Abstract
On the basis of the measured basicity constants of pyrylium and pyridinium salts containing p-aminophenyl substituents it is shown that the positive charge in the pyrylium cation is considerably higher than in the pyridinium cation. The σ constants of the pyrylium and pyridinium substituents, which show that the magnitude of the electronic effect of the pyrylium ring is considerably higher than that of the pyrydinium ring, were calculated. The reaction of the indicated pyrylium salts with some electrophilic and nucleophilic reagents was examined.
Similar content being viewed by others
Literature cited
W. Dilthey and C. Berres, J. Prakt. Chen., 111, 340 (1925).
F. Kŕóhnke and K. Dickore, Ber., 92, 46 (1959).
V. A. Bren', E. I. Malysheva, and V. I. Minkin, Reakts. Sposobn. Org. Soedin., No. 4, 523 (1967).
É. A. Zvezdina, M. P. Zhdanova, V. A. Bren', and G. N. Dorofeenko, Khim. Geterotsikl. Soedin., No. 11, 1461 (1974).
A. T. Balaban, Tetrahedron, 24, 5059 (1968).
G. N. Dorofeenko, É. A. Zvezdina, and V. V. Derbenev, Zh. Org. Khim., 9, 1079 (1973).
V. I. Minkin and V. A. Bren', Reakts. Sposobn. Org. Soedin., No. 4, 112 (1967).
W. Dilthey, G. Frode, H. Koenen, J. Prakt. Chem., 114, 153 (1926).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1025–1028, August, 1976.
Rights and permissions
About this article
Cite this article
Zvezdina, É.A., Derbenev, V.V., Bren, V.A. et al. Basicities and transformations of pyrylium and pyridinium salts containing p-aminophenyl substituents. Chem Heterocycl Compd 12, 847–850 (1976). https://doi.org/10.1007/BF00510097
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00510097