Abstract
Studies by electron paramagnetic resonance (EPR), differential scanning calorimetry, thermogravimetric analysis, HPLC and NMR showed that radicals produced by thermolysis and photolysis of benzoyl peroxide,t-butyl peroxide and cumene hydroperoxide included inβ-cyclodextrin (β-CD), undergo significant reaction with theβ-CD. The formation ofβ-CD radicals was observed by EPR. Products formed by addition of radicals toβ-CD were also observed. Such host:guest radical reactions explain the reported stabilization of peroxides, found withβ-CD inclusion, as being primarily due to the interruption of chain reactions by trapping of the chain carriers. A small increase in activation barrier for cleavage of the included peroxide inβ-CD was also observed.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Y. Matsui, H. Naruse, K. Mochida and Y. Date:Bull. Chem. Soc. Jpn. 43, 1910 (1970).
Y. Matsui, H. Naruse, K. Mochida and Y. Date:Bull. Chem. Soc. Jpn. 43, 1909 (1970).
J. Szejtli, in:Inclusion Compounds (Eds. J.L. Atwood, J.E.D. Davies and D.D. MacNicol), p. 331. Academic Press (1984).
T. Hoshino, K. Ishida, T. Irie, F. Hirayama and K. Uekama:J. Incl. Phenom. 6, 415 (1988).
V. Ramamurthy, in:Photochemistry in Organized and Constrained Media (Ed. V. Ramamurthy), p. 303. VCH Publishers Inc. (1991).
V. Ramamurthy and D.F. Eaton:Acc. Chem. Res. 21, 300 (1988).
C.J. Abelt, J.S. Lokey and S.H. Smith:Carbohydr. Res. 192, 119 (1989).
C.A. Chesta and D.G. Whitten:J. Am. Chem. Soc. 114, 2188 (1992).
Y.L. Chow, J. Michon, P. Michon, C. Morat and A. Rassat:Tetrahedron Lett. 33, 3315 (1992).
S. Monti, L. Flamigni, A. Martelli and P. Bortolus:J. Phys. Chem. 92, 4447 (1988).
K. Pitchumani, M.C.D. Manickam and C. Srinivasan:Tetrahedron Lett. 32, 2975 (1991).
V.P. Rao, M.B. Zimmt and N.J. Turro:J. Photochem. Photobiol. A: Chem. 60, 335 (1991).
G.D. Reddy, G. Usha, K.V. Ramanathan and V. Ramamurthy:J. Org. Chem. 51, 3085 (1986).
A.M. Aquino, C.J. Abelt, K.L. Berger, S.E. Darragh, S.E. Kelley and M.V. Cossette:J. Am. Chem. Soc. 112, 5819 (1990).
K.L. Berger, A.L. Nemecek and C.J. Abelt:J. Org. Chem. 56, 3514 (1991).
K.I. Priyadarsini, H. Mohan, J.P. Mittal D.M. Guldi and K.-D. Asmus:J. Phys. Chem. 98, 9565 (1994).
T. Osa, A. Ueno, A. Oskakada and M. Nakoji:E. Patent Appl. 0411951A1, (1991).
I. Tabushi, in:Inclusion Compounds (Eds. J.L. Atwood, J.E.D. Davies and D.D. MacNicol), p. 445. Academic Press (1984).
H. Taguchi, N. Kunieda and M. Kinoshita:Makromol. Chem. 184, 925 (1983).
G. Yamauchi and N. Hirota:J. Am. Chem. Soc. 107, 5021 (1985).
H. Misawa, K. Sawabe and S. TakaharaJ. Chem. Soc. Chem. Commun 357 (1988).
K. Nozaki and P.D. Bartlett:J. Am. Chem. Soc. 68, 1686 (1946).
W.A. Pryor and H.T. Bickley:J. Org. Chem. 37, 2885 (1972).
S. Kohata, K. Jyodoi and A. Ohyoshi:Thermochim. Acta 217, 187 (1993).
F. Shaizadeh and W.F. Degroot, in:Thermal Uses and Properties of Carbohydrates and Lignins (Ed. F. Shaizadeh, K.V. Sarkanen and D.A. Tillman), p. 1. Academic Press (1976).
I.A. Zlochower, W.R. Miller and G.K. Fraenkel:J. Chem. Phys. 42, 3339 (1965).
H. Fischer and H. Hefter:Z. Naturforsch 23a, 1763 (1968).
A.L.J. Beckwith and R.O.C. Norman:J. Chem. Soc. (B) 400 (1969).
P.J. Baugh, J.I. Goodall and J. Bardsley:J. Chem. Soc. Perkin Trans. 2,700 (1977).
M.J. Davies and T.F. Slater:Biochem. J. 245, 167 (1987).
M.J. Davies and T.F. Slater:Biochem. J. 240, 789 (1986).
W. Bors, D. Tait, C. Michel, M. Saran and M. Erben-Russ:Isr. J. Chem. 24, 17 (1984).
J. Svejda and D.H. Volman:J. Phys. Chem. 73, 4417 (1969).
T. Komiya, T. Yamada and S. Nara:Agric. Biol. Chem. 40, 1917 (1976).
B.C. Gilbert, D.M. King and C.B. Thomas:J. Chem. Soc. Perkin Trans. 2, 1186 (1981).
K.P. Madden and R.W. Fessenden:J. Am. Chem. Soc. 104, 2578 (1982).
B.C. Gilbert, D.M. King and C.B. Thomas:J. Chem. Soc. Perkin Trans. 2, 675 (1983).
B.C. Gilbert, D.M. King and C.B. Thomas:Carbohydr. Res. 125, 217 (1984).
K.P. Madden and W.A. Bernhard:J. Phys. Chem. 83, 2643 (1979).
K.P. Madden and W.A. Bernhard:J. Phys. Chem. 84, 1712 (1980).
K.P. Madden and W.A. Bernhard:J. Phys. Chem. 72, 31 (1980).
K.P. Madden and W.A. Bernhard:J. Phys. Chem. 86, 4033 (1982).
K. Phelps, M.N. Lehmann and M.G. Bakker: Unpublished results (1995).
L. Krizanovsky and V. Mentlik:J. Therm. Anal. 13, 571 (1978).
A. Szafranek:J. Therm. Anal. 34, 917 (1988).
S. Bulusu, T. Axenrod, B. Liang, Y. He and L. Yuan:Magn. Reson. Chem. 29, 1018 (1991).
G.D. Meginnis, S. Prince and J. Lowrimore:J. Carbohydr. Chem. 5, 83 (1986).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Lehmann, M.N., Bakker, M.G., Patel, H. et al. The effect of inclusion inβ-cyclodextrin on the chemistry of peroxides: Reactions of radicals withβ-cyclodextrin. J Incl Phenom Macrocycl Chem 23, 99–117 (1995). https://doi.org/10.1007/BF00707888
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00707888