Thermodynamic origin of the increased rate of hydrolysis of phosphate and phosphorothioate esters in DMSO/water mixtures

Journal of Organic Chemistry

Volumn 71, Issue 19, 2006, Pages 7180-7184

  Sorensen Stowell, Kerensa ^a   Hengge, Alvan C ^a  

^a UTAH STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENTHALPY; ESTERS; HYDROLYSIS; MIXTURES; ORGANIC COMPOUNDS; RATE CONSTANTS; SOLVENTS; THERMODYNAMICS;

HYDROLYSIS REACTIONS; PHOSPHOROTHIOATE ESTERS; POLAR APROTIC SOLVENTS; WATER MIXTURES;

PHOSPHATES;

4 NITROPHENYL PHOSPHATE; 4 NITROPHENYLPHOSPHOROTHIOATE; ACETONITRILE; DIMETHYL SULFOXIDE; ORGANOPHOSPHATE; PHOSPHOROTHIOIC ACID DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG; WATER;

ARTICLE; CALCULATION; CHEMICAL ANALYSIS; CHEMICAL REACTION; ENTHALPY; HYDROLYSIS; ORGANIC CHEMISTRY; THERMODYNAMICS;

DIMETHYL SULFOXIDE; HYDROLYSIS; NITROPHENOLS; ORGANOPHOSPHORUS COMPOUNDS; ORGANOTHIOPHOSPHORUS COMPOUNDS; SOLVENTS; THERMODYNAMICS; WATER;

EID: 33749003453     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060896b     Document Type: Article

References (19)

1. Lad, C.; Williams, N. H.; Wolfenden, R. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 5607-10.
2. Abell, K. W. Y.; Kirby, A. J. Tetrahedron Lett. 1986, 27, 1085-1088.
3. Catrina, I. E.; Hengge, A. C. J. Am. Chem. Soc. 1999, 121, 2156-2163.
4. Grzyska, P. K.; Czyryca, P. G.; Golightly, J.; Small, K.; Larsen, P.; Hoff, R. H.; Hengge, A. C. J. Org. Chem. 2002, 67, 1214-20.
5. Cheng, H.; Nikolic-Hughes, I.; Wang, J. H.; Deng, H.; O'Brien, P. J.; Wu, L.; Zhang, Z. Y.; Herschlag, D.; Callender, R. J. Am. Chem. Soc. 2002, 124, 11295-306.
6. Sorensen-Stowell, K.; Hengge, A. C. J. Org. Chem. 2005, 70, 8303-8.
7. Haberfield, P. J. Phys. Chem. 1983, 87, 1423-1426.
8. Haberfield, P.; Fortier, D. J. Org. Chem. 1983, 48, 4554-4557.
9. Haberfield, P.; Friedman, J.; Pinkston, M. F. J. Am. Chem. Soc. 1972, 94, 71-75.
10. Haberfield, P.; Kivuls, J.; Haddad, M.; Rizzo, T. J. Phys. Chem. 1984, 88, 1913-1916.
11. Haberfield, P.; Nudelman, A.; Bloom, A.; Romm, R.; Ginsberg, H. J. Org. Chem. 1971, 36, 1792-1795.
12. Haberfield, P.; Pessin, J. J. Am. Chem. Soc. 1982, 104, 6191-6194.
13. Grunwald, E.; Baughman, G.; Kohnstam, G. J. Am. Chem. Soc. 1960, 82, 5801-5811.
14. Fuchs, R.; Bear, J. L.; Rodewald, R. F. J. Am. Chem. Soc. 1969, 91, 5797-5800.
15. Criss, C. M. In Physical Organic Chemistry of Organic Solvent Systems; Covington, A. K., Dickinson, T., Eds.; Plenum: New York, 1973; p 23-136.
16. Abell, K. W. Y. Ph.D. Thesis, Cambridge University, 1984.
17. Kirby, A. J.; Varvoglis, A. G. J. Am. Chem. Soc. 1967, 89, 415-423.
18. Hengge, A. C. In Comprehensive Biological Catalysis: A Mechanistic Reference; Sinnott, M., Ed.; Academic Press: San Diego, CA, 1998; Vol. 1, pp 517-542.
19. Thatcher, G. R. J.; Kluger, R. Adv. Phys. Org. Chem. 1989, 25, 99-265.