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Digitale Medien

Effect of substituents on the properties of 2-(o-hydroxystyryl) benzimidazolium salts (1972)

Beresneva, N. K. ; Zakhs, É. R. ; Éfros, L. S. ; [weitere]

Springer

Chemistry of heterocyclic compounds 8 (1972), S. 620-622

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Details

ISSN: 1573-8353

Quelle: Springer Online Journal Archives 1860-2000

Thema: Chemie und Pharmazie

Notizen: Abstract The results of a calculation of the benzimidazolium cation and its 5(6)-substituted derivatives by the Hückel MO method show that the ±I effects of substituents have a considerably lesser influence on the magnitude of the charge on the C(2) atom than ±M effects. Replacement of C(5) by a positively charged nitrogen atom (imidazo[4,5-c]pyridinium dication) increases the charge on C(2) to the same extent as the introduction of a substituent with a vacant pZ orbital into the 5 position. In accordance with this, the methyl group in the 2 position of the 1,2,3,5-tetramethylimidazolio[4,5-c]pyridinium ion condenses with salicylaldehyde, but the merocyanine cannot be isolated from the 1,3,5-trimethyl-2-(o-hydroxystyryl) imidazolio[4,5-c]pyridinium diperchlorate because of the irreversible degradation of the latter.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1007/BF00488161

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