Abstract
The electrochemical reduction of 2-substituted 5(6)-benzimidazoles has been studied with the aid of classical polarography and cyclic voltammetry in acetonitrile. The influence of the substituents in position 2 on the magnitudes of the half-wave potentials of the first stage is exerted by induction and resonance mechanisms with approximately the same contributions, and that on the magnitudes of the half-wave potentials of the second stage predominantly by the resonance mechanism. The possibilities of taking the radical-stabilizing factor σ into account in the correlations are discussed. In order to study the 2-substituted 5(6)-nitrobenzimidazole series, their pK a values in acetonitrile have been determined by potentiometric titration.
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Literature cited
T. I. Vakul'skaya, L. I. Larina, O. B. Nefedova, and V. A. Lopyrev, Khim. Geterotsikl. Soedin., No. 4, 523 (1982).
V. A. Popyrev, L. I. Larina, T. N. Rakhmatulina, E. F. Shibanova, T. I. Vakul'skaya, and M. G. Voronkov, Dokl. Akad. Nauk SSSR, 242, 142 (1978).
T. I. Vakul'skaya, L. I. Lapina, O. B. Nefedova, L. P. Petukhov, M. G. Voronkov, and V. A. Lopyrev, Khim. Geterotsikl. Soedin., No. 10, 1398 (1979).
H. P. Aragwal and M. Bhargava, Indian J. Chem., 12, 84 (1974).
I. M. Sosonkin, G. N. Strogov, V. K. Shchel'tsyn, and N. V. Fedyainov, Khim. Geterotsikl. Soedin., No. 4, 530 (1979).
P. Zuman, Substituent Effects in Organic Polarography, Plenum Press, New York (1967).
V. A. Lopyrev, L. I. Larina, T. I. Vakul'skaya, M. F. Larin, O. B. Devedova, E. F. Shibanova, and M. G. Voronkov, Org. Magn. Reson., 15, 219 (1981).
I. B. Afanas'ev, Usp. Khim., 40, 385 (1971).
I. B. Afanas'ev, Zh. Org. Khim., 11, 1145 (1975).
I. B. Afanas'ev, Zh. Org. Khim., 17, 449 (1981).
T. H. Fisher and A. M. Meierhoefer, J. Org. Chem., 43, 224 (1978).
W. J. Leigh, D. R. Arnold, R. W. R. Humphreys, and P. C. Wong, Can. J. Chem., 58, 2537 (1980).
S. Dincturk and R. A. Jackson, J. Chem. Soc., Perkin Trans. II, No. 8, 1127 (1981).
A. Maccol, Nature (London), 163, No. 4135, 178 (1949).
V. A. Lopyrev, L.I. Larina, T. I. Vakul'skaya, and V. A. Bolotin, Manuscript deposited in VINITI, December 13, 1982, No. 9097-82 Dep.
Yu. M. Kargin, V. Z. Latypova, A. I. Arkhinov, R. Kh. Fassakhov, T. A. Eneikina, and G. P. Sharnin, Zh. Obshch. Khim., 50, 2580 (1980).
C. K. Mann, in: The Electrochemistry of Metals in Nonaqueous Solutions [Russian translation], Mir, Moscow (1974), p. 17.
J. M. Kolthoff and M. K. Chantooni, J. Phys. Chem., 70, 856 (1966).
C. G. Swain and E. S. Lupton, J. Am. Chem. Soc., 90, 4328 (1968).
S. Ehrenson, R. T. C. Brownlee, and R. W. Taft, Progr. Phys. Org. Chem., 10, 1 (1973).
I. B. Afanas'ev and V. L. Trojanker, Org. Magn. Reson., 18, 22 (1982).
L. Joseph and A. Albert, J. Heterocycl. Chem., 3, 107 (1966).
S. S. Berg and E. W. Parnell, J. Chem. Soc., No. 12, 5275 (1961).
L. S. Éfros, Zh. Obshch. Khim., 22, 1008 (1952).
D. Harrison, J. T. Ralph, and A. C. Smith, J. Chem. Soc., No. 5, 293 (1963).
W. Ozegowski and D. Krebs, J. Prakt. Chem., 29, 18 (1965).
B. C. Bishop, A. S. Jones, J. C. Tatlow, J. Chem. Soc., 9, 3076 (1964).
D. Harrison and H. W. Jones, J. Chem. Soc., 6, 886 (1969).
G. Holan, E. L. Samnet, B. C. Ennis, and R. W. Hinde, J. Chem. Soc., C, No. 1, 20 (1967).
R. Copeland and A. Day, J. Am. Chem. Soc., 65, 1072 (1943).
K. H. Buchel, Z. Naturforsch., 25b, 945 (1970).
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For communication 3, see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1246–1251, September, 1984.
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Lopyrev, V.A., Larina, L.I., Baumane, L.K. et al. Esr and polarography of nitroazoles. 4. Polarographic study of nitrobenzimidazoles. Chem Heterocycl Compd 20, 1021–1026 (1984). https://doi.org/10.1007/BF00506400
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DOI: https://doi.org/10.1007/BF00506400