[en] The elusive hydrogen atom adduct to the N-1 position in adenine, which is thought to be the initial intermediate of chemical damage, was specifically generated in the gas phase and characterized by neutralization-reionization mass spectrometry. The N-1 ad
Becker, D.; Sevilla, M. D. In Advances in Radiation Biology. DNA and Chromatin Damage Caused by Radiation; Lett, J. T., Sinclair, W. K., Eds.; Academic Press: San Diego, CA, 1993; Vol. 17, pp 121-180.
von Sonntag, C. In Physical and Chemical Mechanisms in Molecular Radiation Biology; Glass, W. A., Varma, M. N., Eds.; Plenum Press: New York, 1991; pp 287-321.
Chatterjee, A.; Holley, W. R. In Physical and Chemical Mechanisms in Molecular Radiation Biology; Glass, W. A., Varma, M. N., Eds.; Plenum Press: New York, 1991; pp 257-285.
(a) Holmes, D. E.; Ingalls, R. B.; Myers, L. S., Jr. Int. J. Radiat. Biol. 1967, 13, 225-234.
(b) Moorthy, P. N.; Hayon, E. J. Am. Chem. Soc. 1975, 97, 3345-3350.
(c) Hissung, A.; von Sonntag, C.; Veltwisch, D.; Asmus, K.-D. Int. J. Radiat. Biol. 1981, 39, 63-71.
(d) Visscher, K. J.; De Haas, M. P.; Loman, H.; Vojnovic, B.; Warman, J. M. Int. J. Radiat. Biol. 1987, 52, 745-753.
(e) Visscher, K. J.; Hom, M.; Loman, H.; Spoelder, H. J. W.; Verberne, J. B. Radiat. Phys. Chem. 1988, 32, 465-473.
(f) Candeias, L. P.; Steenken, S. J. Phys. Chem. 1992, 96, 937-944.
(g) Schaefer, A.; Hüttermann, J.; Kraft, G. Int. J. Radiat. Biol. 1993, 63, 139-149.
(h) Nelson, W. H.; Sagstuen, E.; Hole, E. O.; Close, D. M. Radiat. Res. 1992, 131, 272-284.
For a review see: (i) Steenken, S. Chem Rev. 1989, 89, 503-520
(a) Zehner, H.; Flossmann, W.; Westhof, E. Z. Naturforsch. 1976, 31C, 225-231.
(b) Zehner, H.; Westhof, E.; Flossmann, W.; Mueller, A. Z. Naturforsch. 1977, 32C, 1-10.
(d) Kar, L.; Bernhard, W. A. Radiat. Res. 1983, 93, 232-253.
(e) Close, D. M.; Nelson, W. H. Radiat. Res. 1989, 117, 367-378.
(a) Sevilla, M. D.; Failor, R.; Clark, C.; Holroud, R. A.; Pettei, M. J. Phys. Chem. 1976, 80, 353-358.
(b) Barnes, J.; Bernhard, W. A. J. Phys. Chem. 1993, 97, 3401-3408.
(c) Barnes, J.; Bernhard, W. A. J. Phys. Chem. 1994, 98, 10969-10977.
(a) Nguyen, V. Q.; Tureček, F. J. Mass Spectrom. 1996, 31, 1173-1184.
(b) Nguyen, V. Q.; Tureček, F. J. Mass Spectrom. 1997, 32, 55-63.
(c) Nguyen, V. Q.; Tureček, .F J. Am. Chem. Soc. 1997, 119, 2280-2290.
(d) Tureček, F. J. Mass Spectrom. 1998, 33, 779-795.
(e) Wolken, J. K.; Tureček, F. J. Phys. Chem. A 1999, 103, 1905-1912.
(f) Wolken, J. K.; Tureček, F. J. Am. Chem. Soc. 1999. 121, 6010-6018.
(g) Wolken, J. K.; Tureček, F. J. Phys. Chem. A 1999, 103, 6268-6281.
(a) Wolken, J. K.; Syrstad, E. A.; Vivekananda, S.; Tureček, F. J. Am. Chem. Soc. 2001, 123, 5804-5805.
(b) Syrstad, E. A.; Vivekananda, S.; Tureček, F. J. Phys. Chem. A 2001, 105, 8339-8351.
(c) Wolken, J. K.; Tureček, F. J. Phys. Chem. A 2001, 105, 8352-8360.
(a) Wolken, J. K.; Tureček, F. J. Am. Soc. Mass Spectrom. 2000 11, 1065-1071.
(b) Chen, X.; Syrstad, E. A.; Nguyen, M. T.; Gerbaux, P.; Tureček, F. J. Phys. Chem. A 2004, 108, 9283-9293.
(a) Curtis, P. M.; Williams, B. W.; Porter, R. F. Chem. Phys. Lett. 1979, 65, 296-299.
(b) Burgers, P. C.; Holmes, J. L.; Mommers, A. A.; Terlouw, J. K. Chem. Phys. Lett. 1983, 102, 1-3.
(c) Danis, P. O.; Wesdemiotis, C.; McLafferty, F. W. J. Am. Chem. Soc. 1983, 105, 7454-7456.
For most recent reviews see: (d) Zagorevskii, D. V. In Comprehensive Coordination Chemistry II; McCleverty, J. A., Meyer, T. J., Eds.; Elsevier: Oxford, UK, 2004; pp 381-386.
(e) Tureček, F. Top. Curr. Chem. 2003, 225, 77-129.
(f) Tureček, F. In Encyclopedia of Mass Spectrometry; Armentrout, P. B., Ed.; Elsevier: Amsterdam, The Netherlands, 2003; Vol. 1, Chapter 7, pp 528-541.
(g) Zagorevskii, D. V. Coord. Chem. Rev. 2002, 225, 5-34.
(h) Gerbaux, P.; Wentrup, C.; Flammang, R. Mass Spectrom. Rev. 2000, 19, 367-389.
(i) Zagorevskii, D. V.; Holmes, J. L. Mass Spectrom. Rev. 1999, 18, 87-118.
(a) Sadílek, M.; Tureček, F. J. Phys. Chem. 1996, 100, 9610-9614.
(b) Sadfí.ek, M.; Tureček, F. Chem. Phys. Lett. 1996, 263, 203-208.
(c) Polášek, M.; Tureček, F. J. Phys. Chem. A 2001, 105, 1371-1382.
(a) Kuhns, D. W.; Tran, T. B.; Shaffer, S. A.; Tureček, F. J. Phys. Chem. 1994, 95, 4845-4853.
(b) Kuhns, D. W.; Tureček, F. Org. Mass Spectrom. 1994, 29, 463-469.
(c) Sadílek, M.; Tureček, F. J. Phys. Chem. 1996, 100, 224-232.
Laxer, A.; Major, D. T.; Gottlieb, H. E.; Fischer, B. J. Org. Chem. 2001, 66, 5463-5481.
(a) Tureček, F.; Gu, M.; Shaffer, S. A. J. Am. Soc. Mass Spectrom. 1992, 3, 493-501.
(b) Tureček, F. Org. Mass Spectrom. 1992, 27, 1087-1097.
Seymour, J. L.; Syrstad, E. A.; Langley, C. C.; Tureček, F. Int. J. Mass Spectrom. 2003, 225, 687-702.
Shaffer, S. A.; Tang, K.; Anderson, G. A.; Prior, D. C.; Udseth, H. R.; Smith, R. D. Rapid Commun. Mass Spectrom. 1997, 11, 1813-1817.
Bateman, R. H.; Brown, J.; Lefevere, M.; Flammang, R.; Van Haverbeke, Y. Int. J. Mass Spectrom Ion Processes 1992, 115, 205-218.
(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.; 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.
(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.; Kiene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austn, 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.
(a) Becke, A. D. J. Chem. Phys. 1993, 98, 1372-1377.
(b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
(c) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627.
(a) Schlegel, H. B. J. Chem. Phys. 1986, 84, 4530-4534.
(b) Mayer, I. Adv. Quantum Chem. 1980, 12, 189-262.
Tureček, F. J. Phys. Chem. A 1998, 102, 4703-4713.
(a) Tureček, F.; Carpenter, F. H.; Polce, M. J.; Wesdemiotis, C. J. Am. Chem. Soc. 1999, 121, 7955-7956.
(b) Tureček, F.; Polášek, M.; Frank, A. J.; Sadílek. M. J. Am. Chem. Soc. 2000, 122, 2361-2370.
(c) Polášek, M.; Tureček, F. J. Am. Chem. Soc. 2000, 122, 9511-9524.
(d) Tureček, F.; Syrstad, E. A. J. Am. Chem. Soc. 2003, 125, 3353-3369.
(e) Tureček, F.; Yao, C. J. Phys. Chem. A 2003, 107, 9221-9231.
(a) Rablen, P. R.; Bentrup, K. H. J. Am. Chem. Soc. 2003, 125, 2142-2147.
(b) Rablen, P. R. J. Org. Chem. 2000, 65, 7930-7937.
(c) Rablen, P. R. J. Am. Chem. Soc. 2000, 122, 357-368.
(d) Hirama, M.; Tokosumi, T.; Ishida, T.; Aihara, J. Chem. Phys. 2004, 305, 307-316.
Čížek, J.; Paldus, J.; Šroubková, L. Int. J. Quantum Chem. 1969, 3, 149-167.
Purvis, G. D.; Bartlett, R. J. J. Chem. Phys. 1982, 76, 1910-1918.
Curtiss, L. A.; Raghavachari, K.; Pople, J. A. J. Chem. Phys. 1993, 98, 1293-1298.
Stratmann, R. E.; Scuseria, G. E.; Frisch, M. J. J. Chem. Phys. 1998, 109, 8218-8224.
(a) Barone, V.; Cossi, M.; Tomasi, J. J. Chem. Phys. 1997, 107, 3210-3221.
(b) Cossi, M.; Scalmani, G.; Rega, N.; Barone, V. J. Chem. Phys. 2002, 117, 43-54.
Zhu, L.; Hase, W. L. Quantum Chemistry Program Exchange; Indiana University: Bloomington, IN, 1994; Program No. QCPE 644.
Frank, A. J.; Sadílek, M.; Ferrier, J. G.; Tureček, F. J. Am. Chem. Soc. 1997, 119, 12343-12353.
Gilbert, R. G.; Smith, S. C. Theory of Unimolecular and Recombination Reactions; Blackwell Scientific Publications: Oxford, UK, 1990; pp 52-132.
Tureček, F.; Syrstad, E. A. J. Am. Chem. Soc. 2003, 125, 3353-3369.
(a) Syrstad, E. A.; Stephens, D. D.; Tureček, F. J. Phys. Chem. A 2003, 107, 115-126.
(b) Chen, X.; Syrstad, E. A.; Tureček, F. J. Phys. Chem. A 2004, 108, 4163-4173.
Truhlar, D. G.; Kuppermann, A. J. Am. Chem. Soc. 1971, 93, 1840-1851.
Eckart, C. Phys. Rev. 1930, 35, 1303-1309.
Bell, R. P. The Tunnel Effect in Chemistry; Chapman and Hall: London, UK, 1980; p 27.
Major, D. T.; Laxer, A.; Fischer, B. J. Org. Chem. 2002, 67, 790-802.
Christensen, J. J.; Rytting, J. H.; Izatt, R. M. Biochemistry 1970, 9, 4907-4913.
Tureček, F.; Chen, X. J. Am. Soc. Mass Spectrom. 2005, 16, 1713-1726.
(a) Gatlin, C. L.; Tureček, F. Anal. Chem. 1994, 66, 712-718.
For a review, see: (b) Van Berkel, G. J. In Electrospray Ionization Mass Spectrometry; Cole, R. B., Ed.; John Wiley & Sons: New York, 1997; Chapter 2, pp 65-106.
(a) Drahos, L.; Heeren, R. M. A.; Collette, C.; De Pauw, E.; Vekey, K. J. Mass Spectrom. 1999, 34, 1373-1379.
(b) Naban-Maillet, J.; Lesage, D.; Bossee, A.; Gimbert, Y.; Sztaray, J.; Vekey, K. J. Mass Spectrom. 2005, 40, 1-8.
Nelson, C. C.; McCloskey, J. A. J. Am. Chem. Soc. 1992, 114, 3661-3668.
From the corresponding proton affinities (kJ mol -1) of water (691) and methanol (754). NIST Standard Reference Database Number 69, March, 2003 Release: http://webbook.nist.gov/chemistry
Harrison, A. G. Chemical Ionization mass Spectrometry, 2nd ed.; CRC Press: Boca Raton, FL, 1992; p 30.
See the NIST database (ref 43) for the reference electron-ionization mass spectrum of adenine.
(b) Wetmore, S. D.; Boyd, R. J.; Eriksson, L. A. J. Phys. Chem. B 1998, 102, 10602-10614.
Fitch, W. L.; Sauter, A. D. Anal. Chem. 1983, 55, 832-835.
Lifshitz, C. Mass Spectrom. Rev. 1982, 1, 309-348.
(a) Gerbaux, P.; Tureček, F. J. Phys. Chem. A 2002, 106, 5938-5950.
(b) Tureček, F. Int. J. Mass Spectrom. 2003, 227, 327-338.
Calculations of reliable transition state energies for H-atom transfer between 1 and adenine would require a high-level theory that is beyond our present computational capabilities.