Abstract
The carbon-14 kinetic isotope effect for the decarbonylation of lactic acid[1-14C] in sulfuric acid has been measured in the temperature interval of 20–90°C. The experimental values of (k12C/k14C) are compared with the theoretical14C kinetic isotope effect calculated assuming that one carbon-oxygen stretching vibration is lost in the rate-determining step. The discrepancy between experimentally observed temperature dependence of the14C kinetic isotope effect and the theoretical one is explained by the possible side reactions which change the apparent degrees of decarbonylation and isotopic composition of CH3CHOHCOOH[1-14C] used in experiments aiming at the determination of carbon-14 kinetic isotope effect in the decarbonylation process itself.
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V. F. RAAEN, G. A. ROPP, H. P. RAAEN, Carbon-14, McGraw Hill, New York, 1968, p. 53.
M. ZIELIŃSKI, in: Chemistry of Carboxylic Acids and Esters, S. PATAI (Ed.), Interscience Publishers, London, 1969, Chapter 10.
A. FRY, in: Isotope Effects in Chemical Reactions, ACS Monographs, C. J. COLLINS, N. S. BOWMAN (Eds), VNR Co., New York, 1970, Chapter 6.
H. EYRING, F. W. CAGLE, Jr., J. Phys. Chem., 56 (1952) 889.
J. BIGELEISEN, R. H. HASCHEMEYER, M. WOLFSBERG, P. E. YANKWICH, J. Am. Chem. Soc., 84 (1962) 1813.
G. A. ROPP, A. J. WEINBERGER, O. K. NEVILLE, J. Am. Chem. Soc., 73 (1951) 5573.
G. A. ROPP, J. Am. Chem. Soc., 82 (1960) 842.
B. FINGERMAN, R. M. LEMMON, Bio-Organic Chemistry, Quarterly Report, Dec., Jan. and Febr., 1957–1958, UCRL, 8204.
A. FRY, M. CALVIN, J. Phys. Chem., 56 (1952) 897.
G. LAPIDUS, D. BARTON, P. E. YANKWICH, J. Phys. Chem., 70 (1966) 1575; 70 (1966) 3135.
S. Z. ROGINSKY, Theoretical Principles of the Isotopic Methods of Studies of Chemical Reactions, Academy of USSR, Moscow, 1956.
J. F. DUNCAN, G. B. COOK, Isotopes in Chemistry, Oxford University Press, 1968 and Polish Sci. Publ., Warsaw, 1971.
M. E. MAVER, J. Biol. Chem., 32 (1917) 71.
S. W. CLAUSEN, J. Biol. Chem., 52 (1922) 263.
E. RONZONI, Z. WALLEN-LAWRENCE, J. Biol. Chem., 4 (1927) 363.
M. ZIELIŃSKI, Zeszyty Naukowe Uniwersytetu Jagellońskiego (Universitatis Jagellonicae Acta Chimica-Fasciculus), 34 (1991) 227.
M. ZIELIŃSKI, W. TRACZ, data submitted for Polish Patent Letters.
M. ZIELIŃSKI, H. PAPIERNIK-ZIELINSKA, data submitted for Polish Patent Letters.
M. ZIELIŃSKI, 12th Radiochemical Conf. Marinské Lazné, Czechoslovakia, May 1990, and Annual Meeting of the Polish Chem. Soc., Szczecin, September 1990.
I. ZIOTOWSKI, M. ZIELIŃSKI, Nukleonika, 3 (1958) 529.
M. ZIELIŃSKI, Nucl. Appl., 2 (1966) 51.
M. ZIELIŃSKI, Isotope Effects in Chemistry, Polish Sci. Publ., Warsaw, 1979.
J. BIGELEISEN, M. WOLFSBERG, Advances in Chemical Physics, Vol. 1, I. PRIGOGINE (Ed.) 1958, p. 15.
A. I. GEL'BSTEIN, G. G. SHCHEGLOVA, M. I. TEMKIN, Zh. Fiz. Khim., 30 (1956) 2267.
The Merck Index, M. WINDHOLZ (Ed.), Published by Merck and Co., Inc., Rahway, N. J., 9th ed., 1976, p. 701. (Nos 5187, 5188).
M. ZIELIŃSKI, G. CZARNOTA, H. PAPIERNIK-ZIELIŃSKA, J. Radioanal. Nucl. Chem., 159 (1992) 305.
M. ZIELIŃSKI, H. PAPIERNIK-ZIELIŃSKA, G. CZARNOTA, to be presented at the Annual Meeting of the Polish Chem. Soc., Bialystok, September 1992.
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Zieliński, M., Papiernik-Zielińska, H. Carbon-14 kinetic isotope effect in the decarbonylation of lactic acid[1-14C]. Journal of Radioanalytical and Nuclear Chemistry, Articles 162, 25–33 (1992). https://doi.org/10.1007/BF02039921
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DOI: https://doi.org/10.1007/BF02039921