Lactonization and protonation of gluconic acid: A thermodynamic and kinetic study by potentiometry, NMR and ESI-MS

Journal of Solution Chemistry

Volumn 36, Issue 10, 2007, Pages 1187-1200

  Zhang, Zhicheng ^a,b   Gibson, Paul ^a   Clark, Sue B ^a   Tian, Guoxin ^b   Zanonato, Pier Luigi ^b,c   Rao, Linfeng ^b  

^a WASHINGTON STATE UNIVERSITY   (United States)

^b LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

^c UNIVERSITY OF PADOVA   (Italy)

Author keywords

ESI MS; Gluconic acid; Lactonization; NMR; Protonation

Indexed keywords

EID: 34648837863     PISSN: 00959782     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10953-007-9182-x     Document Type: Article

References (28)

1. Yano, S.: Coordination compounds containing sugars and their derivatives. Coord. Chem. Rev. 92, 113-156 (1988)
2. Whitfield, D.M., Stojkovky, S., Sarka, B.: Metal coordination to carbohydrates. Structures and function. Coord. Chem. Rev. 122, 171-225 (1993)
3. Sawyer, D.T.: Metal-gluconate complexes. Chem. Rev. 64, 633-643 (1964)
4. Carper, W.R., Coffin, D.B.: NMR studies of paramagnetic metal ion interactions with gluconate and 1,5-gluconolactone. Inorg. Chimica Acta 167, 261-264 (1990)
5. Goroux, S., Rubini, P., Henry, B., Aury, S.: Complexes of praseodymium(III) with D-gluconic acid. Polyhedron 19, 1567-1574 (2000)
6. 3+ with glycolate, D-gluconate and α-isosaccharinate in neutral aqueous perchlorate solutions. Radiochim. Acta 91, 599-602 (2003)
7. Warwick, P., Evan, N., Hall, T., Vines, S.: Stability constants of uranium(IV)-α-isosaccharinic acid and gluconic acid complexes. Radiochim. Acta 92, 897-902 (2004)
8. Coccioli, F., Vicedomini, M.: On the protonation of gluconate ions and complex formation with lead(II) in acid solutions. Inorg. Nucl. Chem. 40, 2103-2105 (1978)
9. Motekaitis, R.J., Martell, A.E.: Complexes of aluminum(III) with hydroxy carboxylic acids. Inorg. Chem. 23, 18-23 (1984)
10. Sawyer, D.T., Bagger, J.B.: The lactone-acid-salt equilibria for D-glucono-δ-lactone and the hydrolysis kinetics for this lactone. J. Am. Chem. Soc. 81, 5302-5306 (1959)
11. Combes, C.L., Birch, G.G.: Interaction of D-glucono-1,5-lactone with water. Food Chem. 27, 283-298 (1988)
12. Ekberg, S., Ekberg, C., Albinsson, Y.: Characterization of α-isosaccharinic acid: Lactone and carboxylic conformations. J. Solution Chem. 33, 465-477 (2004)
13. Pecsok, R.L., Sandera, J.: The gluconate complexes. II. The ferric-gluconate system. J. Am. Chem. Soc. 77, 1489-1494 (1955)
14. 15N chemical shift referencing in biomolecular NMR. J. Biomol. NMR 6, 135-140 (1995)
15. Wishart, D.S., Nip, A.M.: Protein chemical shift analysis: a practical guide. Biochem. Cell Biol. 76, 153-163 (1998)
16. Bates, R.G.: Determination of pH Theory and Practice. Wiley, New York (1964)
17. Zanonato, P., Di Bernardo, P., Bismondo, A., Liu, G., Chen, X., Rao, L.: Hydrolysis of uranium(VI) at variable temperatures (10-85∈°C). J. Am. Chem. Soc. 126, 5515-5522 (2004)
18. Rao, L., Srinivasan, T.G., Garnov, A.Y., Zanonato, P., Di Bernardo, P., Bismondo, A.: Hydrolysis of neptunium(V) at variable temperatures (10-85∈°C). Geochim. Cosmochim. Acta 68, 4821-4836 (2004)
19. Gans, P., Sabatini, A., Vacca, A.: Investigation of equilibria in solution. Determination of equilibrium constants with the HYPERQUAD suite of programs. Talanta 43, 1739-1753 (1996)
20. Hoffmann, E.D., Stroobant, V.: Mass Spectrometry, Principles and Applications, 2nd. edn. Willey, New York (2002)
21. Drago, R.S.: Nuclear magnetic resonance spectroscopy-additional principles and applications. In: Physical Methods in Chemistry, pp. 252-309. Saunders, Philadelphia (1977)
22. Frassineti, C., Ghelli, S., Gans, P., Sabatini, A., Moruzzi, M.S., Vacca, A.: Nuclear magnetic resonance as a tool for determining protonation constants of natural polyprotic bases in solution. Anal. Biochem. 231, 374-382 (1995)
23. Anderson, D.E., Lu, J., McIntosh, L. Dahlquist, F.W.: In: Clore, G.M., Gronenborr, A.M. (eds.) NMR of Proteins, 258. CRC, Boca Raton (1993)
24. Cho, H.M., Rai, D., Hess, N.J., Xia, Y., Rao, L.: Acidity and structure of isosaccharinate in aqueous solution: a nuclear magnetic resonance study. J. Solution Chem. 32, 691-702 (2003)
25. Martell, A.E., Smith, R.M.: NIST critically selected stability constants of metal complexes. NIST Standard Reference Database 46 Version 6.0, developed by R.J. Motekaitis and distributed by NIST Standard Reference Data (2001)
26. a values in aqueous solution II. Aliphatic alcohols, thiols, and halogenated carboxylic acids. J. Phys. Chem. A 104, 2402-2409 (2000)
27. Kim, H.I., Johnson, P.V., Beegle, L.W., Beauchamp, J.L., Kanik, I.: Electrospray ionization ion mobility spectrometry of carboxylate anions: ion mobilities and a mass-mobility correlation. J. Phys. Chem. A 109, 7888-7895 (2005)
28. Espenson, J.H.: Reversible and concurrent reactions. In: Speer, J.B., Morriss, J.M. (eds.) Chemical Kinetics and Reaction Mechanism, 2nd edn., pp. 46-69. McGraw-Hill, New York (1995)