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http://dx.doi.org/10.5012/bkcs.2004.25.5.699

Stoichiometric Solvation Effects. Solvolysis of Isopropylsulfonyl Chloride  

Koo, In-Sun (Department of Chemistry Education and Research Institute of Natural Science, Gyeongsang National University)
Yang, Ki-Yull (Department of Chemistry Education and Research Institute of Natural Science, Gyeongsang National University)
Shin, Hyeon-Bae (Department of Chemistry, Dong-A University)
An, Sun-Kyoung (Department of Chemistry, Dong-A University)
Lee, Jong-Pal (Department of Chemistry Education and Research Institute of Natural Science, Gyeongsang National University)
Lee, Ik-Choon (Department of Chemistry, Inha University)
Publication Information
Bulletin of the Korean Chemical Society / v.25, no.5, 2004 , pp. 699-703 More about this Journal
Abstract
Solvolyses of isopropylsulfonyl chloride (IPSC) in water, D_2O,\;CH_3OD$, and in aqueous binary mixtures of acetone, ethanol and methanol are investigated at 25, 35 and 45$^{\circ}C$. The Grunwald-Winstein plot of first-order rate constants for the solvolytic reaction of IPSC with $Y_{Cl}$ (based on 2-adamantyl chloride) shows marked dispersions into three separate lines for three aqueous mixtures with a small slope (m < 0.30). The extended Grunwald-Winstein plots for the solvolysis of IPSC show better correlation. The kinetic solvent isotope effects determined in water and methanol are in consistent with the proposed mechanism of the general base catalyzed and/or $S_AN/S_N2$ reaction mechanism for IPSC solvolyses based on mass law and stoichiometric solvation effect studies.
Keywords
Dispersions; Kinetic solvent isotope effects; Stoichiometric solvation effect;
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1 /
[ Frost, A.;Pearson, R. G. ] / Kinetic and Mechanism
2 Bentley, T. W.; Dau-Schmidt, J.-P.; Llewellyn, G.; Mayr, H. J.Org. Chem. 1992, 57, 2387.   DOI
3 Winstein, S.; Fainberg, A.; Grunwald, E. J. Am. Chem. Soc. 1957,79, 4146.   DOI
4 Kevill, D. N.; Anderson, S. W. J. Org. Chem. 1991, 56, 1845.   DOI
5 Bentley, T. W.; Jones, R. O.; Koo, I. S. J. Chem. Soc., Perkin Trans. 2 1994, 753.
6 Bentley, T. W.; Bowen, C. T.; Morten, D. H.; Schleyer, P. v. R. J.Am. Chem. Soc. 1981, 103, 5466.   DOI
7 Bentley, T. W.; Jones, R. O. J. Chem. Soc.,Perkin Trans. 2 1993, 2351.
8 Lee, I.; Koo, I. S.; Kang, H. K. Bull. Korean Chem. Soc. 1981, 2, 41.   DOI
9 Kevill, D. N.; D'Souza, M. J. Phys. Org. Chem. 2002, 15, 881.   DOI   ScienceOn
10 Bentley, T. W.; Llewellyn, G. Prog. Phys. Org. Chem. 1990, 17, 121.   DOI
11 Kim, W. K.; Lee, I. J. Korean Chem. Soc. 1974, 18, 8.
12 Robertson, R. E.; Laughton, P. M. Can. J. Chem. 1957, 35, 1319.   DOI
13 Bentley, T. W.; Carter, G. E. J. Am. Chem. Soc. 1982, 104, 5741.   DOI
14 Oh, J.; Yang, K.; Koo, I. S.; Lee, I. J. Chem. Res. 1993, 310.
15 Bentley, T. W.; Koo, I. S. J. Chem. Soc., Perkin Trans. 2 1989,1385.
16 Fainberg, A.; Winstein, S. J. Am. Chem. Soc. 1957, 79, 1957.
17 Yoh, S. D.; Tsuno, Y.; Yukawa, Y. J. Korean Chem. Soc. 1984, 28, 433.
18 Ciuffarin, E.; Senatore, L.; Isola, M. J. Chem. Soc. Perkin Trans, 2 1972, 468.
19 Rossall, B.; Robertson, R. E. Can. J. Chem. 1971, 49, 1451.   DOI
20 Ballistreri, F. P.; Cantona, A.; Maccarone, E.; Tomaselli, G. A.; Tripolone, M. J. Chem. Soc. Perkin Trans. 2 1981, 438.
21 Winstein, S.; Grunwald, E. J. Am. Chem. Soc. 1948, 70, 846.   DOI
22 Kevill, D. N. In Advances in Quantitative Structure-Property Relationships; Charton, M., Ed.; JAI Press: Greenwich, CT, 1966;Vol. 1, p 81.
23 Bentley, T. W.; Koo, I. S. J. Chem. Soc. Chem. Commun. 1988, 41.
24 Kivinen, A. Acta Chem. Scand. 1965, 19, 835.
25 Yang, K.; Koo, I. S.; Kang, D. H.; Lee, I. Bull. Korean Chem. Soc. 1994, 15, 419.
26 Bentley, T. W.; Koo, I. S.; Norman, S. J. J. Org. Chem. 1991, 56, 1604.   DOI
27 Lee, I.; Koo, I. S.; Shon, S. C.; Lee, H. H. Bull. Korean Chem.Soc. 1982, 3, 92.
28 Frost, A.; Pearson, R. G. Kinetic and Mechanism, 2nd Ed.; Wiley:New York, 1961; Chap. 7.
29 Yoh, S. D. J. Korean Chem Soc. 1975, 19, 240.
30 Bentley, T. W.; Harris, H. C. J. Chem. Soc. Perkin Trans. 2 1986,619.
31 Koo, I. S.; An, S. K.; Yang, K.; Koh, H. J.; Choi, M. H.; Lee, I.Bull. Korean Chem. Soc. 2001, 22, 419.
32 Winstein, S.; Grunwald, E.; Jones, H. W. J. Am. Chem. Soc. 1951,73, 2700.   DOI
33 Yang, K.; Koo, I. S.; Lee, I. J. Phys. Chem. 1995, 99, 15035.   DOI   ScienceOn
34 Bentley, T. W.; Harris, H. C. J. Org. Chem. 1988, 53, 724.   DOI
35 Koo, I. S.; Yang, K.; Kang, K.; Lee, I. Bull. Korean Chem. Soc. 1998, 19, 968.
36 Koo, I. S.; Yang, K.; Kang, K.; Lee, I.; Bentley, T. W. J. Chem. Soc. Perkin Trans, 2 1998, 1179.
37 Bentley, T. W.; Jones, R. O.; Koo, I. S. J. Chem. Soc. Perkin Trans. 2 1994, 753.
38 Barker, J. W.; Nathan, W. W. J. Chem. Soc. 1936, 236.   DOI
39 Bentley, T. W.; Jones, R. O. J. Chem. Soc. Perkin Trans. 2 1993, 2351.
40 Bentley, T. W.; Harris, H. C.; Koo, I. S. J. Chem. Soc. PerkinTrans. 2 1988, 783.
41 Swain, C. G.; Langsdorf, W. P. J. Am. Chem. Soc. 1951, 73, 2813.   DOI
42 Rogne, O. J. Chem. Soc. (B) 1968, 1294.
43 Koo, I. S.; Lee, J. S.; Yang, K.; Kang, K.; Lee, I. Bull. Korean Chem. Soc.1999, 20, 573.
44 Bentley, T. W.; Carter, G. E.; Harris, H. C. J. Chem. Soc. Perkin Trans. 2 1985, 938.
45 Bentley, T. W.; Jones, R. O.; Koo, I. S. J. Chem. Soc. Perkin Trans. 2 1994, 753.
46 An, S. K.; Yang, J. S.; Cho, J. M.; Yang, K.; Lee, J. P.; Bentley, T. W.; Lee, I. Bull. Korean Chem. Soc. 2002, 23, 419.   DOI
47 Kevill, D. N.; D'Souza, M. J. Chem. Res(s). 1993, 174.
48 Yang, K.; Kang, K. D.; Koo, I. S.; Lee, I.Bull. Korean Chem. Soc. 1997, 18, 1186.
49 Rossel, J. B. J. Chem. Soc. 1963, 5183.   DOI
50 Stangeland, L. J.; Senatore, L.; Ciuffarin, E. J. Chem. Soc. Perkin Trans, 2 1972, 852.
51 Kevill, D. N.; D'Souza, M. J. Chem. Soc., Perkin Trans. 2 1997, 1721.
52 Lee, I.; Rhyu, K. B.; Lee, B. C. J. Korean Chem. Soc. 1979, 23, 277.
53 Hall, H. K. Jr. J. Am. Chem. Soc. 1956, 78, 1450.   DOI