Kinetics and mechanism of hydration of o-thioquinone methide in aqueous solution. Rate-determining protonation of sulfur

Journal of Organic Chemistry

Volumn 70, Issue 5, 2005, Pages 1643-1646

  Chiang, Yvonne ^a   Kresge, A Jerry ^a   Sadovski, Oleg ^a   Zhan, Hao Qiang ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CATALYSIS; HEAVY WATER; HYDRATION; INORGANIC ACIDS; KETONES; OXYGEN; SOLUTIONS; SULFUR COMPOUNDS;

FLASH PHOTOLYSIS; PERCHLORIC ACID; PROTON TRANSFER REACTION MECHANISMS; PROTONATION;

REACTION KINETICS;

ACETIC ACID; ISOTOPE; O THIOQUINONE METHIDE; PERCHLORIC ACID; QUINONE DERIVATIVE; SOLVENT; SULFUR; THIOSALICYLIC ACID; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; HYDRATION; MATHEMATICAL ANALYSIS; MATHEMATICAL COMPUTING; PHOTOLYSIS; PROTON TRANSPORT; REACTION ANALYSIS; SYNTHESIS;

ALKENES; KINETICS; MOLECULAR STRUCTURE; PROTONS; QUINONES; SULFUR; WATER;

EID: 14544300967     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0402677     Document Type: Article

References (27)

1. Wan, P.; Barker, B.; Dio, L.; Fischer, M.; Shi, Y.; Yang, C. Can J. Chem. 1996, 24, 465-475. Van De Water, R. W.; Pettus, T. R. R. Tetrahedron 2002, 58, 5367-5405.
2. Wan, P.; Barker, B.; Dio, L.; Fischer, M.; Shi, Y.; Yang, C. Can J. Chem. 1996, 24, 465-475. Van De Water, R. W.; Pettus, T. R. R. Tetrahedron 2002, 58, 5367-5405.
3. Sipila, J.; Brunow, G. Bull. Liaison-Groupe Poyphenols 1992 16, 140-143. Gratz, J. S.; Chen, C. L. In Lignin: Historical, Biological, and Materials Perspectives; Glasser, W. G., Northey, R. A., Schultz, T. P., Eds.; ACS Symposium Series 742; American Chemical Society: Washington, DC, 200; pp 392-421.
4. Sipila, J.; Brunow, G. Bull. Liaison-Groupe Poyphenols 1992 16, 140-143. Gratz, J. S.; Chen, C. L. In Lignin: Historical, Biological, and Materials Perspectives; Glasser, W. G., Northey, R. A., Schultz, T. P., Eds.; ACS Symposium Series 742; American Chemical Society: Washington, DC, 200; pp 392-421.
5. Peter, M. W. Angew. Chem., Int. Ed. Engl. 1989. 28, 555-570. Bolon, J. L.; Pisha, E.; Zhang, F.; Qui, S. Chem. Res. Toxicol. 1998, 11, 1113-1127. Veldhuysen, W. F.; Shallop, A. J.; Jones, R. A.; Rokita, S. E. J. Am. Chem. Soc. 2001, 123, 11126-11132.
6. Peter, M. W. Angew. Chem., Int. Ed. Engl. 1989. 28, 555-570. Bolon, J. L.; Pisha, E.; Zhang, F.; Qui, S. Chem. Res. Toxicol. 1998, 11, 1113-1127. Veldhuysen, W. F.; Shallop, A. J.; Jones, R. A.; Rokita, S. E. J. Am. Chem. Soc. 2001, 123, 11126-11132.
7. Peter, M. W. Angew. Chem., Int. Ed. Engl. 1989. 28, 555-570. Bolon, J. L.; Pisha, E.; Zhang, F.; Qui, S. Chem. Res. Toxicol. 1998, 11, 1113-1127. Veldhuysen, W. F.; Shallop, A. J.; Jones, R. A.; Rokita, S. E. J. Am. Chem. Soc. 2001, 123, 11126-11132.
8. Meier, H.; Mayer, A. Synthesis 1996, 327-329.
9. Schweig, A.; Diehl, F.; Kesper, K.; Meyer, H. J. Mol. Struct. 1989, 198, 307-325.
10. Andraos, J.; Chiang, Y.; Huang, G. C.; Kresge, A. J.; Scaiano, J. J. Am. Chem. Soc. 1993, 115, 10605-10610.
11. Supporting Information; see paragraph at the end of this paper regarding availability.
12. Cox, R. A. Adv. Phys. Org. Chem. 2000, 35, 1-66.
13. Cox, R. A.; Lam, S.-O.; McClelland, R. A.; Tidwell, T. T. J. Chem. Soc., Perkin Trans. 2 1979, 272-275.
14. Bates, R. G. Determination of pH Theory and Practice; Wiley: New York, 1973; p 49.
15. Chiang, Y.; Kresge, A. J.; Zhu, Y. J. Am. Chem. Soc. 2001, 123, 8089-8094
16. Keeffe, J. R.; Kresge, A. J. In Investigation of Rates and Mechanisms of Reactions; Bernasconi, C. F., Ed.; Wiley: New York, 1986; Chapter XI.
17. Kresge, A. J.; More O'Ferrall, R. A.; Powell, M. F. In Isotopes in Organic Chemistry; Buncel, E., Lee, C. C., Eds.; Elsevier: New York, 1987; Chapter 4.
18. Chiang, Y.; Kresge, A. J.; Zhu, Y. J. Am. Chem. Soc. 2002, 124, 717-722.
19. Symbol "l", rather than "φ" with an appropriate subscript and/ or superscript, is commonly used for the fractionation factor of the hydronium ion.
20. Jencks, W. P.; Salvesen, K. J. Am. Chem. Soc. 1971, 93, 4433-4436.
21. Jarret, R. M.; Saunders, M. J. Am. Chem. Soc. 1985, 107, 2648-2654.
22. Chiang, Y., Kresge, A. J.; Zhu, Y. Phys. Chem. Chem. Phys. 2003, 5, 1039-1042. Chang, J. A.; Kresge, A. J.; Zhan, H.-Q.; Zhu, Y. J. Phys. Org. Chem. 2004, 17, 579-585.
23. Chiang, Y., Kresge, A. J.; Zhu, Y. Phys. Chem. Chem. Phys. 2003, 5, 1039-1042. Chang, J. A.; Kresge, A. J.; Zhan, H.-Q.; Zhu, Y. J. Phys. Org. Chem. 2004, 17, 579-585.
24. (a) Kreevoy, M. M.; Sappenfield, D. S.; Schwabacher, W. J. Phys. Chem. 1965, 69, 2287-2291.
25. (b) Eigen, M.; Kruse, W.; Maass, G. Ber. Bunsen-Ges. 1970, 74, 380-385.
26. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165-195.
27. Kaatze, U. J. Chem. Eng. Data 1989, 34, 371-374