Kinetic study of hydrolysis of benzoates. Part XXIV-variation of the ortho substituent effect with solvent in the alkaline hydrolysis of substituted phenyl benzoates

Journal of Physical Organic Chemistry

Volumn 18, Issue 11, 2005, Pages 1138-1144

  Nummert, Vilve ^a   Piirsalu, Mare ^a   Mäemets, Vahur ^a   Koppel, Ilmar ^a  

^a UNIVERSITY OF TARTU   (Estonia)

Author keywords

Alkaline hydrolysis; Esters; Kinetics; Ortho effects; Phenyl benzoates; Solvent effects; Substituent effects

Indexed keywords

DATA ACQUISITION; ETHANOL; HYDROLYSIS; RATE CONSTANTS; SPECTROPHOTOMETRY;

ALKALINE HYDROLYSIS; KINETICS; ORTHO EFFECTS; PHENYL BENZOATES; SOLVENT EFFECTS; SUBSTITUENT EFFECTS;

ESTERS;

EID: 27144486126     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/poc.967     Document Type: Article

References (36)

1. Nummert V, Piirsalu M, Palm V. Org. React. 1996; 30: 85-94.
2. Nummert V, Piirsalu M. J. Chem. Soc., Perkin Trans. 2 2000; 583-594.
3. Nummert V, Piirsalu M. Org. React. 1997; 31: 101-109.
4. Nummert V, Piirsalu M. Collect. Czech. Chem. Commun. 2003; 67: 1833-1857.
5. Nummert V, Piirsalu M, Lepp M, Mäemets V, Koppel I. Collect. Czech. Chem. Commun. 2005; 70: 198-222.
6. Fujita T, Nishioka T. Prog. Phys. Org. Chem. 1976; 12: 49-89.
7. Koppel IA, Palm VA. In Advances in Linear Free Energy Relationships, Chapman NB, Shorter J (eds). Plenum Press: London, 1972; Chapt. 5, 203.
8. Koppel IA, Palm VA. Org. React. 1971; 8: 291-301.
9. Nummert V, Piirsalu M. Org. React. 1977; 14: 263-279.
10. Püssa TO, Nummert (Maremäe) VM, Palm VA. Org. React. 1972; 9: 697-728.
11. Nummert V, Eek M, Piirsalu M. Org. React. 1981; 18: 363-374.
12. Nummert VM, Piirsalu MV. Org. React. 1975; 11: 899-910.
13. Bauerova I, Ludvig M. Collect. Czech. Chem. Commun. 2000; 65: 1777-1790.
14. Pirinccioglu N, Williams A. J. Chem. Soc. Perkin Trans. 2 1998; 37-40.
15. Uhlmann F, Meyer GM, Loewenthal O, Gilli E. Liebigs Ann. Chem. 1904; 332: 38-81.
16. Correia VR, Cuccovia IM, Chaimovich H. J. Phys. Org. Chem. 1991; 4: 13-18.
17. Auwers K, Walker AJ. Chem. Ber. 1899; 31: 3037-3046.
18. Kirch JF, Clewell W, Simon A. J. Org. Chem. 1968; 33:127-132.
19. Neuvonen H, Neuvonen K, Pasanen P. J. Org. Chem. 2004; 69: 3794-3800.
20. Hübner H. Liebigs Ann. Chem. 1881; 210: 328-396.
21. Taft RW Jr. In Steric Effects in Organic Chemistry, Newman MS (ed). Wiley: New York, 1956; Chapt. 13, 556.
22. Charton M. Prog. Phys. Org. Chem. 1971; 8: 235-317.
23. Charton M. J. Am. Chem. Soc. 1969; 91: 624-628.
24. Böhm S, Fiedler P, Exner O. New J. Chem. 2004; 28: 67-74.
25. Palm VA (ed). Tables of Rate and Equilibrium Constants of Heterolytic Organic Reactions, vol. 5(11). VINITI: Moscow, 1979.
26. Hansch C, Leo A, Taft RW. Chem. Rev. 1991; 91: 165-195.
27. Taft RW Jr, Lewis IC. J. Am. Chem. Soc. 1958; 80: 2436-2443.
28. Taft RW Jr, Ehrenson S, Lewis IC, Glick RE. J. Am. Chem. Soc. 1959; 81: 5352-5361.
29. Nummert VM, Piirsalu MV. Org. React. 1975; 11: 921-932.
30. Koppel IA, Paju AJ. Org. React. 1974; 11: 137-140.
31. Palm VA. Foundations of Quantitative Theory of Organic Reactions (2nd edn). Khimya: Leningrad, 1977; Chapt. 1 (in Russian).
32. Koppel IA, Koppel JB. Org. React. 1984; 21: 98-123.
33. Koppel IA, Koppel JB. Org. React. 1983; 20: 523-546.
34. Palm VA. J. Chem. Inf. Comput. Sci. 1990; 30: 409-412.
35. Exner O. Collect. Czech. Chem. Commun. 1974; 39: 515-527.
36. Ruff F. J. Mol. Struct. 2003; 617: 31-45.