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.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
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).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1349–1353, October, 1974.
Rights and permissions
About this article
Cite this article
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
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00470158