Structure of radicals from X-irradiated guanine derivatives. 2. An experimental and computational study of 9-ethylguanine single crystals

Journal of Physical Chemistry B

Volumn 111, Issue 27, 2007, Pages 7887-7896

  Jayatilaka, Nayana ^a   Nelson, William H ^a  

^a GEORGIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; HYDROGENATION; IRRADIATION; MOLECULAR STRUCTURE; PARAMAGNETIC RESONANCE; PROTONATION;

NITROGEN HYPERFINE INTERACTIONS; POSITIVE ISOTROPIC COMPONENTS; PRIMARY ELECTRONS;

CRYSTALLINE MATERIALS;

EID: 34547425472     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0712147     Document Type: Article

References (68)

1. (a) Zhang, J. D.; Xie, Y.; Schaefer, H. F. J. Phys. Chem. A 2006, 110, 12010.
2. (b) Mazurkiewicz, K.; Haranczyk, M.; Gutowski, M.; Rak, J.; Radisic, D.; Eustis, S. N.; Wang, D.; Bowen, K. H. J. Am. Chem. Soc. 2007, 129 (5), 1216-1224.
3. (a) Haranczyk, M.; Gutowski, M. Angew. Chem., Int. Ed. 2005, 44, 6585.
4. (b) Haranczyk, M.; Gutowski, M. J. Am. Chem. Soc. 2005, 127, 699.
5. Wang, W.; Sevilla, M. D. Radiat. Res. 1994, 138, 9.
6. Boudaiffa, B.; Cloutier, P.; Hunting, D.; Huels, M. A.; Sanche, L. Science 2000, 287, 1658.
7. Zheng, Y.; Cloutier, P.; Hunting, D. J.; Sanche, L.; Wagner, J. R. J. Am. Chem. Soc. 2005, 127, 16592.
8. Zheng, Y.; Wagner, J. R.; Sanche, L. Phys. Rev. Lett. 2006, 96, 208101/1.
9. (a) Dertinger, H. Z. Naturforsch., B 1967, 22, 1261.
10. (b) Alexander, C., Jr.; Gordy, W. Proc. Natl. Acad. Sci. U.S.A. 1967, 58, 1279.
11. (c) Strand, P.; Sagstuen, E.; Lehner, T.; Hüttermann, J. Int. J. Radiât. Biol. 1987, 51, 303.
12. (a) Close, D. M.; Sagstuen, E.; Nelson, W. H. J. Chem. Phys. 1985, 82, 4386.
13. (b) Close, D. M.; Nelson, W. H.; Sagstuen, E. Radiat. Res. 1987, 112, 283.
14. (c) Hole, E. O.; Sagstuen, E.; Nelson, W. H.; Close, D. M. Radiat. Res. 1991, 125, 119.
15. (a) Close, D. M.; Sagstuen, E.; Nelson, W. H. Radiat. Res. 1988, 116, 379.
16. (b) Sagstuen, E.; Hole, E. O.; Nelson, W. H.; Close, D. M. Radat. Res. 1988, 116, 196.
17. Nelson, W. H.; Hole, E. O.; Sagstuen, E.; Close, D. M. Int. J. Radiat. Biol. 1988, 54, 963.
18. Hole, E. O.; Nelson, W. H.; Close, D. M.; Sagstuen, E. J. Chem. Phys. 1987, 86, 5218.
19. Hole, E. O.; Sagstuen, E. Radiat. Res. 1987, 109, 190.
20. Hole, E. O.; Nelson, W. H.; Sagstuen, E.; Close, D. M. Radiat. Res. 1992, 129, 119.
21. Hole, E. O.; Sagstuen. E.; Nelson, W. H.; Close, D. M. Radiat. Res. 1992, 129, 1.
22. Kim, H.; Budzinski, E. E.; Box, H. C. J. Chem. Phys. 1989, 90, 1448.
23. Rakvin, B.; Herak, J. N. Radiat. Res. 1981, 88, 240.
24. Rakvin, B.; Herak, J. N.; Voit, K.; Hüttermann, J. Radiat. Environ. Biophys. 1987, 26, 1.
25. Jayatilaka, N.; Nelson, W. H. J. Phys. Chem. B 2007, 111, 800.
26. Gatzweiler, W.; Hüttermann, J.; Rupprecht, A. Radiat. Res. 1994, 138, 151.
27. Candeias, L. P.; Steenken, S. J. Am. Chem. Soc. 1989, 111, 1094.
28. Adhikary, A.; Kumar, A.; Becker, D.; Sevilla, M. D. J. Phys. Chem. B 2006, 110, 24171.
29. (a) Roehrig, G. H.; Oyler, N. A.; Adamowicz, L. Chem. Phys. Lett. 1994, 225, 265.
30. (b) Richardson, N. A.; Gu, J.; Wang, S.; Xie, Y.; Schaefer, H. F., III. J. Am. Chem. Soc. 2004, 126, 4404.
31. (c) Aflatooni, K.; Gallup, G. A.; Burrow, P. D. J. Phys. Chem. A 1998, 102, 6205.
32. (a) Sevilla, M. D.; Mohan, P. A. Int. J. Radiat. Biol. 1974, 25, 635.
33. (b) Li, X.; Cai, Z.; Sevilla, M. D. J. Phys. Chem. A 2002, 106, 1596.
34. (c) Colson, A. O.; Besler, B.; Sevilla, M. D. J. Phys. Chem. 1993, 97, 13852
35. Nese, C.; Yuan, Z.; Schuchmann. M. N.; Sonntag, C. v. Int. J. Radiat. Biol. 1992, 62, 527.
36. 2O trapped in the NMR solvent readily exchanges with the deuterons at the N1 and N2 sites; this can be significant at the low solute concentrations used for the NMR measurements. Thus, the NMR results for these positions probably underestimate the deuteration at these postions in the crystals.
37. Destro, R.; Kistenmacher, T. J.; Marsh, R. E. Acta Crystallogr. 1974, B30, 79.
38. The analysis also indicated a degree of disorder involving the terminal methyl group of molecule B. This is not an issue since none of the radicals to be discussed below involve this methyl group.
39. Actually, the molecules are slightly tilted with respect to the cristallographic plane, by less than 5°.
40. Schonland, D. S. Proc. Phys. Soc. 1959, 73, 788.
41. Nelson, W. H. J. Magn. Reson. 1980, 38, 71.
42. Busing, W. R.; Martin, K. O.; Levy, H. A. ORFEE - A Fortran Crystallographic Function and Error Program; ORNL-TM-306, Oak Ridge Natl. Labs: Oak Ridge, TN, 1964.
43. (a) Duling, D. R.; Motten, A. G.; Mason, R. P. J. Magn. Reson. 1988, 77, 504
44. (b) Duling, D. R. J. Magn. Reson. 1994, B104, 105.
45. Tokdemir, S.; Nelson, W. H. J. Phys. Chem. A 2005, 109, 8732.
46. 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, rev. B.04 ed.; Gaussian Inc.: Pittsburgh. PA, 2003.
47. Parr. R. G.; Yang, W. Density-functional theory of atoms and molecules; Oxford University Press: New York. 1989.
48. Becke, A. D. J. Chem. Phys. 1996, 104, 1040.
49. Pauwels, E.; Van Speybroeck, V.; Vanhaelewyn, G.; Callens, F.; Waroquier, M. Int. J. Quantum Chem. 2004, 99, 102.
50. Actually, when the field is along 〈a〉, it is 3.8° from the normal to the plane.
51. The type N ENDOR at the lower right also suggests other interactions by the presence of weak features in the ENDOR such as those spanning 45-48 MHz. However, these features disappeared on rotating the crystals and could not be studied further. As will be shown in the following discussion, the major EPR features are accounted for by radicals R1 and R2.
52. McConnell, H. M.; Chesnut, D. B. J. Chem. Phys. 1958, 25, 107.
53. (a) Ngo, Q.; Budzinski, E. E.; Box. H. C. J. Chem. Phys. 1974, 60, 3373.
54. (b) Nelson, W. H.; Gill, C. D. Mol. Phys. 1978, 36, 1779.
55. Bernhard, W. A. J. Chem. Phys. 1984, 81, 5928.
56. Gordy, W. Theory and Applications of Electron Spin Resonance; Wiley: New York, 1980; Vol. 15.
57. Erling, P. A.; Nelson, W. H. J. Phys. Chem. A 2004, 108, 7591.
58. Table 1 lists estimated values for the nitrogen hyperfine couplings, and the computations also provide nitrogen couplings. Table 1 of the Supporting Information lists the experimental estimates for R1 along with the values from the various computations. The experimental and computed dipolar results are generally consistent, but there are some differences for the isotropic values.
59. All atomic coordinates used for these calculations were derived from the crystal structure. To reduce the computational load, the ethyl group connected to N9 was replaced with an H in all cases and the computations were performed at B3LYP//6-311G(2df,p)/6-31G(2d,p) with no diffuse functions in the basis sets.
60. (a) Wetmore, S. D.; Boyd, R. J.; Eriksson, L. A. J. Phys. Chem. B 1998, 102, 9332.
61. (b) Weiland, B.; Hüttermann, J.; Van Toi, J. Acta Chem. Scand. 1997, 51, 585.
62. We note that the isotropic components of the couplings predicted for HN2 and H′N2 are very large in the optimized structure. This reflects distortion in the bonds to C2, the large spin density at that site, and that the amino hydrogens are twisted about the C2-N2 bond so that one is nearly normal to the N1-C2-N3 plane. Manual adjustment of the amino group to make all atoms lie in the N1-C2-N3 plane led to the results shown in the last entry of Table 3. Although the adjustment eliminated the large isotropic character of the amino proton couplings, the coupling predicted for HC8 is still small enough to eliminate this structure as a candidate for R2.
63. Flossmann, W.; Westhof, E.; Müller, A. Int. J. Rad. Biol. 1974, 25, 437.
64. Tokdemir, S.; Nelson, W. H. J. Phys. Chem. A 2006, 110, 6552.
65. Nelson, W. H.; Sagstuen, E.; Hole, E. O.; Close, D. M. Radiat. Res. 1998, 149, 75.
66. (a) Gordy, W.; McCormick, C. G. J. Am Chem. Soc. 1956, 78, 3243.
67. (b) McDowell, C. A.; Raghunathan, P.; Shimokoshi, K. J. Chem. Phys. 1973, 58, 114.
68. (c) Fessenden, R. W.; Schuler, R. H. J. Chem. Phys. 1963, 39, 2147.