Proton or Hydrogen Transfer? Charge Distribution Analysis

Waluk, J.

Artykuł - szczegóły

Tytuł artykułu

Proton or Hydrogen Transfer? Charge Distribution Analysis

Autorzy

Waluk J.

Identyfikatory

Warianty tytułu

Języki publikacji

Abstrakty

The meaning of terms "proton transfer" (PT) and "hydrogen transfer" (HT), commonly encountered in the literature, is not always unambiguous, especially in the case of intramolecular tautomerization processes. Depending on the used criterion, the same reaction may be classified as either PT or HT. Two criteria for distinguishing between PT and HT are discussed: (a) formal translocation of charge; (b) the reaction mechanism, in particular the coupling between the motion of the proton and the electron density redistribution. The analysis is illustrated using the values of ground and excited state partial charges calculated for three well-known examples of molecules that undergo photo-induced and/or ground state tautomerization: -hydroxyacetophenone, 2,2'-bi pyridyl- 3,3'-diol, and porphycene.

Słowa kluczowe

proton transfer hydrogen transfer charge distribution

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Polish Journal of Chemistry

Rocznik

2008

Tom

Vol. 82, nr 4

Strony

947--962

Opis fizyczny

Bibliogr. 58 poz., rys.

Twórcy

autor

Waluk J.

Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44, 01-224 Warsaw, Poland, waluk@ichf.edu.pl

Bibliografia

1. Hydrogen Transfer Reactions, J.T. Hynes, H.H. Limbach, J. Klinman, R.L. Schowen (Eds.),Wiley-VCH, Weinheim, 2007.
2. Nishiya T., Yamaguchi S., Hirota N., Baba M. and Hanazaki L, J. Phys. Chem., 90, 5730 (1986).
3. Barbara P.F., Walsh P.K. and Brus L.E., J. Phys. Chem., 93,29 (1989).
4. Peteanu L. A. and Mathies R.A., J. Phys. Chem., 96, 6910 (1992).
5. Hammes-Schiffer S., in: Hydrogen Transfer Reactions, J.T. Hynes, H.H. Limbach, J. Klinman, R. Schowen (Eds.), Wiley-VCH, Weinheim, 2007, p. 479.
6. Hodgkiss J.M., Rosenthal J. and Nocera D.G., in: Hydrogen Transfer Reactions, J.T. Hynes,H.H. Limbach, J. Klinman, R. Schowen (Eds.), Wiley-VCH, Weinheim, 2007, p. 503.
7. Lin M.F., Tseng C.M., Lee Y.T., and Ni C.K., J. Chem. Phys., 123, 124303 (2005).
8. Ashfold M.N.R., Cronin B., Devine A.L., Dixon R.N. and Nix M.G.D., Science, 312, 1637 (2006).
9. Nix M.G.D., Devine A.L., Cronin B. and Ashfold M.N.R., Phys. Chem. Chem. Phys., 8,2610 (2006).
10. Sobolewski A.L., Domcke W, Dedonder-Lardeux C. and Jouvet C., Phys. Chem. Chem. Phys., 2, 1093 (2002).
11. Lan Z., Domcke W, Vallet V, Sobolewski A.L and Mahapatra S., J. Chem. Phys., 122,224315 (2005).
12. Vallet V., Lan Z., Mahapatra S., Sobolewski A.L. and Domcke W, J. Chem. Phys., 123,144307 (2005).
13. Barone V. and Adamo C., Chem. Phys. Lett., 241, l (1995).
14. Sobolewski A.L. and Adamowicz L., Chem. Phys. Lett., 252, 33 (1996).
15. Barone V., Palma A. and Sanna N., Chem. Phys. Lett., 381, 451 (2003).
16. Gelabert R., Moreno M. and Lluch J.M., ChemPhysChem, 5, 1372 (2004).
17. Malsch K. and Hohlneicher G, J. Phys. Chem. A, 101, 8409 (1997).
18. Wu Y.D., Chan K.W.K., Vip C.P., Vogel E., Plattner D.A. and Houk K.N., J. Org. Chem., 62, 9240 (1997).
19. Kozlowski RM., Zgierski M.Z. and Baker J., J. Chem. Phys., 109, 5905 (1998).
20. Malsch K., Roeb M., Karuth V. and Hohlneicher G., Chem. Phys., 227, 331 (1998).
21. Hasegawa J.Y, Takata K., Miyahara T., Neya S., Frisch M.J. and Nakatsuji H., J. Phys. Chem. A, 109, 3187(2005).
22. Waluk J., in: Hydrogen-Transfer Reactions, Hynes J.T., Klinman J.P., Limbach H.H., Schowen R.L. (Eds.), Wiley-VCH, Weinheim, 2007, p. 245.
23. Sigfridsson E. and Ryde U., J. Comput. Chem., 19, 377 (1998).
24. Cioslowski J., J. Am. Chem. Soc., 111, 8333 (1989).
25. Reed A., Weinstock R.B. and Weinhold F., J. Chem. Phys., 83, 735 (1985).
26. Fonseca Guerra C., Handgraaf J.W., Baerends E. J. and Bickelhaupt F.M., J. Comput. Chem., 25, 189 (2003).
27. Martin F. and Zipse H., J. Comput. Chem., 26, 97 (2004).
28. Breneman C.M. and Wiberg K.B., J. Comput. Chem., 11, 361 (1990).
29. Frisch M.J. et al, Gaussian 03, Revision B.03., Gaussian Inc., Pittsburgh, PA, 2003.
30. Ahlrichs R., Bar M., Haser M., Horn H. and Kölmel C., Chem. Phys. Lett., 162, 165 (1989).
31. Sobolewski A.L. and Domcke W., Phys. Chem. Chem. Phys., l, 3065 (1999).
32. Bulska H., Chem. Phys. Lett., 98, 398 (1983).
33. Bulska H., Grabowska A. and Grabowski Z.R., J. Lumin., 35, 189 (1986).
34. Kaschke M., Rentsch S. and Opferman J., Laser Chem., 8, 377 (1988).
35. Sepioł J., Grabowska A., Bulska H., Mordziński A., Perez Salgado F. and Rettschnick R.P.H., Chem. Phys. Lett., 163,443 (1989).
36. Grabowska A., Mordziński A., Tamai N. and Yoshihara K., Chem. Phys. Lett., 169, 450 (1990).
37. Langkilde F.W., Mordziński A. and Wilbrandt R., Chem. Phys. Lett., 190, 305 (1992).
38. Zhang H., van der Meulen P. and Glasbeek M., Chem. Phys. Lett., 253, 97 (1996).
39. Glasbeek M., Marks D. and Zhang H., J. Lumin., 72-4, 832 (1997).
40. Marks D., Zhang H., Glasbeek M., Borowicz P. and Grabowska A., Chem. Phys. Lett., 275,370(1997).
41. Borowicz R, Grabowska A., Les A., Kaczmarek L. and Zagrodzki B., Chem. Phys. Lett., 291, 351 (1998).
42. Marks D., Prosposito R, Zhang H. and Glasbeek M., Chem. Phys. Lett., 289, 535 (1998).
43. Marks D., Zhang H. and Glasbeek M., J. Lumin., 76-7, 52 (1998).
44. Prosposito R, Marks D., Zhang H. and Glasbeek M., J. Phys. Chem. A, 102, 8894 (1998).
45. Marks D., Zhang H., Borowicz R, Grabowska A. and Glasbeek M., Chem. Phys. Lett., 309,19(1999).
46. Neuwahl F.Y.R., Foggi P. and Brown R.G., Chem. Phys. Lett., 319, 157 (2000).
47. Glasbeek M., Toele P. and Zhang H., J. Lumin., 94, 623 (2001).
48. Lochbrunner S., Stock K., Schriever C. and Riedle E., in: Femtochemistry and Femtobiology, Martin M.M., Hynes J.T. (Eds.), Elsevier B.Y, Amsterdam, 2004, p. 193.
49. Borowicz R, Les A., Adamowicz L. and Waluk J., Photochem. Photobiol. Sci, 4, 143 (2005).
50. Wehrle B., Limbach H.H., Kocher M., Ermer O. and Vogel E., Angew. Chem., Int. Ed. Engl, 26, 934 (1987).
51. Waluk J., Muller M., Świderek R, Kocher M., Vogel E., Hohlneicher G. and Michl J., J. Am. Chem. Soc., 113,5511(1991).
52. Waluk J. and Vogel E., J. Phys. Chem., 98, 4530 (1994).
53. Sepioł J., Stepanenko V., Vdovin A., Mordziński A., Vogel E. and Waluk J., Chem. Phys. Lett., 296,549 (1998).
54. Gil M., Jasny J., Yogel E. and Waluk J., Chem. Phys. Lett., 323, 534 (2000).
55. Langer U., Hoelger C., Wehrle B., Latanowicz L., Vogel E. and Limbach H.H., J. Phys. Org. Chem., 13, 23 (2000).
56. Piwoński H., Stupperich C., Hartschuh A., Sepioł J., Meixner A. and Waluk J., J. Am. Chem. Soc., 127, 5302 (2005).
57. Waluk J., Acc. Chem. Res., 39, 945 (2006).
58. Gil M. and Waluk J., J. Am. Chem. Soc., 129, 1335 (2007).

Typ dokumentu

Bibliografia

Identyfikator YADDA

bwmeta1.element.baztech-article-BUJ6-0024-0105