PCET in the oxidation of ascorbate. Dramatic change of the kinetic isotope effect on the change in solvent polarity

Tetrahedron Letters

Volumn 48, Issue 21, 2007, Pages 3633-3637

  Vuina, Daniela ^a   Pilepić, Viktor ^a   Ljubas, Daniel ^a   Sanković, Krešimir ^a   Sajenko, Ivana ^a   Uršić, Stanko ^a  

^a UNIVERSITY OF ZAGREB   (Croatia)

Author keywords

Ascorbate; Kinetic isotope effects; Proton coupled electron transfer

Indexed keywords

ASCORBIC ACID; ISOTOPE; NITROSOBENZENE; SOLVENT;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION KINETICS; ELECTRON TRANSPORT; ENTHALPY; ENTROPY; MOTION; OXIDATION; THEORETICAL STUDY;

EID: 34247221448     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.03.140     Document Type: Article

References (56)

1. Reece S.Y., Hodgkiss J.M., Stubbe J., and Nocera D.G. Philos. Trans. R. Soc. B 361 (2006) 1351
2. Mayer J.M. Annu. Rev. Phys. Chem. 55 (2004) 363
3. Chang C.J., Chang M.C.Y., Damrauer N.H., and Nocera D.G. Biochim. Biophys. Acta Bioenerg. 1655 (2004) 13
4. Hammes-Schiffer S., and Iordanova N. Biochim. Biophys. Acta Bioenerg. 1655 (2004) 29
5. Cukier R.I. Biochim. Biophys. Acta Bioenerg. 1655 (2004) 37
6. Mayer J.M., and Rhile I.J. Biochim. Biophys. Acta Bioenerg. 1655 (2004) 51
7. Tommos C., and Babcock G.T. Acc. Chem. Res. 31 (1998) 18
8. Dasgupta J., van Willigen R.T., and Dismukes C. Phys. Chem. Chem. Phys. 6 (2004) 4793
9. Mayer J.M., Rhile I.J., Larsen F.B., Mader E.A., Markle T.F., and DiPasquale A.G. Photosynth. Res. 87 (2006) 3
10. Hodgkiss J.M., Damrauer N.H., Pressé S., Rosenthal J., and Nocera D.G. J. Phys. Chem. B 110 (2006) 18853
11. Rosenthal J., Hodgkiss J.M., Young E.R., and Nocera D.G. J. Am. Chem. Soc. 128 (2006) 10474
12. Rhile I.J., Markle T.F., Nagao H., DiPasquale A.G., Lam O.P., Lockwood M.A., Rotter K., and Mayer J.M. J. Am. Chem. Soc. 128 (2006) 6075
13. Sjödin M., Irebo T., Utas J.E., Lind J., Merényi G., Åkermark B., and Hammarström L. J. Am. Chem. Soc. 128 (2006) 13076
14. Li B., Zhao J., Onda K., Jordan K.D., Yang J., and Petek H. Science 311 (2006) 1436
15. Belevich I., Verkhovsky M.I., and Wikström M. Nature 440 (2006) 829
16. Cukier R.I. J. Phys. Chem. 98 (1994) 2377
17. Zhao X.G., and Cukier R.I. J. Phys. Chem. 99 (1995) 945
18. Cukier R.I. J. Phys. Chem. 99 (1995) 16101
19. Cukier R.I. J. Phys. Chem. 100 (1996) 15428
20. Cukier R.I., and Nocera D.G. Annu. Rev. Phys. Chem. 49 (1998) 337
21. Cukier R.I. J. Phys. Chem. B 106 (2002) 1746
22. Soudackov A.V., and Hammes-Schiffer S. J. Chem. Phys. 111 (1999) 4672
23. Soudackov A.V., and Hammes-Schiffer S. J. Chem. Phys. 113 (2000) 2385
24. Decornez H., and Hammes-Schiffer S. J. Phys. Chem. A 104 (2000) 9370
25. Hammes-Schiffer S. Acc. Chem. Res. 34 (2001) 273 and references cited therein
26. Iordanova N., Decornez H., and Hammes-Schiffer S. J. Am. Chem. Soc. 123 (2001) 3723
27. Carra C., Iordanova N., and Hammes-Schiffer S. J. Am. Chem. Soc. 125 (2003) 10429
28. Skone J.H., Soudackov A.V., and Hammes-Schiffer S. J. Am. Chem. Soc. 128 (2006) 16655
29. Hatcher E., Soudackov A.V., and Hammes-Schiffer S. J. Am. Chem. Soc. 129 (2007) 187
30. Hammes-Schiffer S. Acc. Chem. Res. 39 (2006) 93 and references cited therein
31. Pressé S., and Silbey R. J. Chem. Phys. 124 (2006) 164504
32. Singh N., O'Malley P.J., and Popelier P.A. Phys. Chem. Chem. Phys. 7 (2005) 614
33. Macdonald I.K., Badyal S.K., Ghamsari L., Moody P.C.E., and Raven E.L. Biochemistry 45 (2006) 7808
34. Njus D., Wigle M., Kelley P.M., Kipp B.H., and Schlegel H.B. Biochemistry 40 (2001) 11905
35. Njus D., and Kelley P.M. Biochim. Biophys. Acta 1144 (1993) 235
36. Bartlett D., Church D., Bounds P., and Koppenol W.H. Free Radical. Biol. Med. 18 (1995) 85
37. Bisby R.H., and Parker A.W. Arch. Biochem. Biophys. 317 (1995) 170
38. Kytzia A., Korth H.G., Sustmann R., de Groot H., and Kirsch M. Chem. Eur. J. 12 (2006) 8786
39. Uršić S., Vrček V., Ljubas D., and Vinković I. New J. Chem. (1998) 221
40. Mottley C., Kalyanaraman B., and Mason R.P. FEBS Lett. 130 (1981) 12
41. Brezová V., Tarábek P., Dvoranová D., Staško A., and Biskupič S. J. Photochem. Photobiol. A 155 (2003) 179
42. Davies M.B., Austin J., and Partridge D.A. Vitamin C, Its Chemistry and Biochemistry (1991), The Royal Society of Chemistry, Cambridge p 127
43. Bors W., and Buettner G.R. In: Packer L., and Fuchs J. (Eds). Vitamin C in Health and Disease (1997), Marcel Dekker, New York Chapter 4, p 76
44. Kipp B.H., Faraj C., Li G., and Njus D. Bioelectrochemistry 64 (2004) 7
45. Yunes R.A., Terenzani A.J., and do Amaral L. J. Am. Chem. Soc. 97 (1975) 368
46. Eberson L. Electron Transfer Reactions in Organic Chemistry (1987), Springer, New York pp 77-79
47. Romesberg F.E., and Schowen R.L. Adv. Phys. Org. Chem. 39 (2004) 27
48. Kohen A., and Klinman J. Acc. Chem. Res. 31 (2006) 397 and references cited therein
49. Huang H., Sommerfeld D., Dunn B.C., Eyring E.M., and Lloyd C.R. J. Phys. Chem. A 105 (2001) 3536
50. Al-Ajlouni A., Bakac A., and Espenson J.H. Inorg. Chem. 32 (1993) 5792
51. Mayer J.M., Hrovat D.A., Thomas J.L., and Borden W.T. J. Am. Chem. Soc. 124 (2002) 11142
52. DiLabio G.A., and Ingold K.U. J. Am. Chem. Soc. 127 (2005) 6693 and references cited therein
53. Weber M., and Fischer H. J. Am. Chem. Soc. 121 (1999) 7381
54. Jackson R.A., and O'Neill D.W. J. Chem. Soc., Chem. Commun. (1969) 1210
55. Roth J.P., Lowell S., and Mayer J.M. J. Am. Chem. Soc. 122 (2000) 5486 and references cited therein
56. {radical dot}- see Refs. 15a, pp 123-126 and 15b, Chapter 4).