Origin of reverse stability of diphosphouracil tautomers compared to their analogue uracil: DFT and ab initio study

Journal of Molecular Structure: THEOCHEM

Volumn 851, Issue 1-3, 2008, Pages 54-62

  El Gogary, Tarek M ^a   El Nahas, Ahmed M ^b  

^a JAZAN UNIVERSITY   (Saudi Arabia)

^b Menoufia University   (Egypt)

Author keywords

BMK; CBS QB3; Diphosphouracil; Rotamers; Tautomerization; Uracil

Indexed keywords

EID: 84962449248     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2007.10.043     Document Type: Article

References (74)

1. March J. Advanced Organic Chemistry, Reaction, Mechanism and Structure. 4th ed. (1993), John Wiley, New York
2. Saenger W. Principles of Nucleic Acid Structure (1994), Springer, New York
3. Shimanouchi T., Tsuboi M., and Kyogoku Y. Adv. Chem. Phys. 7 (1964) 435
4. Lord R.C., and Thomas G.J. Spectrochim. Acta A 23 (1967) 2551
5. Lauer G., Schafer A., and Schweig A. Tetrahedron Lett. 45 (1975) 3939
6. Dougherty D., Wittel K., Meeks J., and McGlynn S.P. J. Am. Chem. Soc. 98 (1976) 3815
7. Padva A., O'Donnell T.J., and LeBreton P.R. Chem. Phys. Lett. 41 (1976) 278
8. Fujii M., Tamura T., Mikami N., and Ito M. Chem. Phys. Lett. 126 (1986) 583
9. Tsuchiya Y., Fujii M., and Ito M. J. Phys. Chem. 92 (1988) 1760
10. Brady B.B., Peteanu L.A., and Leavy D.H. Chem. Phys. Lett. 147 (1988) 538
11. Kubota M., and Kobayashi T. J. Electron Spectrosc. Relat. Phenom. 82 (1996) 61
12. Shugar D., and Szczepaniak K. Int. J. Quantum Chem. 20 (1981) 573
13. Szczesniak M., Nowak M.J., Szczepaniak K., Person W.B., and Shugar D. J. Am. Chem. Soc. 105 (1983) 5969
14. Chin S., Scot I., Szczepaniak K., and Person W.B. J. Am. Chem. Soc. 106 (1984) 3415
15. Radchenko Y.D., Scheina G.G., Smorygo N.A., and Blagoi Y.P. J. Mol. Struct. (THEOCHEM) 116 (1984) 387
16. Brown R.D., Godfrey P.D., McNaughton D., and Pierlot A.P. J. Am. Chem. Soc. 110 (1988) 2329
17. Kulakowska I., Geller M., Lesyng B., Wierzchowski K.L., and Bolewska K. Biochim. Biophys. Acta 407 (1975) 420
18. Brady B.B., Peteanu L.A., and Levy D.H. Chem. Phys. Lett. 147 (1981) 538
19. Beak P., and White J.M. J. Am. Chem. Soc. 104 (1982) 7073
20. Kwiatkowski J.S., Bartlett R.J., and Person W.B. J. Am. Chem. Soc. 110 (1988) 2353
21. Basch H., Garmer D.R., Jasien P.G., Krauss M., and Stevens W. J. Chem. Phys. 163 (1989) 514
22. Leś A., and Adamowicz L. J. Phys. Chem. 93 (1989) 1649
23. Gould I.R., and Hillier I.H. J. Chem. Soc., Perkin Trans. 2 2 (1990) 329
24. Leś A., and Adamowicz L. J. Phys. Chem. 94 (1990) 7021
25. Jasien P.G., and Fitzgerald G. J. Chem. Phys. 93 (1990) 2554
26. Leszczynski J. Int. J. Quantum Chem. Quant. Biol. Symp. 18 (1991) 9
27. Katritzky A.R., and Karelson M. J. Chem. Soc. Perkin Trans. 2 3 (1991) 1561
28. Leszczynski J. J. Phys. Chem. 96 (1992) 1649
29. Estrin D.A., Paglieri L., and Corongiu G. J. Phys. Chem. 98 (1994) 5653
30. Gould I.R., Burton N.A., Hall R.J., and Hillier I.H. J. Mol. Struct. (THEOCHEM) 331 (1995) 147
31. Paglieri L., Corongiu G., and Estrin D.A. Int. J. Quantum Chem. 56 (1995) 615
32. Monshi M., Al-Farhan K., Al-Resayes S., Ghaith A., and Hasanein A.A. Spectrochim. Acta A 53 (1997) 2669
33. Tian S.X., Zhang C.F., Zhang Z.J., Chen X.J., and Xu K.Z. Chem. Phys. 242 (1999) 217
34. Kawaharaa S.I., Uchimarua T., and Sekineb M. J. Mol. Struct. (Theochem) 530 (2000) 109
35. Shukla M.K., and Leszczynski J. J. Phys. Chem. A 106 (2002) 8642
36. Li X., Sanche L., and Sevilla M.D. J. Phys. Chem. A 106 (2002) 11248
37. Laudo M.D., Whittleton S.R., and Wetmore S.D. J. Phys. Chem. A 107 (2003) 10406
38. Piacenza M., and Grimme S. J. Comput. Chem. 25 (2004) 83
39. Dabkowska I., Rak J., Gutowskia M., Michael Nilles J., Stokes S.T., and Bowen K.H. J. Chem. Phys. 120 (2004) 1
40. Hu X., Li H., Liang W., and Han S. J. Phys. Chem. B 108 (2004) 12999
41. Zhang R., Ceulemans A., and Nguyen M.T. Mol. Phys. 103 (2005) 983
42. Hu X., Li H., Liang W., and Han S. J. Phys. Chem. B 109 (2005) 5935
43. Wolken J.K., and Turecek F. J. Am. Soc. Mass Spectrom. 11 (2000) 1065
44. Esposito V., Randazzo A., Piccialli G., Petraccone L., Giancola C., and Mayol L. Org. Biomol. Chem. 2 (2004) 313
45. Wetmore S.D., Boyd R.J., and Eriksson L.A. Chem. Phys. Lett. 343 (2001) 151
46. Civcir P.U. J. Phys. Org. Chem. 14 (2001) 171
47. Denifl S., Matejcik S., Gstir B., Hanel G., Probst M., Scheier P., and Maerka T.D. J. Chem. Phys. 118 (2003) 4107
48. Saenger W., and Suck D. Eur. J. Biochem. 82 (1973) 473
49. Lezius A.G., and Scheit K.H. Eur. J. Biochem. 3 (1967) 85
50. Scheit K.H., and Gartner E. Biochim. Biophys. Acta 182 (1969) 10
51. Gottschalk E., Kopp E., and Lezius A.G. Eur. J. Biochem. 24 (1971) 168
52. Jalbout A.F., Trzaskowski B., Xia Y., Li Y., Hu X., Li H., El-Nahas A.M., and Adamowicz L. Chem. Phys. 332 (2007) 152
53. M.J. Frisch, et al., Gaussian 03, revision C.02, Gaussian, Inc., Pittsburgh Wallingford, CT, 2004.
54. Becke A.D. J. Chem. Phys. 98 (1993) 5648
55. Lee C., Yang W., and Parr R.G. Phys. Rev. B 37 (1988) 785
56. Stephens P.J., Devlin F.J., Chabalowski C.F., and Frisch M.J. Phys. Chem. 98 (1994) 11623
57. Lynch B.J., Fast P.L., Harris M., and Truhlar D.G. J. Phys. Chem. A 104 (2000) 4811
58. Perdew J.P., Chevary J.A., Vosko S.H., Jackson K.A., Pederson M.R., Singh D.J., and Fiolhais C. Phys. Rev. B 46 (1992) 6671
59. Adamo C., and Barone V. J. Chem. Phys. 108 (1998) 664
60. Boese A.D., and Martin J.M.L. Chem. Phys. 121 (2004) 3405
61. Zhurko G.A., and Zhurko D.A. ChemCraft version 1.5 (2005)
62. Reed A.E., Weinstock R.B., and Weinhold F.A. J. Chem. Phys. 83 (1985) 735
63. Montgomery Jr. J.A., Frisch M.J., Ochterski J.W., and Petersson G.A. J. Chem. Phys. 110 (1999) 2822
64. Montgomery Jr. J.A., Frisch M.J., Ochterski J.W., and Petersson G.A. J. Chem. Phys. 112 (2000) 6532
65. Pokon E.K., Liptak M.D., Feldgus S., and Shields G.C. J. Phys. Chem. A 105 (2001) 10483
66. Cramer C.J. Essential of Computational Chemistry: Theories and Methods (2002), Wiley, New York
67. Miertus S., Scrocco E., and Tomasi J. J. Chem. Phys. 55 (1981) 117
68. Tomasi J., and Persico M. Chem. Rev. 94 (1994) 2027
69. Cammi R., and Tomasi J. J. Comput. Chem. 16 (1995) 1449
70. Cossi M., Barone V., Cammi R., and Tomasi J. J. Chem. Phys. Lett. 255 (1996) 327
71. Bachorz R.A., Rak J., and Gutowski M. Phys. Chem. Chem. Phys. 7 (2005) 2116
72. Kryachko E., Nguyen M.T., and Zeegers-Huyskens T. J. Phys. Chem. A 105 (2001) 1288
73. Ha T.K., Keller H.J., Gunde R., and Gunthard H.H. J. Phys. Chem. B 103 (1999) 6612
74. Mourik T.V., Price S.L., and Clary D.C. J. Phys. Chem. A 103 (1999) 1611