Reactions of aliphatic thiyl radicals in the solid state: Photoisomerization of trans-4,5-dihydroxy-1,2-dithiacyclohexane and oxidation of dithiothreitol

Journal of Physical Chemistry A

Volumn 109, Issue 41, 2005, Pages 9241-9248

  Barrón, Lorena B ^a   Waterman, Kenneth C ^b   Offerdahl, Thomas J ^a   Munson, Eric ^a   Schöneich, Christian ^a  

^a UNIVERSITY OF KANSAS   (United States)

^b PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHOTOISOMERIZATION; RADICALS; RESIDUAL MOISTURE; SYNTHETIC PRODUCTS;

ISOMERIZATION; ISOMERS; OXIDATION; PHOTOCHEMICAL REACTIONS; PHOTOLYSIS; REACTION KINETICS; SULFUR; TRANSPORT PROPERTIES;

AROMATIC COMPOUNDS;

4,5 DIHYDROXY 1,2 DITHIACYCLOHEXANE; 4,5-DIHYDROXY-1,2-DITHIACYCLOHEXANE; CYCLOHEXANE DERIVATIVE; DITHIOTHREITOL;

ARTICLE; CHEMISTRY; ISOMERISM; OXIDATION REDUCTION REACTION; PHOTOCHEMISTRY;

CYCLOHEXANES; DITHIOTHREITOL; ISOMERISM; OXIDATION-REDUCTION; PHOTOCHEMISTRY;

EID: 27544432379     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp052011q     Document Type: Article

References (23)

1. Scheffer, J. R. In Organic Solid State Chemistry; Desiraju, G. R., Ed.; Elsevier: Amsterdam, 1987; pp 1-45.
2. McBride, J. M. Acc. Chem. Res. 1983, 16, 304-312.
3. Byrn, S. R.; Pfeiffer, R. R.; Stowell, J. G. Solid-State Chemistry of Drugs; SSCI, Inc.: West Lafayette, IN, 1999.
4. Feng, X. W.; McBride, J. M. J. Am. Chem. Soc. 1990, 112, 6151-6152.
5. Connors, K. A.; Amidon, G. L.; Stella, V. J. Chemical Stability of Pharmaceuticals; John Wiley & Sons: New York, 1986.
6. Von Sonntag, C. In Sulfur-Centered Reactive Intermediates in Chemistry and Biology; Chatgilialoglu, C., Asmus, K.-D., Eds.; NATO ASI Series, Series A: Life Sciences; Plenum Press: New York, 1990; Vol. 197, 359-366.
7. Faucitano, A.; Buttafava, A.; Mariani, M.; Chatgilialoglu, C. ChemPhysChem 2005, 6, 100-1107.
8. Hadley, J. H., Jr.; Gordy, W. Proc. Natl. Acad. Sci. U.S.A. 1974, 71, 3106-3110.
9. Barrón, L. B.; Waterman, K. C.; Filipiak, P.; Hug, G. L.; Nauser, T.; Schöneich, C. J. Phys. Chem. A 2004, 108, 2247-2255.
10. Eisenberg, G. M. Ind. Eng. Chem., Anal. Ed. 1943, 15, 327-328.
11. Tishmack, P. A.; Bugay, D. E.; Byrn, S. R. J. Pharm. Sci. 2003, 92, 441-474.
12. Bugay, D. E. Pharm. Res. 1993, 10, 317-327
13. Harris, R. K. Nuclear Magnetic Resonance Spectroscopy, John Wiley & Sons: New York, 1994; p 260.
14. Guinier, A. X-Ray Diffraction: In Crystals, Imperfect Crystals, and Amorphous Bodies; Dover Publications: New York, 1994; p 254.
15. Zhang, X.; Zhang, N.; Schuchmann, H.-P.; von Sonntag, C. J. Phys. Chem. 1994, 98, 6541-6547.
16. Von Sonntag, C. The Chemical Basis of Radiation Biology; Taylor & Francis: London, 1987.
17. Viskolcz, B.; Lendvay, G.; Körtvélysi, T.; Seres, L. J. Am. Chem. Soc. 1996, 118, 3006-3009.
18. Konya, K. G.; Paul, T.; Lin, S.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 2000, 122, 7518-7527.
19. Lai, M.; Rao, R.; Fang, X.; Schuchmann, H.-P.; von Sonntag, C. J. Am. Chem. Soc. 1997, 119, 5735-5739.
20. Freeman, F.; Angeletakis, C. N. J. Am. Chem. Soc. 1981, 103, 6232-6235.
21. Chatgilialoglu, C. In The Chemistry of Sulphenic Acids and their Derivatives; Patai, S., Ed.; John Wiley & Sons: New York, 1990; pp 549-569.
22. Akhlaq, M. S.; von Sonntag, C. Z. Naturforsch., C: J. Biosci. 1987, 42, 134-140.
23. Hammes-Schiffer, S. Acc. Chem. Res. 2001, 34, 273-281.