Theoretical study of the substituent effects on the S-H bond dissociation energy and ionization energy of 3-pyridinethiol: Prediction of novel antioxidant

Journal of Physical Chemistry A

Volumn 110, Issue 37, 2006, Pages 10904-10911

  Nam, Pham Cam ^a,b   Nguyen, Minh Tho ^a   Chandra, Asit K ^c  

^a UNIVERSITY OF LEUVEN   (Belgium)

^b THE UNIVERSITY OF DANANG   (Viet Nam)

^c NORTH EASTERN HILL UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIOXIDANT POTENTIALS; BOND DISSOCIATION ENTHALPIES; IONIZATION ENERGY (IE); PROTON AFFINITY;

ANTIOXIDANTS; DISSOCIATION; ENTHALPY; IONIZATION; PROBABILITY DENSITY FUNCTION;

CHEMICAL BONDS;

3 PYRIDINETHIOL; 3-PYRIDINETHIOL; ANTIOXIDANT; FREE RADICAL; HYDROGEN; PYRIDINE DERIVATIVE; SULFUR; THIOL DERIVATIVE;

ARTICLE; CHEMISTRY; HYDROGEN BOND; QUANTUM THEORY; THERMODYNAMICS;

ANTIOXIDANTS; FREE RADICALS; HYDROGEN; HYDROGEN BONDING; PYRIDINES; QUANTUM THEORY; SULFHYDRYL COMPOUNDS; SULFUR; THERMODYNAMICS;

EID: 33749635440     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0630020     Document Type: Article

References (40)

1. Valko, M.; Rhodes, C. J., Moncol J., Izakivic, M.; Mazur, M. Chemico-Biological Interaction 2006, 160, 1.
2. Zhu, Q.; Zhang, X.-M.; Fry, A. J. Polym. Degrad. Stab. 1997, 57, 43.
3. Bordwell, F. G.; Zhang, X. M. Acc. Chem. Res. 1993, 26, 510.
4. Mulder, P.; Korth, H. G.; Ingold, K. U. Helv. Chim. Acta 2005, 88, 370.
5. (a) Wu, Y. D.; Lai, D. K. W. J. Org. Chem. 1996, 61, 7904.
6. (b) Zhang, H. Y.; Sun, Y. M.; Chen, D. Z. Quant. Struct. Act. Relat. 2001, 20, 148.
7. (c) Zhang, H. Y.; Ji, H. F. J. Mol. Struct. (THEOCHEM) 2003, 663, 167.
8. S-centered radicals; Alfassi, Z. B., Ed.; John Wiley: Chichester, U.K., 1999.
9. (b) Sulfur-centered Reactive Intermediates in Chemistry and Biology, Chatgilialoglu, C., Asmus, K.-D., Eds.; Plenum Press: New York, 1990.
10. Karoui, H.; Hogg, N.; Frejaville, C.; Tordo, P.; Kalyanaraman, B. J. Biol. Chem. 1996, 271, 6000.
11. Denisov, E. T.; Khydyakov, I. V. Chem. Rev. 1987, 87, 1313.
12. (a) Mukai, K.; Fukuda, K.; Tajima, K.; Ishizu. K. J. Org. Chem. 1988, 53, 430
13. (b) Nagaoka, S.; Kuranaka, A.; Nagashima, U.; Mukai, K. J. Phys. Chem. 1992, 96, 2754.
14. (a) Pratt, D. A.; DiLabio, G. A.; Brigati, G.; Pedulli, G. F.; Valgimigli, L. J. Am. Chem. Soc. 2001, 123, 4625-4626.
15. (b) Wijtmans, M.; Pratt, D. A.; Brinkhorst, J.; Serwa, R.; Valgimigli, L.; Pedulli, G. F.; Porter, N. J. Org. Chem. 2004, 69, 9215.
16. (c) Wijtmans, M.; Pratt, D. A.; Valgimigli, L.; Dilabio, G. N.; Pedulli, G. F.; Porter, N. Angew. Chem., Int. Ed. 2003, 42, 4370.
17. (a) Scott, G. Atomspheric Oxidation of Polymers; Elservier Applied Science: New-York, 1993; Chapters 4 and 8.
18. (b) Rabek, J. F.; Photostabilization of Polymer, Elservier Applied Science: New York, 1990; pp 114-136.
19. DiLabio, G. A.; Pratt, D. A.; LoFaro, A. D.; Wright, J. S. J. Phys. Chem. A 1999, 103, 1653.
20. (a) Nam, P.-C.; Nguyen, M. T.; Chandra, A. K. J. Phys. Chem. A 2005, 109, 10342.
21. (b) Chandra, A. K.; Uchimaru, T. J. Phys. Chem. A 2000, 104, 9244.
22. Chandra, A. K.; Uchimaru, T. Int. J. Mol. Sci. 2002, 3, 407.
23. Chandra, A. K.; Nam, P.-C.; Nguyen, M. T. J. Phys. Chem. A 2003, 107, 9182.
24. Nam, P.-C.; Nguyen, M. T.; Chandra, A. K. J. Phys. Chem. A 2004, 108, 11362.
25. 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, revision B.03; Gaussian, Inc.: Pittsburgh, PA, 2004.
26. Andersson, M. P.; Uvdal, P. J. Phys. Chem. A 2005, 109, 2937.
27. Bordwell, F. G.; Zhang, X.-M.; Satish, A. V.; Cheng, J.-P. J. Am. Chem. Soc. 1994, 116, 6605.
28. McMilen, D. F.; Golden, D. M. Annu. Rev. Phys. Chem. 1982, 33, 493.
29. Do Couto, P. C.; Cabral, B. J. C.; Simoes, J. A. M. Chem. Phys. Lett. 2006, 421, 504.
30. Handbook of Bond Dissociation Energies in Organic Compounds; Luo, Y.-R., Ed.; CRC Press: London, U.K., 2003.
31. Feng, Y.; Wang, J.-T.; Liu, L.; Guo Q.-X. J. Phys. Org. Chem. 2003, 16, 883.
32. Ji, H. F.; Tang, G. Y.; Zhang, H. Y. Bioorg. Med. Chem. 2005, 13, 1031.
33. Mulder, P.; Mozenson, O.; Lin, S.; Bernardes, C. E. S.; da Piedade, M. E. M.; Santos, A. F. L. O. M.; da Silva, M. A. V. R.; DiLabio, G. A.; Korth, H.-G.; Ingold, K. U. J. Phys. Chem. A (ASAP article, July 2006).
34. Haeberlein, M.; Brinck, T. J. Phys. Chem. 1996, 100, 10116.
35. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165.
36. Curtiss, L. A.; Redfern, P. C.; Raghavachari, K.; Pople, J. A. J. Chem. Phys. 1998, 109, 42.
37. DiLabio, G. A.; Wright, J. S. Chem. Phys. Lett. 1999, 311, 215.
38. DiLabio, G. A.; Pratt, D. A.; Wright, J. S. J. Org. Chem. 2000, 65, 2195.
39. Musialik, M.; Litwinienko, G. Org. Lett. 2005, 7, 4951.
40. Zhang, H. Y.; Ji, H. F. New J. Chem. 2006, 30, 503.