Abstract
Ionising radiations, employed in a broad range of dose-rate, together with a complex non-linear computation of reaction mechanisms, allow the determination of boundary values of rate constants concerning sorbitylfurfural (SF) reactivity towards a wide series of oxidant and/or virtually harmful radicals. SF reacts with some radicals (H, SO4 -·, CO3 -·, Br2 -·, CH3 ·), produced with both pulse and stationary radiolysis in neutral aqueous solution, having electrophilic and/or oxidative behaviour. The rate constants range from diffusional (k = (7–9 ) × 109 M-1 s-1) to relatively low values (k = 2 × 105 M-1 s-1). The possibility to observe these reactions, by means of radiolytical techniques, is heavily influenced by dose-rate. A relation between the radical E NHE 0 and their reactivity with SF is hinted.
REFERENCES
S. S. Emmi, M. D'Angelantonio, G. Poggi, M. Russo, G. Beggiato and B. Larsen, J. Phys. Chem. A 106, 4598 (2002).
M. D'Angelantonio, S. S. Emmi, G. Poggi and G. Beggiato, J. Phys. Chem. A 103, 858 (1999).
N. K. Kochetkov, L. I. Kubrjashov and M. A. Chlenov, Radiation Chemistry of Carbohydrates.Pergamon, New York, NY (1979).
C. von Sonntag, Adv. Carbohydr. Chem. Biochem. 37, 7 (1980).
G. V. Buxton and Q. G. Mulazzani, in: Electron Transfer in Chemistry, V. Balzani (Ed.), p. 503. Wiley-VCH, Weinheim (2001).
J. W. T. Spinks and R. J. Woods (Eds), An Introduction to Radiation Chemistry, 3rd edn. Wiley, New York, NY (1990).
G. V. Buxton, C. L. Greenstock, W. P. Helman and A. B. Ross, J. Phys. Chem. Ref. Data 17, 513 (1988).
P. Zanoli, G. Baggio and R. Poggioli, Agents Actions 12, 4 (1982).
A. Garzia and P. Zanoli, Riv. Farmacol. Ter. XII, 153 (1981).
S. Bader, L. Carinelli, T. Cavalletti, A. L. Giuliani and S. Traniello, Int. J. Cosmet. Sci. 12, 1 (1990).
G. Scott, Chem. Br., 648 (1985).
A. Hutton, G. Roffi and A. Martelli, Quad. Area Ric. Emilia-Romagna 5, 67 (1974).
S. S. Emmi, M. D'Angelantonio, G. Poggi, G. Beggiato, N. Camaioni, A. Geri, A. Martelli, D. Pietropaolo and G. Zotti, Res. Chem. Intermed. 24, 1 (1998).
FACSIMILE for Windows V. 3.0.3. AEA Technology, Didcot (2000).
Q. G. Mulazzani, M. D'Angelantonio, M. Venturi, M. Z. Hoffman and M. A. J. Rodgers, J. Phys. Chem 90, 5347 (1986).
G. Czapski, J. Holman and B. H. J. Bielski, J. Am. Chem. Soc. 116, 11465 (1994).
P.-Y. Jiang, Y. Katsumura, R. Nagaishi, M. Domae, K. Ishikawa, K. Ishigure and Y. Yoshida, J. Chem. Soc. Faraday Trans. 88, 1653 (1992).
M. D'Angelantonio, M. Venturi and Q. G. Mulazzani, Radiat. Phys. Chem. 32, 319 (1988).
T. Logager and K. Sehested, J. Phys. Chem. 97, 6664 (1993).
Y.-N. Lee and S. E. Schwartz, J. Phys. Chem 85, 840(1981).
G. S. Nahor, J. Phys. Chem. 92, 4359 (1988).
K. H. Schmidt, P. Han and D. M. Bartels, J. Phys. Chem. 99, 10530 (1995).
B. Hickel, J. Phys. Chem. 79, 1054 (1975).
J. Rabani, W. A. Mulac and M. S. Matheson, J. Phys. Chem. 81, 99 (1977).
M. Simic, P. Neta and E. Hayon, J. Phys. Chem. 73, 3794 (1969).
L. V. Shastri, L. J. Mittal and J. P. Mittal, Radiat. Phys. Chem. 28, 359 (1986).
S. S. Emmi, G. Beggiato and G. Casalbore-Miceli, Radiat. Phys. Chem. 33, 29 (1989).
B. H. J. Bielski, D. E. Cabelli, R. L. Arudi and A. B. Ross, J. Phys. Chem. Ref. Data 14, 1041 (1985).
A. Sauer, H. Cohen and D. Meyerstein, Inorg. Chem. 27, 4578 (1988).
A. I. Nikolaev, R. L. Safiullin, R. L. Enikeeva and V. D. Komissarov, Khim. Fiz. 11, 69 (1992).
J. Rabani, D. Klug-Roth and A. Henglein, J. Phys. Chem. 78, 2089 (1974).
E. Bothe and D. Schulte-Frohlinde, Z. Naturforsch. 33B, 786 (1978).
B. Maillard, K. U. Ingold and J. C. Scaiano, J. Am. Chem. Soc. 105, 5095 (1983).
Y. Ilan, J. Rabani and A. Henglein, J. Phys. Chem. 80, 1558 (1976).
J. Moening, D. Bahnemann and K. D. Asmus, Chem.-Biol. Interact. 47, 15 (1983).
X. Shen, J. Lind, T. E. Eriksen and G. Merenyi, J. Phys. Chem. 93, 553 (1989).
Origin®, 6.1 v6.1052 (B232). OriginLab, Northampton, MA (2000).
R. E. Huie, L. C. T. Shoute and P. Neta, Int. J. Chem. Kinet. 23, 541 (1991).
P. Neta, R. E. Huie and A. B. Ross, J. Phys. Chem. Ref. Data 17, 1027 (1988).
C. von Sonntag and H.-P. Schuchmann, in: Peroxyl Radicals, Z. B. Alfassi (Ed.), p. 173. Wiley, Chichester (1997).
S. V. Jovanovic, I. Jovanovic and L. Josimovic, J. Am. Chem. Soc. 114, 9018 (1992).
D. E. Cabelli, in: Peroxyl Radicals, Z. B. Alfassi (Ed.), p. 407. Wiley, Chichester (1997).
H. A. Schwartz and R. W. Dodson, J. Phys. Chem. 93, 409 (1989).
J. F. Endicott, in: Concepts of Inorganic Photochemistry, A. W. Adamson and P. D. Fleischauer (Eds), p. 81. Wiley, New York, NY (1985).
J.-G. Fang, M. Lu, Z.-H. Chen, H.-H. Zhu, Y. Li, L. Yang, L.-M. Wu and Z.-L. Liu, Chem. Eur. J. 8, 4191 (2002).
J. S. Wright, E. R. Johnson and G. A. Di Labio, J. Am. Chem. Soc. 123, 1173 (2001).
P. O'Neill, S. Steenken and D. Schulte-Frolinde, J. Phys. Chem. 79, 2773 (1975).
P. Neta, V. Madhavan, H. Zemel and R. W. Fessenden, J. Am. Chem. Soc. 99, 163 (1977).
S. Steenken, C. J. Warren and B. C. Gilbert, J. Chem. Soc. Perkin Trans. 2, 335 (1990).
K. Henbest, P. Douglas, M. S. Garley and A. Mills, J. Photochem. Photobiol. A 80, 299 (1994).
G. R. Dey, D. B. Naik, K. Kishore and P. N. Moorthy, Radiat. Phys. Chem. 43, 365 (1994).
M. W. Wong, A. Pross and L. Radom, J. Am. Chem. Soc. 116, 6284 (1994).
T. Zytowski and H. Fischer, J. Am. Chem. Soc. 118, 437 (1996).
K. Heberger and A. Lopata, J. Org. Chem. 63, 8646 (1998).
J. Grodkowski, P. Neta, C. J. Schlesener and J. K. Kochi, J. Phys. Chem. 89, 4373 (1985).
S. Steenken and P. Neta, J. Am. Chem. Soc. 104, 1244 (1982).
Rights and permissions
About this article
Cite this article
Russo, M., Sgariglia, L., D'Angelantonio, M. et al. The antioxidant reactivity of sorbitylfurfural towards potential harmful radicals, studied by radiation chemistry techniques. Research on Chemical Intermediates 30, 253–267 (2004). https://doi.org/10.1163/1568567041257544
Issue Date:
DOI: https://doi.org/10.1163/1568567041257544