Improved Correlation of 33S Chemical Shifts with pKa's of Arenesulfonic Acids: Use of 33S NMR for pKa Determination

Journal of Organic Chemistry

Volumn 55, Issue 20, 1990, Pages 5494-5496

  French, David C ^a   Crumrine, David S ^a  

^a LOYOLA UNIVERSITY CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0009179340     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00307a021     Document Type: Article

References (20)

1. Cerfontain, H.; Schnitger, B. S. Recl. Trav. Chim. Pays-Bas 1972, 91, 199.
2. Maarsen, P. K.; Bregman, R.; Cerfontain, H. Tetra hedron 1974, 30, 1211.
3. Koeberg-Telder, A.; Cerfontain, H. J. Chem. Soc., Perkin Trans. 2 1975, 226.
4. Hinton, J. F. Annual Reports On NMR Spectroscopy; Webb, G. A,, Ed.; Academic Press: New York, London, 1987; Vol. 19, Chapter 1.
5. Hoffman, R. V.: Belfoure, E. L. J. Am. Chem. Soc. 1982,104, 2183.
6. French, D. C.: Crumrine, D. S. J. Magn. Reson. 1989. 84. 548.
7. Crumrine, D. S.; Shankweiler, J. M.; Hoffman, R. V. J. Org. Chem. 1986, 51, 5013.
8. Hinton, J. F.: Buster, D. J. Magn. Reson. 1984. 57, 494.
9. Cassidei, L.; Sciacovelli, O. J. Magn. Reson. 1985, 62, 529.
10. Crumrine, D. S.; Gillece-Castro, B. J. Org. Chem. 1985, 50, 4408.
11. Farrar, T. C.; Trost, B. M.; Tang, S. L.; Springer-Wilson, S. E. J. Am. Chem. Soc. 1985, 107, 262.
12. O-values for 1, 2, 4, 5-8,10-12, and 15 taken from: Exner, O. Correlation Analysis of Chemical Data; Plenum Press: New York, 1988; p 143.
13. A values for 3, 9,13, and 14 taken from: Exner, O. Correlation Analysis In Chemistry - Recent Advances; Chapman, N. B. Shorter, J., Eds.; Plenum Press: New York, 1978; p 439.
14. March, J. Advanced Organic Chemistry, 3rd ed.; Wiley: New York, 1985; p 221.
15. Drushel, W. A.; Felty, A. R. Am. J. Sci. 1917, 43, 57.
16. Patt, S. L. J. Magn. Reson. 1982, 49, 161.
17. Fukushima, E.; Roeder, S. B. W. J. Magn. Reson. 1979, 33, 199.
18. Seiter, C. H. A.; Feigenson, G. W.; Chan, S. I.; Hsu, M.C. J. Am. Chem. Soc. 1972, 94, 2535.
19. Varian VXR Program temcal(e).
20. a values taken from ref 11a, p 61.