Electron transfer across multiple hydrogen bonds: The case of ureapyrimidinedione-substituted vinyl ruthenium and osmium complexes

Journal of the American Chemical Society

Volumn 131, Issue 13, 2009, Pages 4892-4903

  Pichlmaier, Markus ^a,b   Winter, Rainer F ^a,b   Zabel, Manfred ^a,b   Záliš, Stanislav ^a,b  

^a UNIVERSITY OF REGENSBURG   (Germany)

^b J HEYROVSKÝ INSTITUTE OF PHYSICAL CHEMISTRY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

BUILDING BLOCK; CO-GROUP; DICATION; DIMERIC STRUCTURE; ELECTRON TRANSFER; HYDROGEN BONDING MOTIFS; HYDROGEN BONDINGS; IN-PHASE; IR BAND ASSIGNMENTS; NON-POLAR SOLVENTS; OSMIUM COMPLEXES; OUT OF PHASE; QUANTUM CHEMICAL CALCULATIONS; RADICAL CATIONS; REDOX-ACTIVE; SUPPORTING ELECTROLYTE; TWO-ELECTRON OXIDATION;

DYES; ELECTROLYTES; ELECTRON TRANSITIONS; FREE RADICAL REACTIONS; HYDROGEN; METABOLISM; OSMIUM; OXIDATION; QUANTUM CHEMISTRY; REDOX REACTIONS; RUTHENIUM; RUTHENIUM COMPOUNDS; SPECTROELECTROCHEMISTRY; SUPERALLOYS; UREA;

HYDROGEN BONDS;

N 5,5 DIALKYL 4,6 DIOXO 1,4,5,6 TETRAHYDROPYRIMIDIN 2 YL UREA DERIVATIVE; OSMIUM DERIVATIVE; PYRIMIDINE DERIVATIVE; RUTHENIUM DERIVATIVE; UNCLASSIFIED DRUG; UREA DERIVATIVE; VINYL DERIVATIVE; OSMIUM; PYRIMIDINONE DERIVATIVE; RUTHENIUM; SOLVENT; UREA;

ARTICLE; CRYSTAL STRUCTURE; ELECTRON TRANSPORT; HYDROGEN BOND; INFRARED SPECTROSCOPY; OXIDATION REDUCTION REACTION; QUANTUM CHEMISTRY; ULTRAVIOLET SPECTROSCOPY; X RAY CRYSTALLOGRAPHY; ANALOGS AND DERIVATIVES; CHEMISTRY; DIMERIZATION; ELECTROCHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; QUANTUM THEORY; SPECTROPHOTOMETRY; SYNTHESIS;

CRYSTALLOGRAPHY, X-RAY; DIMERIZATION; ELECTROCHEMISTRY; ELECTRON TRANSPORT; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; OSMIUM; OXIDATION-REDUCTION; PYRIMIDINONES; QUANTUM THEORY; RUTHENIUM; SOLVENTS; SPECTROPHOTOMETRY; UREA;

EID: 67749093250     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja809566g     Document Type: Article

References (56)

1. Gray, H. B.; Winkler, J. R. In Electron Transfer in Chemistry and Biology; Balzani, V., Ed.; Wiley-VCH: Weinheim, 2001; Vol. 1, p 3.
2. Antonello, S.; Formaggio, F.; Moretto, A.; Toniolo, C.; Maran, F. J. Am. Chem. Soc. 2003, 125, 2874-2875.
3. Serron, S. A.; Aldridge, W. S., III; Fleming, C. N.; Danell, R. M.; Baik, M.-H.; Sykora, M.; Dattelbaum, D. M.; Meyer, T. J. J. Am. Chem. Soc. 2004, 126, 14506-14514.
4. Kümmerle, R.; Kyritsis, P.; Gaillard, J.; Moulis, J.-M. J. Inorg. Biochem. 2000, 79, 83-91.
5. Stubbe, J.; Nocera, D.; Yee, C. S.; Chang, M. C. Y. Chem. Rev. 2003, 103, 2167-2202.
6. Zhang, C. Biochim. Biopphys. Acta, Bioenerg. 2007, 1767, 493-499.
7. Semin, B. K.; Lovyagina, E. R.; Timofeev, K. N.; Ivanov, I. I.; Rubin, A. B.; Seibert, M. Biochemistry 2005, 44, 9746-9757.
8. Liu, H.; Yamamoto, H; J, Wei; Waldeck, D. H. Langmuir 2003, 19, 2378-2387.
9. Langen, R.; Colo'n, J. L.; Casimiro, D. R.; Karpishin, T. B.; Winkler, J. R.; Gray, H. B. J. Biol. Inorg. Chem. 1996, 1, 221-225.
10. Beijer, F. H.; Sijbesma, R. P.; Kooijman, H.; Spek, A. L.; Meijer, E. W. J. Am. Chem. Soc. 1998, 120, 6761-6769.
11. Sijbesma, R. P.; Meijer, E. W. Chem. Commun. 2003, 5-16.
12. Corbin, P. S.; Zimmerman, S. C. J. Am. Chem. Soc. 1998, 120, 9710- 9711.
13. Schmuck, C.; Wienand, W. Angew. Chem., Int. Ed. 2001, 40, 4363- 4369.
14. Hirschberg, J. H. H. K.; Koevoets, R. A.; Sijbesma, R. P.; Meijer, E. W Chem. Eur. J. 2003, 9, 4222-4231.
15. Binder, W. H.; Zirbs, R. Supramolecular Polymers and Networks with Hydrogen Bonds in the Main- and Side-Chain. In Hydrogen Bonded Polymers; Binder, W., Ed.; SpringerLink: Heidelberg, 2007; Vol. 207, pp 1-78.
16. Va'zquez-Campos, S.; Crego-Calama, M.; Reinhoudt, D. N. Supramol. Chem. 2007, 19, 95-106.
17. Sherrington, D. C.; Taskinen, K. A. Chem. Soc. Rev. 2001, 30, 83- 93.
18. Söntjens, S. H. M.; Sijbesma, R. P.; van der Genderen, M. H. P.; Meijer, E. W. J. Am. Chem. Soc. 2000, 122, 7487-7493.
19. Baruah, P. K.; Gonnade, R.; Phalgune, U. D.; Sanjayan, G. D. J. Org. Chem. 2005, 70, 6461-6467.
20. Zhang, J.; Hoeben, F. J. M.; Pouderoijen, M. J.; Schenning, A. P. H. J.; Meijer, E. W.; De Schryver, F. C.; De Feyter, S. Chem. Eur. J. 2006, 12, 9046-9055.
21. Sa'nchez, L; Sierra, M; MartI'n, N.; Myles, A. J.; Dale, T. J.; Rebek, J., Jr.; Seitz, W.; Guldi, D. M Angew. Chem. 2006, 118, 4753-4757.
22. Segura, M. L; Sa'nchez de Mendoza, J; MartI'n, N.; Guldi, D. M. J. Am. Chem. Soc. 2003, 125, 15093-15100.
23. Sun, H.; Steeb, J.; Kaifer, A. E. J. Am. Chem. Soc. 2006, 128, 2820- 2821.
24. Robin, M. B.; Day, P. Adv. Inorg. Chem. Radiochem. 1967, 10, 247- 422.
25. Maurer, J; Linseis, M; Sarkar, B.; Schwerderski, B.; Niemeyer, M.; Kaim, W.; Za'liš, S; Anson, C.; Zabel, M.; Winter, R. F. J. Am. Chem. Soc. 2008, 130, 259-268.
26. Maurer, J.; Sarkar, B.; Kaim, W.; Winter, R. F.; Za'liš, S. Chem.-Eur. J. 2007, 13, 10257-10272.
27. Maurer, J.; Sarkar, B.; Schwederski, B.; Kaim, W.; Winter, R. F.; Za'liš, S. Organometallics 2006, 25, 3701-3712.
28. Maurer, J.; Sarkar, B.; Zalis, S.; Winter, R. F. J. Solid State Electrochem. 2005, 9, 738-749.
29. Maurer, J.; Linseis, M.; Sarkar, B.; Schwederski, B.; Niemeyer, M.; Kaim, W.; Za'liš, S.; Anson, C.; Zabel, M; Winter, R. F. J. Am. Chem. Soc. 2009, 131, 259-268.
30. Werner, H.; Esteruelas, M. A.; Otto, H. Organometallics 1986, 5, 2295.
31. Huang, D.; Streib, W. E.; Bollinger, J. C.; Caulton, K. G.; Winter, R. F.; Scheiring, T. J. Am. Chem. Soc. 1999, 121, 8087-8097.
32. Jung, S.; Ilg, K.; Brandt, C. D.; Wolf, J.; Werner, H. Eur. J. Inorg. Chem. 2004, 46, 9-480.
33. Alcock, N. W.; Cartwright, J.; Hill, A. F.; Marcellin, M.; Rawles, H. M. J. Chem. Soc., Chem. Commun. 1995, 369-370.
34. Maruyama, Y.; Yamamura, K.; Sagawa, T.; Katayama, H.; Ozawa, F. Organometallics 2000, 19, 1308-1318.
35. Sharif, S.; Denisov, G. S.; Toney, M. D.; Limbach, H.-H. J. Am. Chem. Soc. 2007, 129, 6313-6327.
36. Pe'rez, E. M.; Dryden, D. T. F.; Leigh, D. A.; Teobaldi, G.; Zerbetto, F. J. Am. Chem. Soc. 2004, 126, 12210-12211.
37. Bohne, C.; Ihmels, H.; Waidelich, M.; Yihwa, C. J. Am. Chem. Soc. 2005, 127, 17158-17159.
38. Marcus, Y. Chem. Soc. Rev. 1993, 22, 409-416.
39. Abraham, M. H. Chem. Soc. Rev. 1993, 22, 73-83.
40. Stolov, A. A.; Kamalova, D. I.; Borisover, M. D.; Solomonov, B. N.; Remizov, A. R. Spectrochim. Acta 1994, 50A, 145-150.
41. Rudolph, M.; Feldberg, S. DigiSim3, Version 3.03, Bioanalytical Systems, Inc.:West Lafayette, IN, 1994.
42. The alternative model of two closely spaced one-electron waves is only compatible with a splitting of less than 35 mV between the 0/+ and +/2+ waves and gives a less accurate fit.
43. Baranski, A. S.; Fawcett, W. R.; Gilbert, C. M. Anal. Chem. 1985, 57, 166-170.
44. Barrie're, F.; Geiger, W. E. J. Am. Chem. Soc. 2006, 128, 3980-3989.
45. Glöckle, M.; Kaim, W.; Fiedler, J. Organometallics 1998, 17, 4923- 4925.
46. Sherlock, S. J.; Boyd, D. C.; Moasser, B.; Gladfelter, W. L. Inorg. Chem. 1991, 20, 3626-3632.
47. Ahluwalia, V. K.; Sharma, S.; Kaur, M. Spectrochim. Acta 1989, 45A, 917-927.
48. Lin-Vien, D.; Colthup, N. B.; Fateley, W. G.; Grasselli, J. G. The Handbook of Infrared and Raman Characteristic Frequencies of Organic Molecules; Academic Press: San Diego, 1991.
49. Bressan, M.; Rigo, P. Inorg. Chem. 1975, 14, 2286-2288.
50. Briggs, J. C.; McAuliffe, C. A.; Dyer, G. J. Chem. Soc., Dalton Trans. 1984, 423-427.
51. Hall, M. B.; Niu, S.; Reibenspies, J. H. Polyhedron 1999, 18, 1717- 1724.
52. Rathore, R.; Lindeman, S. V.; Kumar, A. S.; Kochi, J. K. J. Am. Chem. Soc. 1998, 120, 6931-6939.
53. Newton, M. D. Chem. Rev. 1991, 91, 767-792.
54. Atwood, C. G.; Geiger, W. E. J. Am. Chem. Soc. 2000, 122, 5477- 5485.
55. Stoll, M. E.; Lovelace, S. R.; Geiger, W. E.; Schimanke, H.; Hyla- Kryspin, I.; Gleiter, R. J. Am. Chem. Soc. 1999, 121, 9343-9351.
56. Woods, J. E.; Ge, Y.; Smith, D. K. J. Am. Chem. Soc. 2008, 130, 10070-10071.