Benzoid-quinoid tautomerism of schiff bases and their structural analogs: LIII. Schiff bases derived from 5-hydroxy- and 5-hydroxy-6-nitro-2,3-diphenyl-1-benzofuran-4-carbaldehydes View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2007-04

AUTHORS

E. N. Shepelenko, A. V. Tsukanov, Yu. V. Revinskii, A. D. Dubonosov, V. A. Bren’, V. I. Minkin

ABSTRACT

4-Aryl(alkyl)iminomethyl-5-hydroxy-and 4-aryl(alkyl)iminomethyl-5-hydroxy-6-nitro-2,3-diphenyl-1-benzofurans were synthesized and were shown to exist in solution as equilibrium mixtures of benzoid and quinoid tautomers. The fraction of the quinoid form increases with rise in the solvent polarity and in going from N-aryl to N-alkyl derivatives; introduction of an electron-acceptor substituent (nitro group) into the 6-position of the benzofuran system also favors formation of the quinoid tautomer. Complex formation of alkali and alkaline-earth metal cations with the 5-hydroxy-6-nitro-2,3-diphenyl-1-benzofuran-4-carbaldehyde imine having a benzo-15-crown-5 fragment on the nitrogen atom is accompanied by specific changes in the luminescence spectrum and in the state of tautomeric equilibrium, so that this system may be regarded as tautomeric fluorogenic chemosensor for metal cations. More... »

PAGES

559-563

Identifiers

URI

http://scigraph.springernature.com/pub.10.1134/s1070428007040124

DOI

http://dx.doi.org/10.1134/s1070428007040124

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1000260051


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