Abstract
The pyridinium ring as a substituent in aniline is an electron acceptor, the effect of which is comparable to the effect of NO2 and N(CH3)2 groups. Correlation of the reactivities with the basicities of the amino groups is not observed in the investigated reactions of N-(aminophenyl)pyridinium perchlorates with some electrophilic reagents, inasmuch as steric factors apparently play a greater role.
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G. N. Dorofeenko, Yu. P. Andreichikov, and G. E. Trukhan, Khim. Geterotsikl. Soedin., 1344 (1974).
C. Toma and A. T. Balaban, Tetrahedron, 22, Suppl. 7, 9 (1966).
A. Camerman, L. H. Jensen, and A. T. Balaban, Acta Cryst., 25, 2632 (1969).
V. A. Bren', B. I. Malysheva, and V. A. Minkin, Reakts. Sposobnost, Organ. Soedin., 4, 523 (1969).
L. Sobczyk, Bull. Acad. Polon. Sci., 9, No. 4, 237 (1961).
I. M. Kolthoff and M. K. Chantooni, J. Amer. Chem. Soc., 87, 4428 (1965).
G. N. Dorofeenko, É. A. Zvezdina, and V. V. Derbenev, Zh. Organ. Khim., 9, 1079 (1973).
V. I. Minkin and V. A. Bren', Reakts. Sposobnost, Organ. Soedin., 4, 112 (1967).
S. V. Krivun, V. I. Dulenko, L. V. Dulenko, and G. N. Dorofeenko, Dokl. Akad. Nauk SSSR, 166, 359 (1966).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1349–1353, October, 1974.
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Dorofeenko, G.N., Andreichikov, Y.P., Zvezdina, É.A. et al. Properties of the amino group in N-(aminophenyl)pyridinium perchlorates. Chem Heterocycl Compd 10, 1177–1181 (1974). https://doi.org/10.1007/BF00470158
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DOI: https://doi.org/10.1007/BF00470158