Metal-mediated formation of gas-phase amino acid radical cations

Journal of Physical Chemistry A

Volumn 110, Issue 27, 2006, Pages 8304-8315

  Barlow, Christopher K ^a   Moran, Damian ^b   Radom, Leo ^b,d   McFadyen, W David ^a   O'Hair, Richard A J ^a,c,d  

^a UNIVERSITY OF MELBOURNE   (Australia)

^b UNIVERSITY OF SYDNEY   (Australia)

^c UNIVERSITY OF MELBOURNE   (Australia)

^d Australian Government Australian Research Council   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ARGININE RADICAL CATION; COLLISION-INDUCED DISSOCIATION (CID); HISTIDINE; TERNARY COMPLEX;

CHEMICAL REACTIONS; DISSOCIATION; METAL FORMING; OXIDATION; POSITIVE IONS;

AMINO ACIDS;

AMINO ACID; CATION; FREE RADICAL; METAL;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; CONFORMATION; MASS SPECTROMETRY; OXIDATION REDUCTION REACTION;

AMINO ACIDS; CATIONS; FREE RADICALS; MASS SPECTROMETRY; METALS; MODELS, CHEMICAL; MOLECULAR CONFORMATION; OXIDATION-REDUCTION;

EID: 33746418924     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp056471v     Document Type: Article

References (50)

1. Hu, P.; Loo, J. A. J. Am. Chem. Soc. 1995, 117, 11314.
2. Gatlin, C. L.; Tureček, F.; Vaisar, T. J. Mass Spectrom. 1995, 30, 1617.
3. Gatlin, C. L.; Tureček, F.; Vaisar, T. J. Mass Spectrom, 1995, 30, 1605.
4. Gatlin, C. L.; Tureček, F.; Vaisar, T. J. Am. Chem. Soc. 1995, 117, 3637.
5. Lavanant, H.; Hecquet, E.; Hoppilliard, Y. Int. J. Mass Spectrom. 1999, 185/186/187, 11.
6. Chu, I. K.; Rodriquez, C. F.; Lau, T. C.; Hopkinson, A. C.; Siu, K. W. M. J. Phys. Chem. B 2000, 104, 3393.
7. Chu, I. K.; Rodriguez, C. F.; Hopkinson, A. C.; Siu, K. W. M. J. Am. Soc. Mass Spectrom. 2001, 12, 1114.
8. Wee, S.; O'Hair, R. A. J.; McFadyen, W. D. Rapid Commun. Mass Spectrom. 2002, 16, 884.
9. Chu, I. K.; Siu, S. O.; Lam, C. N. W.; Chan, J. C. Y.; Rodriquez, C. F. Rapid Commun. Mass Spectrom. 2004, 78, 1798.
10. Bagheri-Majdi, E.; Ke, Y.; Orlova, G.; Chu, I. K.; Hopkinson, A. C.; Siu, K. W. M. J. Phys. Chem. B 2004, 108, 11170.
11. Barlow, C. K.; Wee, S.; McFadyen, W. D.; O'Hair, R. A. J. Dalton Trans. 2004, 3199.
12. Chu, I. K.; Lam, C. N. W.; Siu, S. O. J. Am. Soc. Mass Spectrom. 2005, 16, 763.
13. Wee, S.; O'Hair, R. A. J.; McFadyen, W. D. Int. J. Mass Spectrom. 2004, 234, 101.
14. Wee, S.; White, J. M.; McFadyen, W. D.; O'Hair, R. A. J. Aust. J. Chem. 2003, 56, 1201.
15. Wee, S.; O'Hair, R. A. J.; McFadyen, W. D. Int. J. Mass Spectrom. 2006, 249-250, 171.
16. Barlow, C. K.; McFadyen, W. D.; O'Hair, R. A. J. J. Am. Chem. Soc. 2005, 127, 6109.
17. (a) Junk, G.; Svec, H. J. Am. Chem. Soc. 1963, 85, 839.
18. (b) Biemann, K.; Seibl, J.; Gapp, F. J. Am. Chem. Soc. 1961, 83, 3795.
19. (c) Biemann, K.; McCloskey, J. A. J. Am. Chem. Soc. 1962, 84, 3192.
20. (d) Heyns, K.; Gruetzmacher, H. F. Liebigs Ann. Chem. 1963, 667, 194.
21. (e) For evaluated EI-MS data, see the National Institute of Standards and Technology Chemistry WebBook at http://webbook.nist.gov/chemistry/.
22. (a) Grotemeyer, J.; Walter, K.; Boesl, U.; Schlag, E. W. Int. J. Mass Spectrom. Ion Processes 1987, 78, 69.
23. (b) Koester, C.; Grotemeyer, J. Org. Mass Spectrom. 1992, 27, 463.
24. (c) Nagra, D. S.; Zhang, J. Y.; Li, L. Anal. Chem. 1991, 63, 2188.
25. (d) Vorsa, V.; Kono, T.; Willey, K. F.; Winograd, N. J. Phys. Chem. B 1999, 103, 7889.
26. Detailed comparisons of the fragmentation reactions of radical cations of amino acids formed from metal complexes with those formed via El or photoionization are difficult, due to the quite different energy and time regimes for the various ionization techniques. The ideal study would be to experimentally determine the kinetics of fragmentation upon excitation of long-lived, thermalized radical cations and to then model the kinetics using RRKM calculations. Professor Lifshitz recently pioneered such studies (for example, see: Hu, Y.; Hadas, B.; Davidovitz, M.; Balta, B.; Lifshitz, C. J. Phys. Chem. A 2003, 107, 6507), but these were curtailed by her untimely death.
27. Castro, I.; Faus, J.; Juive, M.; Gleizes, A. J. Chem. Soc., Dalton Trans. 1991, 1937.
28. Gerloch, M.; Lewis, J.; Mabbs, F. E.; Richards, A. J. Chem. Soc. A 1968, 112.
29. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502.
30. Spartan 02; Wavefunction, Inc., Irvine, CA. Except for molecular mechanics and semiempirical models, the calculation methods used in Spartan 02 have been documented in Kong, J.; White, C. A.; Krylov, A. I.; Sherrill, D.; Adamson, R. D.; Furlani, T. R.; Lee, M. S.; Lee, A. M.; Gwaltney, S. R.; Adams, T. R.; Ochsenfeld, C.; Gilbert, A. T. B.; Kedziora, G. S.; Rassolov, V. A.; Maurice, D. R.; Nair, N.; Shao, Y.; Besley, N. A.; Maslen, P. E.; Dombroski, J. P.; Daschel, H.; Zhang, W.; Korambath, P. P.; Baker, J.; Byrd, E. F. C.; Van Voorhis, T.; Oumi, M.; Hirata, S.; Hsu, C.-P.; Ishikawa, N.; Florian, J.; Warshel, A.; Johnson, B. G.; Gill, P. M. W.; Head-Gordon, M.; Pople, J. A. J. Comput. Chem. 2000, 27, 1532.
31. A discussion and assessment of commonly used calculation methods may be found in Hehre, W. J. A Guide to Molecular Mechanics and Quantum Chemical Calculations; Wavefunction: Irvine, 2002.
32. 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.; Bakken, V.; 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.; and Pople, J. A. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
33. Campbell, S.; Beauchamp, J. L.; Rempe, M.; Lichtenberger, D. L. Int. J. Mass Spectrom. Ion Processes 1992, 117, 83.
34. Lee, K. T.; Sung, J.; Lee, K. J.; Park, Y. D.; Kim, S. K. Angew. Chem., Int. Ed. 2002, 41, 4114.
35. O'Hair, R. A. J.; Reid, G. E. Rapid Commun. Mass Spectrom. 2000, 14, 1220.
36. Dookeran, N. N.; Yalcin, T.; Harrison, A. G. J. Mass Spectrom. 1996, 37, 500.
37. O'Hair, R. A. J. J. Mass Spectrom. 2000, 35, 1377.
38. Rogalewicz, F.; Hoppilliard, Y.; Ohanessian, G. Int. J. Mass Spectrom. 2000, 195/196, 565.
39. 2+ complexes, as discussed in the Experimental Section.
40. Tureček, F.; Kerwin, J. L.; Xu, R.; Kramer, K. J. J. Mass Spectrom. 1998, 33, 392.
41. Further details will be published separately. We note that a complete theoretical description of all possible fragmentation reactions of the radical cations of the larger amino acids would be a computationally demanding proposition due to the large conformational space and the existence of multiple tautomeric structures. Indeed, the theoretical treatment of even the simplest amino acid, glycine, is complicated by the existence of multiple conformations and tautomers. See: Lu, H.-F.; Li, F.-Y.; Lin, S. H. J. Phys. Chem. A 2004, 108, 9233.
42. Price, W. D.; Jockusch, R. A.; Williams, E. R. J. Am. Chem. Soc. 1997, 119, 11988.
43. Chapo, C. J.; Paul, J. B.; Provencal, R. A.; Roth, K.; Saykally, R. J. J. Am. Chem. Soc. 1998, 120, 12956.
44. Maksic, Z. B.; Kovacevic, B. J. Chem. Soc., Perkin Trans 2 1999, 2623.
45. Skurski, P.; Gutowski, M.; Barrios, R.; Simons, J. Chem. Phys. Lett. 2001, 337, 143.
46. Rak, J.; Skurski, P.; Simons, J.; Gutowski, M. J. Am. Chem. Soc. 2001, 123, 11695.
47. Gdanitz, R. J.; Cardoen, W.; Windus, T. L.; Simons, J. J. Phys. Chem. A 2004, 108, 515.
48. Jockusch, R. A.; Price, W. D.; Williams, E. R. J. Phys. Chem. A 1999, 103, 9266.
49. Cerda, B. A.; Wesdemiotis, C. Analyst 2000, 125, 657.
50. Viehe, H. G.; Janousek, Z.; Merenyi, R.; Stella, L. Acc. Chem. Res. 1985, 18, 148.