Kinetic effects of hydrogen bonds on proton-coupled electron transfer from phenols

Journal of the American Chemical Society

Volumn 128, Issue 40, 2006, Pages 13076-13083

  Sjödin, Martin ^a,d   Irebo, Tania ^a   Utas, Josefin E ^b   Lind, Johan ^c   Merényi, Gabor ^c   Åkermark, Björn ^b   Hammarström, Leif ^a  

^a UPPSALA UNIVERSITY   (Sweden)

^b STOCKHOLM UNIVERSITY   (Sweden)

^c ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

^d CEA SACLAY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ENERGY BARRIERS; PROTON TRANSFER; RADICAL ENZYMES; WAVE FUNCTIONS;

ELECTRON TRANSITIONS; PHENOLS; PROTONS; REACTION KINETICS; SOLUTIONS; WATER;

HYDROGEN BONDS;

CARBOXYLIC ACID; ENZYME; OXIDIZING AGENT; PHENOL; PHENOL DERIVATIVE; PROTON; RUTHENIUM; WATER;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; COMPLEX FORMATION; CONCERTED ELECTRON PROTON TRANSFER; ELECTRON; ELECTRON TRANSPORT; ENERGY; HYDROGEN BOND; KINETICS; LASER; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; OXIDATION; PH; PROTON COUPLED ELECTRON TRANSFER;

CARBOXYLIC ACIDS; ELECTRONS; HYDROGEN BONDING; HYDROGEN-ION CONCENTRATION; KINETICS; OXIDATION-REDUCTION; PHENOLS; PHOTOLYSIS;

EID: 33749511624     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja063264f     Document Type: Article

References (47)

1. We use the term PCET to denote all regimes of coupling, from sequential electron-proton transfer or vice versa to a concerted reaction. The latter is denoted CEP and is defined as a reaction with a single transition state for the transfer of both the electron and proton.
2. (a) Stubbe, J.; van der Donk, W. A. Chem. Rev. 1998, 98, 705-762.
3. (b) Stubbe, J.; Nocera, D. G.; Yee, C. S.; Chang, C. Y. Chem. Rev. 2003, 103, 2167-2202.
4. (c) Babcock, G. T. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 12971.
5. (d) Aubert, C.; Vos, M. H.; Mathis, P.; Eker, A. P. M.; Brettel, K. Nature 2000, 405, 586.
6. (a) Hoganson, C. W.; Babcock, G. T. Science 1997, 277, 1953-1956.
7. (b) Tommos, C.; Babcock, G. T. Biochim. Biophys. Acta 2000, 1458, 199-219.
8. (c) Rappaport, F.; Lavergne, J. Biochim. Biophys. Acta 2001, 1503, 246-259.
9. (d) Renger, G. Biochim. Biophys. Acta 2004, 1655, 195-204.
10. .+/TyrOH) ≈ 1.44 V. (a) Lind, J.; Shen, X.; Eriksen, T. E.; Merényi, G. J. Am. Chem. Soc. 1990, 112, 479.
11. (b) Dixon, W. T.; Murphy, D. J. Chem. Soc., Faraday Trans. 2 1976, 72, 1221.
12. (a) Cukier, R. I.; Nocera, D. G. Annu. Rev. Phys. Chem. 1998, 49, 337-369.
13. (b) Chang, C. J.; Chang, M. C. Y.; Damrauer, N. H.; Nocera, D. G.; Biochim. Biophys. Acta 2004, 1655, 13-28.
14. (c) Mayer, J. M. Annu. Rev. Phys. Chem. 2004, 55, 363.
15. (d) Hammes-Schiffer, S. Acc. Chem. Res. 2001, 34, 273-281.
16. (e) Hammes-Schiffer, S.; Iordanova, N. Biochim. Biophys. Acta 2004, 1655, 29-36.
17. (f) Carra, C.; Iordanova, N.; Hammes-Schiffer, S. J. Am. Chem. Soc. 2003, 125, 10429.
18. (g) Costentin, C.; Robert, M.; Saveant, J.-M. J. Electroanal. Chem. 2006, 588, 197-206.
19. (h) Haddox, R. M.; Finklea, H. O. J. Electroanal. Chem. 2003, 550-551, 351-358.
20. (a) Sjödin, M.; Styring, S.; Åkermark, B.; Sun, L.; Hammarström, L. J. Am. Chem. Soc. 2000, 122, 3932-3936.
21. (b) Sjödin, M.; Styring, S.; Åkermark, B.; Sun, L.; Hammarström, L. Philos. Trans. R. Soc. London, Ser. B 2002, 357, 1471-1479.
22. Sjödin, M.; Ghanem, R.; Polivka, T.; Pan, J.; Styring, S.; Sun, L.; Sundström, V.; Hammarström, L. Phys. Chem. Chem. Phys. 2004, 6, 4851-4858.
23. - or base forms of the buffer would increase 10-fold for each pH unit, in contrast to the much weaker dependence observed.
24. Marcus, R. A.; Sutin, N. Biochim. Biophys. Acta 1985, 811, 265-322.
25. As we noted in ref 6 the temperature-dependence of ΔG°′, which arises due to the reaction entropy involved with proton release to the bulk, was not considered in the evaluation of λ. This resulted in a larger (apparent) value, λ = 2.0 eV, as compared to the value later reported in ref 7, λ = 1.4 eV when the temperature-dependence of ΔG°′ had been estimated.
26. For example, see: (a) Thomas, F.; Jarjayes, O.; Jamet, H.; Hamman, S.; Saint-Aman, E.; Duboc, C.; Pierre, J.-L. Angew. Chem., Int. Ed. 2004, 43, 594-597.
27. (b) Maki, T.; Araki, Y.; Ishida, Y.; Onomura, O.; Matsumura, Y. J. Am. Chem. Soc. 2001, 123, 3371-3372.
28. (c) Benisvy, L.; Bittl, R.; Bothe, E.; Garner, C. D.; McMaster, J.; Ross, S.; Teutloff, C.; Neese, F. Angew. Chem., Int. Ed. 2005, 44, 5314-5317.
29. (d) Lachuad, F.; Quaranta, A.; Pellegrin, Y.; Dorlet, P.; Charlot, M.-F.; Un, S.; Leibl, W.; Aukauloo, A. Angew. Chem., Int. Ed. 2005, 44, 1536-1540.
30. (e) Dai, Q.-H.; Tommos, C.; Fuentes, E. J.; Blomberg, M. R. A.; Dutton, P. L.; Wand, A. J. J. Am. Chem. Soc. 2002, 124, 10952-10953.
31. (f) Hay, S.; Westerlund, K.; Tommos, C. Biochemistry 2005, 44, 11891-11902.
32. (a) Biczok, L.; Gupta, N.; Linschitz, H. J. Am. Chem. Soc. 1997, 119, 12601-12609.
33. (b) Sun, L.; Burkitt, M.; Tamm, M.; Raymond, M. K.; Abrahamsson, M.; LeGourriérec, D.; Frapart, Y.; Magnuson, A.; Brandt, P.; Tran, A.; Hammarström, L.; Styring, S.; Åkermark, B. J. Am. Chem. Soc. 1999, 121, 6834-6842.
34. (c) Biczok, L.; Linschitz, H. J. Phys. Chem. A 2001, 105, 11051-11056.
35. (d) Rhile, I. J.; Mayer, J. M. J. Am. Chem. Soc. 2004, 126, 12718-12719.
36. (e) Rhile, I. J.; Markle, T. F.; Nagao, H.; DiPasquale, A. G.; Lam, O. P.; Lockwood, M. A.; Rotter, K.; Mayer, J. M. J. Am. Chem. Soc. 2006, 128, 6075-6088.
37. (f) Costentin, C.; Robert, M.; Savéant, J.-M. J. Am. Chem. Soc. 2006, 128, 4552-4553.
38. (a) Magnuson, A.; Berglund, H.; Korall, P.; Hammarström, L.; Åkermark, B.; Styring, S.; Sun, L. J. Am. Chem. Soc. 1997, 119, 10720.
39. (b) Chang, I. J.; Gray, H. B.; Winkler, J. R. J. Am. Chem. Soc. 1991, 113, 7056.
40. Sjödin, M.; Styring, S.; Wolpher, H.; Xu, Y.; Sun, L.; Hammarström, L. J. Am. Chem. Soc. 2005, 127, 3855-3863.
41. Serjeant, E. P.; Dempsey, B. Ionisation Constants of Organic Acids in Aqueous Solution; Pergamon Press: Oxford, 1970.
42. Mock, W. L.; Morsch, L. A. Tetrahedron 2001, 57, 2957-2964 and references therein.
43. As a control, in response to a reviewers' request, we compared the reaction rates of the hydrogen-bonded systems 1a and 2a at pH = 7 in both 10 and 100 mM buffer and observed no significant difference.
44. 3.
45. Compare with the proton transfer theory of Hynes and co-workers in: (a) Kiefer, P. M.; Hynes, J. T. Solid State Ionics 2004, 168, 219-224 and references therein.
46. (a) Eigen, M. Angew. Chem., Int. Ed. Engl. 1964, 3, 1-72.
47. (b) Gutman, M.; Nachliel, E. Biochim. Biophys. Acta 1990, 1015, 391-414.