Collect. Czech. Chem. Commun. 2001, 66, 770-784
https://doi.org/10.1135/cccc20010770

Substituent Effects on the Base-Catalysed Hydrolysis of Phenyl Esters of ortho-Substituted Benzoic Acids

Ingrid Bauerová and Miroslav Ludwig*

Department of Organic Chemistry, Faculty of Chemical Technology, University of Pardubice, Čs. Legií 565, CZ-532 10 Pardubice, Czech Republic

References

1. Watson H. B.: Modern Theories of Organic Chemistry, 2nd ed., p. 241. Oxford University Press, London 1941.
2. Taft R. W.: J. Am. Chem. Soc. 1952, 74, 3120. <https://doi.org/10.1021/ja01132a049>
3. Taft R. W.: J. Am. Chem. Soc. 1953, 75, 4231. <https://doi.org/10.1021/ja01113a027>
4. Bowden K., Manser G. E.: Can. J. Chem. 1968, 46, 2941. <https://doi.org/10.1139/v68-488>
5. Charton M., Charton B. I.: J. Org. Chem. 1978, 43, 1161. <https://doi.org/10.1021/jo00400a030>
6. Charton M.: Prog. Phys. Org. Chem. 1981, 13, 119. <https://doi.org/10.1002/9780470171929.ch3>
7. Mager H., Mager P. P., Barth A.: Tetrahedron 1979, 35, 1953. <https://doi.org/10.1016/0040-4020(79)85053-X>
8. Mager H.: Tetrahedron 1981, 37, 509. <https://doi.org/10.1016/S0040-4020(01)92423-8>
9. Pytela O.: Collect. Czech. Chem. Commun. 1996, 61, 704. <https://doi.org/10.1135/cccc19960704>
10. Pytela O.: Collect. Czech. Chem. Commun. 1995, 60, 1502. <https://doi.org/10.1135/cccc19951502>
11. Pytela O.: Collect. Czech. Chem. Commun. 1996, 61, 1191. <https://doi.org/10.1135/cccc19961191>
12. Bauerová I., Ludwig M.: Collect. Czech. Chem. Commun. 2000, 65, 1777. <https://doi.org/10.1135/cccc20001777>
13. Einhorn A., Hollandt F.: Justus Liebigs Ann. Chem. 1898, 301, 95. <https://doi.org/10.1002/jlac.18983010111>
14. Williams D. L., Ronzio A. R.: J. Org. Chem. 1953, 18, 489. <https://doi.org/10.1021/jo01133a003>
15. Titherley A. W., Stubbs L.: J. Chem. Soc. 1914, 105, 304. <https://doi.org/10.1039/ct9140500299>
16. Kochi J. K.: J. Org. Chem. 1961, 26, 932. <https://doi.org/10.1021/jo01062a071>
17. Crich D., Hwang J.-T.: J. Org. Chem. 1998, 63, 2565.
18. Friedrich S. S., Andrews L. J., Keefer R. M.: J. Org. Chem. 1972, 37, 3007. <https://doi.org/10.1021/jo00984a021>
19. Wiliams F. J., Relles H. M., Donahue P. E., Manello J. S.: J. Org. Chem. 1977, 42, 3425. <https://doi.org/10.1021/jo00441a022>
20. Menger F. M., Smith J. H.: J. Am. Chem. Soc. 1969, 91, 5346. <https://doi.org/10.1021/ja01047a025>
21. Heacock R. A., Hey D. H.: J. Chem. Soc. 1954, 2481. <https://doi.org/10.1039/jr9540002481>
22. Michaelis A., Kerkhof W.: Chem. Ber. 1898, 31, 2173.
23. Singh A., Andrews L. J., Keefer R. M.: J. Am. Chem. Soc. 1962, 84, 1179. <https://doi.org/10.1021/ja00866a024>
24. Hegarty A. F., Bruice T.: J. Am. Chem. Soc. 1970, 92, 6575.
25. Cremin D. J., Hegarty A. F.: Tetrahedron 1977, 33, 1823. <https://doi.org/10.1016/0040-4020(77)84067-2>
26. Exner O.: Correlation Analysis of Chemical Data. Plenum Press, SNTL, Prague 1988.
27. Perrin D. D.: pKA Prediction for Organic Acids and Bases, 1st ed. Chapman & Hall, London–New York 1981.
28. Pytela O.: Collect. Czech. Chem. Commun. 1996, 61, 704. <https://doi.org/10.1135/cccc19960704>
29. Charton M.: J. Am. Chem. Soc. 1975, 97, 3691. <https://doi.org/10.1021/ja00846a022>
30. Charton M.: J. Org. Chem. 1977, 42, 3531. <https://doi.org/10.1021/jo00442a018>
31. Charton M.: J. Org. Chem. 1977, 42, 3535. <https://doi.org/10.1021/jo00442a019>
32. Pytela O., Liška J.: Collect. Czech. Chem. Commun. 1994, 59, 2005. <https://doi.org/10.1135/cccc19942005>
33. Hojo M., Utaka M., Yoshida Z.: Tetrahedron 1971, 27, 2713. <https://doi.org/10.1016/S0040-4020(01)98062-7>
34. Evans D. P., Gordon J. J., Watson H. B.: J. Chem. Soc. 1937, 1430. <https://doi.org/10.1039/jr9370001430>