Abstract
Even when α-ketoacids play an important role as a link between the metabolism of carbohydrates and proteins and their solution chemistry should be of general interest, quantitative information regarding positions of acid-base, keto-enol, and hydration-dehydration equilibria established in their dilute aqueous solutions is rather limited. Only properties of pyruvic acid were studied extensively1, but those of α- ketoglutaric acid received only limited attention1c, 2. For the most complex system represented by oxalacetic acid attention was paid predominantly to keto-enol equilibria3 and only recently the role of hydration yielding a geminal diol has been considered1c, 1f, 4.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
K.J. Pedersen, Acta Chem. Scand., 6, 243 (1952).
M. Becker and H. Strehlow, Z. Elektrochem., 64, 813, 818 (1960).
S. Ono, M. Takagi and T. Wasa, Collect. Czechoslov. Chem. Commun., 26, 141 (1961).
M. Eigen, K. Kustin and H. Strehlow, Z. Physikal. Chem., 31, 140 (1962).
H. Strehlow, Z. Elektrochem., 66, 392 (1962).
M. Takagi, S. Ono and T. Wasa, Review of Polarography (Japan), 11, 210 (1963).
M. Becker, Ber. Bunsenges. Phys. Chem., 68, 669 (1964).
V. Gold, G. Socrates and M.R. Crampton, J. Chem. Soc., 5888 (1964).
V.S. Griffith and G. Socrates, Trans. Faraday Soc., 63, 673 (1967).
G. Öjelund and I. Wadsö, Acta Chem. Scand., 21, 1408 (1967).
Y. Pocker, J.E. Meany, B.J. Nist and C. Zadorojny, J. Phys. Chem., 73, 2879(1969).
Y. Pocker and J.E. Meany, J. Phys. Chem., 74, 1486 (1970).
N. Hellstrom and S.O. Almquist, J. Chem. Soc. B, 1396 (1970).
G.A. Gachko, L.N. Kivach, S.A. Maskevich, Yu.M. Ostrovskii, S.G. Podtynchenko, Dokl. Akad. Nauk BSSR, 27, 946 (1983).
W. Knoche, M.A. Lopez-Quintela and J. Weiffen, Ber. Bunsenges. Phys. Chem., 89, 1047 (1985).
2. J. Jen and W. Knoche, Ber. Bunsenges. Phys. Chem., 72, 539 (1969).
K.H. Meyer, Chem. Ber., 45, 2843 (1912).
A. Hantzsch, Chem. Ber., 48, 1407 (1915).
E. Gelles and R.W. Hay, J. Chem. Soc., 3673 (1958).
B.E.C. Banks, J. Chem. Soc., 5043 (1961).
W.D. Kumler, E. Kun and J.N. Shoolery, J. Org. Chem., 27, 1165 (1962).
G.W. Kosicki, Canad. J. Chem., 40, 1280 (1962).
G.W. Kosicki and S.N. Lilpovac, Canad. J. Chem., 42, 403 (1964).
S.S. Tate, A.K. Grzybowski and S.P. Datta, J. Chem. Soc., 1372 (1964).
C.S. Tsai, Y.T. Lin and E.E. Sharkawi, J. Org. Chem., 37, 85 (1972).
H.L. Hess and R.E. Reed, Arch. Biochem. Biophys., 153, 226 (1972).
D.W. Schiering and J.E. Keaton, J. Molec. Struct., 144, 71 (1986).
C.I. Pogson and R.G. Wolfe, Biochem. Biophys. Res. Commun., 46, 1048 (1972).
F.C. Kokesh, J. Org. Chem., 41, 3593 (1973).
M. Emly and D. Leussing, J. Am. Chem. Soc., 103, 628 (1981).
P.Y. Bruice, J. Am. Chem. Soc., 105, 4982 (1983).
J.P. Segretario, N. Sleszynski, R.E. Partch, P. Zuman and V. Horak, J. Org. Chem., 54, 1986.
For dianioin of oxalacetic acid it has been claimed (Reference 4b) that the relative content of all forms is independent of concentration, but data in Table 3 (Reference 4b) indicate for the content of the hydrated form a significant difference, even when concentration of the acid was changed only from 1.14 M to 1.7 M.
P.Y. Bruice and T.C. Bruice, J. Am. Chem. Soc., 100, 4793 (1978).
P.Y. Bruice and T.C. Bruice, J. Am. Chem. Soc., 100, 4802 (1978).
R. Boyd, “Acidity Functions” in “Solvent-Solute Interactions”, Vol. 1 (J.F. Coetzee and C.D. Ritchie, Eds.), M. Dekker, New York, 1969, p. 97–228.
W.J. Bover and P. Zuman, J. Am. Chem. Soc., 95, 2531 (1973).
T.J.M. Pouw, W.J. Bover and P. Zuman, Advances in Chemistry, 155, 343 (1976).
J. Kozlowski and P. Zuman, J. Am. Chem. Soc., submitted.
E.M. Arnett, Prog. Phys. Org. Chem. (S.G. Cohen, A. Streitwieser, Jr. and R.W. Taft, Eds.), 1, 223–402 (1963).
D. Barnes and P. Zuman, J. Electroanal. Chem., 46, 323 (1973).
P. Zuman, ibid., 75, 523 (1977).
J. Rusling and P. Zuman, ibid., 143, 283 (1983).
K. Vesely and R. Brdicka, Collect. Czechoslov. Chem. Commun., 12, 313 (1947).
R. Bieber and G. Trümpler, Helv. Chim. Acta, 30, 706, 971, 1109, 1286, 1534, 2000 (1947).
P. Valenta, Collect. Czechoslov. Chem. Commun., 25, 853 (1960).
J. Volke and P. Valenta, ibid., 25, 580 (1960).
E. Laviron, Bull. Soc. Chim. Fr., 2325 (1961).
J.P. Segretario, J.F. Rusling and P. Zuman, J. Electroanal. Chem., 143, 291 (1983).
J. Kozlowski and P. Zuman, J. Electroanal. Chem., 226, 69 (1987).
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1988 Plenum Press, New York
About this chapter
Cite this chapter
Kozlowski, J., Zuman, P. (1988). Studies on Acid-Base, Hydration-Dehydration and Keto-Enol Equilibria in Aqueous Solutions of α-Ketoacids by Polarography, Linear Sweep Voltammetry and Spectroscopy. In: Dryhurst, G., Niki, K. (eds) Redox Chemistry and Interfacial Behavior of Biological Molecules. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-9534-2_24
Download citation
DOI: https://doi.org/10.1007/978-1-4615-9534-2_24
Publisher Name: Springer, Boston, MA
Print ISBN: 978-1-4615-9536-6
Online ISBN: 978-1-4615-9534-2
eBook Packages: Springer Book Archive