H-Atom abstraction by C-centered radicals from cyclic and acyclic dipeptides. A theoretical and experimental study of reaction rates

Physical Chemistry Chemical Physics

Volumn 5, Issue 15, 2003, Pages 3278-3288

  Reid, Darren L ^a,c   Armstrong, David A ^a   Rauk, Arvi ^a   Nese, Chandrasekhar ^b   Schuchmann, Man Nien ^b   Westhoff, Ursula ^b   Von Sonntag, Clemens ^b,d  

^a UNIVERSITY OF CALGARY   (Canada)

^b MAX PLANCK INSTITUTE FOR CHEMICAL ENERGY CONVERSION   (Germany)

^c PFIZER INC   (United States)

^d LEIBNIZ INSTITUTE OF SURFACE ENGINEERING IOM   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACID ANHYDRIDE; ALANINE; CARBON; DIPEPTIDE; GLYCINE; HYDROGEN; PEPTIDE;

ARTICLE; CALCULATION; CHEMICAL INTERACTION; CHEMICAL REACTION; COMPUTER ANALYSIS; DOSE RESPONSE; KINETICS; POLARIZATION; PROTON TRANSPORT; PULSE RADIOLYSIS; RADIATION; THEORETICAL MODEL;

EID: 0042697197     PISSN: 14639076     EISSN: None     Source Type: Journal    
DOI: 10.1039/b303223j     Document Type: Article

References (63)

1. A. Rauk, D. Yu, J. Taylor, G. V. Shustov, D. A. Block and D. A. Armstrong, Biochemistry, 1999, 38, 9089.
2. D. A. Armstrong, D. Yu and A. Rauk, Can. J. Chem., 1996, 74, 1192.
3. D. A. Block, D. Yu, D. A. Armstrong and A. Rauk, Can. J. Chem., 1998, 76, 1042.
4. A. Rauk, D. Yu and D. A. Armstrong, J. Am. Chem. Soc., 1998, 120, 8848.
5. J. Berkowitz, G. B. Ellison and D. Gutman, J. Phys. Chem., 1994, 98, 2744.
6. D. A. Block, D. A. Armstrong and A. Rauk, J. Phys. Chem. A, 1999, 103, 3562.
7. A. Rauk, D. Yu and D. A. Armstrong, J. Am. Chem. Soc., 1997, 119, 208.
8. M. Jonsson, D. D. M. Wayner, D. A. Armstrong, D. Yu and A. Rauk, J. Chem. Soc., Perkin Trans. 2., 1998, 1967.
9. D. A. Armstrong, D. Yu and A. Rauk, Can. J. Chem., 1996, 74, 1192.
10. H. G. Viehe, Z. Janousek, R. Merenyi and L. Stella, Acc. Chem. Res., 1985, 18, 148.
11. K. J. Laidler, Chemical Kinetics, McGraw-Hill, New York, 1965, pp. 133-135.
12. C. von Sonntag, The Chemical Basis of Radiation Biology, Taylor & Francis, London, 1987, pp. 353-374.
13. D. L. Reid, G. V. Shustov, D. A. Armstrong, A. Rauk, M. N. Schuchmann, M. S. Akhlaq and C. von Sonntag, Phys. Chem. Chem. Phys., 2002, 4, 2965-2974.
14. O. J. Mieden and C. von Sonntag, J. Chem. Soc. Perkin Trans. 2, 1989, 2071.
15. O. J. Mieden and C. von Sonntag, Z. Naturforsch., Tell B, 1989, 44, 959.
16. O. J. Mieden, M. N. Schuchmann and C. von Sonntag, J. Phys. Chem., 1993, 97, 3783.
17. R. F. W. Bader, Atoms in Molecules. A Quantum Theory, Clarendon, Oxford, 1990.
18. A. Rauk, Orbital Interaction Theory of Organic Chemistry, John Wiley & Sons, Inc., Toronto, 2nd edn., 2001.
19. I. Fleming, Frontier Orbitals and Organic Chemical Reactions, John Wiley & Sons, Toronto, 1990.
20. C. von Sonntag and H. -P. Schuchmann, Methods Enzymol., 1994, 233, 3.
21. F. Weeke, E. Bastian and G. Schomburg, Chromatographia, 1974, 7, 163.
22. D. Veltwisch, E. Janata and K. -D. Asmus, J. Chem. Soc., Perkin Trans. 2, 1980, 146.
23. K. -D. Asmus, H. Möckel and A. Henglein, J. Phys. Chem., 1973, 77, 1218.
24. V. M. Berdnikov, N. M. Bazhin, V. K. Fedorov and O. V. Polyakov, Kinet. Catal. (Engl. Transl.), 1972, 13, 986.
25. B. C. Gilbert, R. G. G. Holmes, H. A. H. Laue and R. O. C. Norman, J. Chem. Soc., Perkin Trans. 2, 1976, 1047.
26. H. -P. Schuchmann and C. von Sonntag, J. Photochem., 1981, 16, 289.
27. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C, Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle and J. A. Pople, GAUSSIAN 98 (Revision A.7), Gaussian, Inc., Pittsburgh, PA, 1998.
28. M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, D. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, D. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez and J. A. Pople, GAUSSIAN 94, Revision B. 3, Gaussian, Inc., Pittsburgh, PA, 1995.
29. A. P. Scott and L. Radom, J. Phys. Chem., 1996, 100, 16502.
30. N. Kobko and J. J. Dannenberg, J. Phys. Chem. A., 2001, 105, 1944.
31. W. J. Hehre, R. Ditchfield, L. Radom and J. A. Pople, J. Am. Chem. Soc., 1970, 92, 4796.
32. D. A. Armstrong, D. Yu and A. Rauk, Can. J. Chem., 1996, 74, 1192.
33. J. Berkowitz, G. B. Ellison and D. Gutman, J. Phys. Chem., 1994, 98, 2744.
34. M. W. Chase, C. A. Davies, J. R. Downey, Jr., D. J. Frurip, R. A. McDonald and A. N. Syverud, JANAF Thermodynamic Tables, 3rd edn., J. Phys. Chem. Ref. Data, Suppl. 1, 1985, 14, 1-1856.
35. R. D. Johnson III and J. W. Hudgens, J. Phys. Chem., 1996, 100, 19874.
36. R. Atkinson, D. L. Baulch, R. A. Cox, R. F. Hampson, Jr., J. A. Kerr, M. J. Rossi and J. Troe, J. Phys. Chem. Ref. Data, 1997, 26, 1329.
37. G. K. Vemulapalli, Physical Chemistry, Prentice Hall, Englewood Cliffs, NJ, 1993.
38. J. I. Steinfeld, J. S. Francisco, and W. L. Hase, Chemical Kinetics and Dynamics, Prentice Hall, Upper Saddle River, NJ, 2nd edn., 1999, pp. 300-302.
39. E. P. Wigner, Z. Phys. Chem. Abt. B, 1932, 19, 203.
40. H. S. Johnston, Gas Phase Reaction Rate Theory, Ronald Press, New York, 1966.
41. B. C. Garrett and D. G. Truhlar, J. Phys. Chem., 1979, 83, 200.
42. D. A. McQuarrie, Statistical Thermodynamics, Harper & Row, New York, NY, 1973.
43. D. H. Wertz, J. Am. Chem. Soc., 1980, 102, 5316.
44. M. H. Abraham, J. Am. Chem. Soc., 1981, 103, 6742.
45. I. H. Williams, J. Am. Chem. Soc., 1987, 109, 6299.
46. J. Florián and A. Warshel, J. Phys. Chem. B, 1999, 103, 10282.
47. S. Wolfe, C.-K. Kim, K. Yang, N. Weinberg and Z. Shi, J. Am. Chem. Soc., 1995, 117, 4240.
48. Strictly speaking, hydration energies are free energies. However, we treat the temperature-independent components of free energies of solvation as enthalpies.
49. J. B. Foresman, T. A. Keith, K. B. Wiberg, J. Snoonian and M. J. Frisch, J. Phys. Chem., 1996, 100, 16098.
50. S. W. Benson, J. Am. Chem. Soc., 1958, 80, 5151.
51. E. Pollak and P. Pechukas, J. Am. Chem. Soc., 1978, 100, 2986.
52. D. R. Coulson, J. Am. Chem. Soc., 1978, 100, 2992.
53. J. P. Guthrie, J. Phys. Chem. A., 2001, 105, 8495.
54. S. W. Benson, Thermochemical Kinetics, Methods for the Estimation of Thermochemical Data and Rate Parameters, John Wiley & Sons, Toronto, 2nd edn., 1976.
55. P. Ulanski, G. Merényi, J. Lind, R. Wagner and C. von Sonntag, J. Chem. Soc., Perkin Trans. 2, 1999, 673.
56. K. B. Wiberg, J. R. Cheeseman, J. W. Ochterski and M. J. Frisch, J. Am. Chem. Soc., 1995, 117, 6535.
57. B. P. Roberts and A. J. Steel, J. Chem. Soc., Perkin Trans. 2, 1994, 2155.
58. B. P. Roberts, J. Chem. Soc., Perkin Trans. 2, 1996, 2719.
59. J. A. Kerr and A. F. Trotman-Dickenson, J. Chem. Soc., 1957, 3322.
60. G. Lenvag and T. Berces, J. Photochem. A, 1987, 40, 31.
61. G. Greig and J. C. Thynne, Trans. Faraday Soc., 1966, 62, 379.
62. J. K. Thomas, J. Phys. Chem., 1967, 71, 1919.
63. B. O. Leung, D. L. Reid, D. A. Armstrong, and A. Rauk, submitted for publication, and references therein.