Abstract
A comparative study of the kinetics of the N oxidation of 19 derivatives of the pyridine series with perbenzoic acid in chloroform and aqueous dioxane at 20, 25, 30, and 35 °C was made. The rate constants, the parameters of the Arrhenius equation, and the activation energies of the N oxidation of the indicated monoazines were determined. The scale of the reactivities of the derivatives of the pyridine series was calculated within the framework of the Pearson hard-soft acid-base concept.
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Literature cited
E. Ochiai, Aromatic Amino Oxides, Amsterdam (1967), p. 19.
A. R. Katritzky and I. M. Lagowsky, Chemistry of the Heterocyclic X-Oxides, Vol. 3, Academic Press, New York (1971), p. 99.
R. A. Abramovitch, in: Pyridine and Its Derivatives, Supplement, Part 2, New York (1974).
Zh. I. Aksel'rod and V. M. Berezovskii, Usp. Khim.,33, 1337 (1970).
G. A. Tolstikov, Hydroperoxide Oxidation Reactions [in Russian], Nauka, Moscow (1976), p. 149.
G. Modena and P. E. Todesco, Gaz. Chim. Ital.,90, 703 (1960).
A. Dondoni, G. Modena, and P. E. Todesco, Gaz. Chim. Ital.,91, 613 (1961).
A. Dondoni and B. Todesco, Boll. Sci. Fac. Chim. Ind. Bologna,20, 79 (1962).
G. Klopman (ed.), Chemical Reactivity and Reaction Paths, Wiley (1974).
G. Klopman, J. Am. Chem. Soc.,90, 223 (1968).
V. A. Pal'm, Fundamentals of the Quantitative Theory of Organic Reactions [in Russian], Khimiya, Leningrad (1977), p. 289.
A. Gordon and R. Ford, Chemist's Companion: A Handbook of Practical Data, Techniques, and References, Wiley (1973).
G. Klopman, J. Am. Chem. Soc.,86, 4550 (1964).
G. Klopman, J. Am. Chem. Soc.,87, 3300 (1965).
V. N. Kondrat'ev (ed.), Energies Required to Cleave Chemical Bonds, Ionization Potentials, and Electron Affinities [in Russian], Nauka, Moscow (1974).
A. A. Mashkovskii and S. E. Odinokov, Dokl. Akad. Nauk SSSR,204, 1165 (1972).
C. D. Nenitzescu, Organic Chemistry [Russian translation], IL, Vol. 1 (1962), p. 145.
A. Albert, in: Physical Methods in the Chemistry of Heterocyclic Compounds, A. R. Katritsky (ed.), Khimiya, Moscow-Leningrad (1966), p. 15.
N. N. Grandbert, G. K. Fanzova, and A. N. Kost, Khim. Geterotsikl. Soedin., No. 4, 561 (1966).
V. G. Dryuk, M. S. Malinovskii, S. P. Shamrovskaya, S. A. Vasil'chenko, and S. A. Maslov, Zh. Org. Khim.,9, 1228 (1973).
V. L. Antonovskii, Organic Peroxide Initiators, Khimiya, Moscow (1972), p. 352.
V. M. Nabivach and L. A. Venger, Zh. Anal. Khim.,30, 604 (1975).
R. Schreiner and A. Berger, Organic Syntheses [Russian translation], Coll. Vol. 3, IL, Moscow (1952), p. 395.
Weygand, and Hilgetag, Preparative Organic Chemistry, Wiley (1972).
L. C. King and W. B. Brownell, J. Am. Chem. Soc.,72, 2507 (1950).
N. D. Cheronis and T. S. Ma, Organic Functional Group Analysis by Micro-and Semimicro Methods, Wiley (1964).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 354–362, March, 1980.
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Lokhov, R.E. Kinetics of the N oxidation of some compounds of the pyridine series with perbenzoic acid in chloroform and aqueous dioxane. Chem Heterocycl Compd 16, 264–271 (1980). https://doi.org/10.1007/BF02401724
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DOI: https://doi.org/10.1007/BF02401724