieb, H. E.; Fischer, B. J. Org. Chem. 2001, 66, 5463-5481
30. Mennucci, B.; Toniolo, A.; Tomasi, J. J. Phys. Chem. A 2001, 105, 4749-4757
31. Plutzer, C.; Nir, E.; de Vries, M. S.; Kleinermanns, K. Phys. Chem. Chem. Phys. 2001, 3, 5466-5469
32. Plutzer, C.; Kleinermanns, K. Phys. Chem. Chem. Phys. 2002, 4, 4877-4882
33. Salter, L. M.; Chaban, G. M. J. Phys. Chem. A 2002, 106, 4251-4256
34. Sukhanov, O. S.; Shishkin, O. V.; Grob, L.; Podolyan, Y.; Leszczynski, J. J. Phys. Chem. B 2003, 107, 2846-2852
35. Hanus, M.; Kabelac, M.; Rejnek, J.; Ryjacek, F.; Hobza, P. J. Phys. Chem. B 2004, 108, 2087-2097
36. Wang, F.; Downton, M. T.; Kidwani, N. J. Theoret. Comput. Chem. 2005, 4, 247-264
37. Saha, S.; Wang, F.; Brunger, M. J. Mol. Simul. 2006, 32, 1261-1270
38. Downton, M. T.; Wang, F. Mol. Simul. 2006, 32, 667-672
39. Guerra, C. F.; Bickelhaupt, F. M.; Saha, S.; Wang, F. J. Phys. Chem. A 2006, 110, 4012-4020
40. Close, D. M.; Crespo-Hernandez, C. E.; Grob, L.; Leszczynski, J. J. Phys. Chem. A 2008, 112, 12702-12706
41. Dybiec, K.; Molchanov, S.; Gryff-Keller, A. Pol. J. Chem. 2009, 83, 857-868
42. Mohamed, T. A.; Shabaan, I. A.; Zoghaib, W. M.; Husband, J.; Farag, R. S.; Alajhaz, A. E. M. A. J. Mol. Struct. 2009, 938, 263-276
43. Polewskii, K.; Zinger, D.; Trunk, J.; Sutherland, J. C. Radiat. Phys. Chem. 2011, 80, 1092-1098
44. Zierkiewicz, W.; Komorowski, L.; Michalska, D.; Cerny, J.; Hobza, P. J. Phys. Chem. B 2008, 112, 16734-16740
45. Cyrański, M. K.; Gilski, M.; Jaskólski, M.; Krygowski, T. M. J. Org. Chem. 2003, 68, 8607-8613
46. Cysewski, P. J. Mol. Struct.: THEOCHEM 2005, 714, 29-34
47. Huertas, O.; Poater, J.; Fuentes-Cabrera, M.; Orozco, M.; Sola, M.; Luque, F. J. J. Phys. Chem A 2006, 110, 12249-12258
48. Sun, G. Y.; Nicklaus, M. C. Theor. Chem. Acc. 2007, 117, 323-332
49. Vogt, N.; Dorofeeva, O. V.; Sipachev, V. A.; Rykov, A. N. J. Phys. Chem. A 2009, 113, 13816-13823
50. Malikova, K.; Novosadova, L.; Pipiska, M.; Marek, R. Chem. Phys. Chem. 2011, 12, 379-388
51. Haranczyk, M.; Gutowski, M.; Li, X.; Bowen, K. H. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 4804-4807
52. Raczyńska, E. D.; Kolczyńska, K.; Stȩpniewski, T. M. J. Mol. Model. 2012, 18, 3523-3533
53. Raczyńska, E. D. Comput. Theoret. Chem. 2012, 993, 73-79
54. Raczyńska, E. D.; Kamińska, B. J. Phys. Org. Chem. 2010, 23, 823-835
55. Watson, J. D.; Crick, F. H. C. Nature 1953, 171, 964-967
56. Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecular Orbital Theory; Oxford University Press: New York, 1989.
57. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
58. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
59. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab initio Molecular Theory; Wiley: New York, 1986.
60. Miertus, S.; Tomasi, J. Chem. Phys. 1982, 65, 239-241
61. Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117-129
62. Frisch, M. J.; Gaussian 03; Gaussian, Inc.: Wallingford, CT, 2004, (a) Revision E.01, (b) Revision D.02.
63. Rodríguez-Santiago, L.; Vendrell, O.; Tejero, I.; Sodupe, M.; Bertran, J. Chem. Phys. Lett. 2001, 334, 112-118
64. Exner, O.; Bohm, S. Collect. Czech. Chem. Commun. 2006, 71, 1239-1255
65. Lipping, L.; Kutt, A.; Kaupmess, K.; Koppel, I.; Burk, P.; Leito, I.; Koppel, I. A. J. Phys. Chem. A 2011, 115, 10335-10344
66. Gutowski, M.; Da̧bkowska, I.; Rak, J.; Xu, S.; Nilles, J. M.; Radisic, D.; Bowen, K. H., Jr. Eur. Phys. J. D 2002, 20, 431-439
67. Fogarasi, G. J. Mol. Struct. 2010, 978, 257-262
68. Lammertsma, K.; Prasad, B. V. J. Am. Chem. Soc. 1994, 116, 642-650
69. Raczyńska, E. D.; Stȩpniewski, T. M.; Kolczyńska, K. J. Mol. Model. 2011, 17, 3229-3239
70. Alkorta, I.; Elguero, J.; Liebman, J. F. Struct. Chem. 2006, 17, 439-444
71. Riestra-Kiracofe, J. C.; Tschumper, G. S.; Schaefer, H. F., III; Nandi, S.; Ellison, G. B. Chem. Rev. 2002, 102, 231-282
72. Close, D. M. J. Phys. Chem. A 2004, 108, 10376-10379
73. Lin, X. J.; Wang, Q.; Wu, J.; Liu, C. B. J. Theoret. Comput. Chem. 2008, 7, 457-472
74. Shukla, M. K.; Leszczynski, J. Mol. Phys. 2010, 108, 3131-3146
75. Shanmugasundaram, M.; Puranik, M. Phys. Chem. Chem. Phys. 2011, 13, 3851-3862
76. Li, G. S.; Ruiz-López, M. F.; Zhang, M.-S.; Maigret, B. J. Mol. Struct.: THEOCHEM 1998, 422, 197-204
77. Lias, S. G. In NIST Chemistry WebBook, NIST Standard Reference Database Number 69; Linstrom, P. J.,; Mallard, W. G., Eds.; National Institute of Standards and Technology: Gaithersburg, MD, htpp://webbook.nist.gov.
78. Bartmess, J. E. In NIST Chemistry WebBook, NIST Standard Reference Database Number 69; Linstrom, P. J.,; Mallard, W. G., Eds.; National Institute of Standards and Technology: Gaithersburg, MD, htpp://webbook.nist.gov.
79. Singh, R. K.; Oritz, J. V.; Mishra, M. K. Int. J. Quantum Chem. 2010, 110, 1901-1915
80. Verkin, B. I.; Sukodub, L. F.; Yanson, I. K. Dokl. Akad. Nauk. SSSR 1976, 228, 1452-1455
81. Lifschitz, C.; Bergmann, E. D.; Pullman, B. Tetrahedron Lett. 1967, 4583-4586
82. Hwang, C. T.; Stumpf, C. L.; Yu, Y.-Q.; Kenttämaa, H. I. Int. J. Mass. Spectrom. 1999, 182/183, 253-259
83. Hush, N. S.; Cheung, A. S. Chem. Phys. Lett. 1975, 34, 11-13
84. Peng, S.; Padva, A.; LeBreton, P. R. Proc. Natl. Acad. Sci. U.S.A. 1976, 73, 2966-2968
85. Lin, J.; Yu, C.; Peng, S.; Akiyama, I.; Li, K.; Lee, L. K.; LeBreton, P. R. J. Am. Chem. Soc. 1980, 102, 4627-4631
86. Russo, N.; Toscano, M.; Grand, A. J. Comput. Chem. 2000, 21, 1243-1250
87. Wetmore, S. D.; Boyd, R. J.; Erikson, L. A. Chem. Phys. Lett. 2000, 322, 129-135
88. Li, X.; Bowen, K. H.; Haranczyk, M.; Bachorz, R. A.; Mazurkiewicz, K.; Rak, J.; Gutowski, M. J. Chem. Phys. 2007, 127, 174309
89. Desfrancois, C.; Abdoul-Carime, H.; Schremann, J. P. J. Chem. Phys. 1996, 104, 7792-7794
90. Aflatooni, K.; Gallup, G. A.; Burrow, P. D. J. Phys. Chem. 1998, 102, 6205-6207
91. Wiley, J. R.; Robinson, J. M.; Ehdaie, S.; Chen, E. C. M.; Chen, E. S. D; Wentworth, W. E. Biochem. Biophys. Res. Commun. 1991, 180, 841-845
92. Chen, E. S. D.; Chen, E. C. M.; Sane, N.; Shulze, S. Bioelectrochem. Bioenerg. 1999, 48, 69-78
93. Raczyńska, E. D.; Makowski, M.; Szela̧g, M.; Kamińska, B.; Zientara, K. J. Mol. Struct.: THEOCHEM 2010, 947, 83-91
94. Ramazzina, I.; Folli, C.; Secchi, A.; Berni, R.; Percudani, R. Nat. Chem. Biol. 2006, 2, 144-148 and references cited therein.
95. Colloc'h, N.; El Hajji, M.; Bachet, B.; L'Hermete, G.; Schiltz, M.; Prangé, T.; Castro, B.; Mornon, J.-P. Nat. Struct. Biol. 1997, 4, 947-952
96. Retailleau, P.; Colloc'h, N.; Vivares, D.; Bonneté, F.; Castro, B.; El Hajji, M.; Mornon, J.-P.; Monard, G.; Prangé, T. Acta Cryst. D 2004, 60, 453-462
97. Retailleu, P.; Colloc'h, N.; Vivares, D.; Bonneté, F.; Castro, B.; El Hajji, M.; Prangé, T. Acta Cryst. D 2004, 61, 218-229
98. Müller-Dethlefs, K.; Hobza, P. Chem. Rev. 2000, 100, 143-168
99. Kryachenko, E. S. Int. Quantum Chem. 2002, 90, 910-923
100. Grebneva, H. A. J. Mol. Struct. 2003, 645, 133-143
101. Danilov, V. I.; Anisimov, V. M.; Kurita, N.; Hovorun, D. Chem. Phys. Lett. 2005, 412, 285-293
102. Wood, R. D.; Mitchell, M.; Sgouros, J.; Lindahl, T. Science 2001, 291, 1284-1289
103. Pena-Diaz, J.; Jiricny, J. Trends Biochem. Sci. 2012, 37, 206-214
104. Cuthbert, A. W. Br. J. Pharmacol. 2011, 163, 173-183
105. Buery, R. R.; Siar, C. H.; Katase, N.; Gunduz, M.; Lefeuvre, M.; Fujii, M.; Inoue, M.; Setsu, K.; Nagatsuka, H. Oncol. Rep. 2011, 26, 783-787
106. Macedo, M. P.; Andrade Lde, B.; Coudry, R.; Crespo, R.; Gomes, M.; Lisboa, B. C.; Aguiar, S., Jr.; Soares, F. A.; Carraro, D. M.; Cunha, I. W. Int. J. Colorectal Dis. 2011, 26, 1241-1248
107. Okudela, K.; Woo, T.; Kitamura, H. Pathol. Int. 2010, 60, 651-660
108. Delpu, Y.; Hanoun, N.; Lulka, H.; Sicard, F.; Selves, J.; Buscail, L.; Torrisani, J.; Cordelier, P. Curr. Genomics 2011, 12, 15-24
109. Li, X. F.; Cai, Z. L.; Sevilla, M. D. J. Phys. Chem. A 2002, 106, 1596-1603
110. Mc Laferty, F. W.; Tureček, F. Interpretation of Mass Spectra; University Science Books: Mill Valley, 1993.
111. Johnstone, R. A. W.; Rose, M. E. Mass Spectrometry for Chemists and Biochemists; Cambridge University Press: London, 1996.
112. Michael, B. R.; O'Neill, P. Science 2000, 287, 1603-1604
113. Sanche, L. Mass Spectrom. Rev. 2002, 21, 349-369
114. Tureček, F. Eur.J. Mass Spectrom. 2007, 52, 89-120