Solvent-modulated ground-state rotamerism and tautomerism and excited-state proton-transfer processes in o-Hydrpxynaphthylbenzimidazoles

Journal of Physical Chemistry A

Volumn 113, Issue 1, 2009, Pages 56-67

  Brenlla, Alfonso ^a   Rodríguez Prieto, Flor ^a   Mosquera, Manuel ^a   Ríos, Miguel A ^a   Rodríguez, M Carmen Ríos ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTROSCOPY; ACETONITRILE; ETHANOL; ETHYLENE; ETHYLENE GLYCOL; EXCITED STATES; FLUORESCENCE; GLYCEROL; GROUND STATE; HYDROGEN; PROTONS; SOLVENTS; ULTRAVIOLET SPECTROSCOPY;

AB-INITIO CALCULATIONS; APOLAR SOLVENTS; AQUEOUS SOLUTIONS; BENZIMIDAZOLE; EXCITED-STATE; EXCITED-STATE INTRAMOLECULAR PROTON TRANSFERS; HYDROXYL GROUPS; MONO-CATIONS; NORMAL FORMS; PHENYL RINGS; PHOTOACIDS; PROTONATED; QUANTUM MECHANICALS; ROTAMER; TAUTOMERIC EQUILIBRIUM; TIME-RESOLVED FLUORESCENCE SPECTROSCOPIES; ULTRA FASTS; UV-VIS ABSORPTION SPECTROSCOPIES;

PROTON TRANSFER;

2 (1' HYDROXY 2' NAPHTHYL)BENZIMIDAZOLE; 2 (3' HYDROXY 2' NAPHTHYL)BENZIMIDAZOLE; 2-(1'-HYDROXY-2'-NAPHTHYL)BENZIMIDAZOLE; 2-(3'-HYDROXY-2'-NAPHTHYL)BENZIMIDAZOLE; BENZIMIDAZOLE DERIVATIVE; PROTON; SOLVENT;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; PH; QUANTUM THEORY; SPECTROFLUOROMETRY; STEREOISOMERISM; THERMODYNAMICS;

BENZIMIDAZOLES; HYDROGEN-ION CONCENTRATION; MOLECULAR STRUCTURE; PROTONS; QUANTUM THEORY; SOLVENTS; SPECTROMETRY, FLUORESCENCE; STEREOISOMERISM; THERMODYNAMICS;

EID: 60549088771     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp8076003     Document Type: Article

References (44)

1. Sobolewski, A. L.; Domcke, W. Chem. Phys. Chem. 2006, 7, 561.
2. Meyer, T. J.; Huynh, M. H. V.; Thorp, H. H. Angew. Chem., Int. Ed. 2007, 46, 5284.
3. Hosier, J. P.; Ferguson-Miller, S.; Mills, D. A. Annu. Rev. Biochem. 2006, 75, 165.
4. Hydrogen-Transfer Reactions; Hynes, J. T., Klinman, J. P., Limbach, H. H., Schowen, R. L., Eds.; 2007; Vol. 1-4.
5. Formosinho, S. J.; Arnaut, L. G. J. Photochem. Photobiol, A 1993, 75, 21.
6. Ormson, S. M.; Brown, R. G. Prog. React. Kinet. 1994, 19, 45.
7. Chen, K.-Y.; Hsieh, C.-C.; Cheng, Y.-M.; Lai, C.-H.; Chou, P.-T. Chem. Commun. 2006, 4395.
8. Park, S.; Kwon, O.-H.; Kim, S.; Park, S.; Choi, M.-G.; Cha, M.; Park, S. Y.; Jang, D.-J. J Am. Chem. Soc. 2005, 127, 10070.
9. Paterson, M. J.; Robb, M. A.; Blancafort, L.; DeBellis, A. D. J Phys. Chem. A 2005, 109, 7527.
10. Klymchenko, A. S.; Stoeckel, H.; Takeda, K.; Mely, Y. J. Phys. Chem. B 2006, 110, 13624.
11. Rodembusch, F. S.; Leusin, F. P.; da Costa Medina, L. F.; Brandelli, A.; Stefani, V. Photochem. Photobiol. Sci. 2005, 4, 254.
12. Yushchenko, D. A.; Shvadchak, V. V.; Klymchenko, A. S.; Duportail, G.; Pivovarenko, V. G.; Mely, Y. J. Phys. Chem. A 2007, 111, 8986.
13. Sobolewski, A. L. Phys. Chem. Chem. Phys. 2008, 10, 1243.
14. Ma, D.; Liang, F.; Wang, L.; Lee, S. T.; Hung, L. S. Chem. Phys. Lett. 2002, 358, 24.
15. Gaenko, A. V.; Devarajan, A.; Tselinskii, I. V.; Ryde, U. J Phys. Chem. A 2006, 110, 7935.
16. Mansueto, E. S.; Wight, C. A. J. Am. Chem. Soc. 1989, 111, 1900.
17. Silvi, S.; Arduini, A.; Pochini, A.; Secchi, A.; Tomasulo, M.; Raymo, F. M.; Baroncini, M.; Credi, A. J. Am. Chem. Soc. 2007, 129, 13378.
18. Gutman, M.; Nachliel, E. Annu. Rev. Phys. Chem. 1997, 48, 329.
19. Agmon, N. J. Phys. Chem. A 2005, 109, 13.
20. Perez-Lustres, J. L.; Rodríguez-Prieto, F.; Mosquera, M.; Senyushkina, T. A.; Ernsting, N. P.; Kovalenko, S.A. J. Am. Chem. Soc. 2007, 129, 5408.
21. Waluk, J. Conformational Analysis of Molecules in Excited States; Wiley-VCH: New York, 2000.
22. Williams, D. L.; Heller, A. J. Phys. Chem. 1970, 74, 4473.
23. Sinha, H. K.; Dogra, S. K. Chem. Phys. 1986, 102, 337.
24. Das, K.; Sarkar, N.; Majumdar, D.; Bhattacharyya, K. Chem. Phys. Lett. 1992, 198, 443.
25. Das, K.; Sarkar, N.; Ghosh, A. K.; Majumdar, D.; Nath, D. N.; Bhattacharyya, K. J. Phys. Chem. 1994, 98, 9126.
26. Douhal, A.; Amat-Guerri, F.; Lillo, M. P.; Acufia, A. U. J. Photochem. Photobiol., A 1994, 78, 127.
27. Mosquera, M.; Penedo, J. C.; Ríos Rodriguez, M. C.; Rodríguez-Prieto, F. J. Phys. Chem. 1996, 100, 5398.
28. Ríos, M. A.; Ríos, M. C. J. Phys. Chem. A 1998, 102, 1560.
29. Ríos Vázquez, S.; Ríos Rodríguez, M. C.; Mosquera, M.; Rodríguez-Prieto, F. J. Phys. Chem. A 2008, 112, 376.
30. Rodríguez Prieto, F.; Ríos Rodríguez, M. C.; Mosquera González, M.; Ríos Fernández, M. A. J. Phys. Chem. 1994, 98, 8666.
31. Mosquera, M.; Ríos Rodríguez, M. C.; Rodríguez- Prieto, F. J. Phys. Chem. A 1997, 101, 2766.
32. Penedo, J. C.; Mosquera, M.; Rodríguez-Prieto, F. J. Phys. Chem. A 2000, 104, 7429.
33. Douhal, A.; Amat-Guerri, F.; Acufña, A. U.; Yoshihara, K. Chem. Phys. Lett. 1994, 217, 619.
34. Hein, D. W.; Alheim, R. J.; Leavitt, J. J. J. Am. Chem. Soc. 1957, 79, 427.
35. Melhuish, W. H. J Phys. Chem. 1961, 65, 229.
36. Crosby, G. A.; Demas, J. N. J. Phys. Chem. 1971, 75, 991.
37. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian '03; Gaussian, Inc.: Wallingford CT, 2004.
38. Jolliffe, I. T. Principal Component Analysis; Springer-Verlag: New York, 1986.
39. Al-Soufi, W.; Novo, M.; Mosquera, M. Appl. Spectrosc. 2001, 55, 630.
40. Katritzky, A. R. Handbook of Heterocyclic Chemistry; Pergamon Press: New York, 1985.
41. Lee, J.; Robinson, G. W.; Webb, S. P.; Philips, L. A.; Clark, J. H. J. Am. Chem. Soc. 1986, 108, 6538.
42. Penedo, J. C.; Ríos Rodríguez, M. C.; García Lema, I.; Pérez Lustres, J. L.; Mosquera, M.; Rodríguez-Prieto, F. J. Phys. Chem. A 2005, 109, 10189.
43. Bräuer, M.; Mosquera, M.; Pérez-Lustres, J. L.; Rodríguez-Prieto, F. J. Phys. Chem. A 1998, 102, 10736.
44. Ríos Rodríguez, M. C.; Rodríguez-Prieto, F.; Mosquera, M. Phys. Chem. Chem. Phys. 1999, 1, 253.