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Kinetics of the cleavage of disulfide bond of dithiobisdisulfides of diimidazoles to their parent imidazoles by hydroxide ion have been investigated spectrophotometrically. Rate equation and other observations suggest that the nucleophilic attack of hydroxide ion on one of the sulfur atoms of disulfide bond is a rate limiting step. This process is accompanied by much slower, parallel reaction with water as a nucleophile. Hence the full kinetic equation for nucleophilic cleavage of 2,2 -dithio-diimidazoles in aqueous alkaline solutions is a two-term equation: –(d[RSSR]/dt) = k1[RSSR][OH–] + k2[RSSR][H2O], where k1 > k2. The mechanism of the reaction is proposed.
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Tom
Strony
1487--1494
Opis fizyczny
Bibliogr. 11 poz., rys.
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autor
autor
- Institute of Chemistry, Poznań University of Technology, Piotrowo 3, 60–965 Poznań, Poland, Jan.Kurzawa@put.poznan.pl
Bibliografia
- 1. Balaban I.E. and King H., J. Chem. Soc., 1858 (1927).
- 2. Suszka A., Polish J. Chem., 54, 2289 (1980).
- 3. Freeman R, Keindl M.C., Po H.N., Brinkman E. and Masse J.A., Synthesis, 714 (1989).
- 4. Danehy J.R and Hunter W.H., J. Org. Chem., 32, 2289 (1967); Danehy J.P., ibid., 33, 568 (1968).
- 5. Kice J.L., in "Sulfur in Organic and Inorganic Chemistry", Vol. l, Senning A., Ed., Marcel Dekker, New York,pp. 175-186(1971).
- 6. Kjellin G. and Sandstrom J., Acta Chim. Scand., 23, 2879 (1969).
- 7. Hais I.M. and Macek K., "Paper Chromatography", Academic Press, New York, p. 768 (1963).
- 8. Boltz D.R and Howell J.A., "Colorimetric Determination of Nonmetals", J. Wiley, New York, p. 478 (1978).
- 9. Daron H.H. and. Aull J.L., Microchem. J., 22, 420 (1977).
- 10. Marquardt D.W., J. Soc. Ind. Appl. Math, 11, 431 (1963).
- 11. Stanovik B. and Tisler M., Anal. Biochem., 9, 68 (1964)
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ5-0014-0082