Phenylazophenol-Quinone Phenylhydrazone Tautomerism in Chromogenic Cryptands and Corands with Inward-Facing Phenolic Units and Their Acyclic Analogues

Eddy Chapoteau, Bronislaw P. Czech, Carl R. Gebauer, Anand Kumar, Koonwah Leong, Daniel T. Mytych, Wolodymyr Zazulak, Dhimant H. Desai, Elzbieta Luboch, Jan Krzykawski, Richard A. Bartsch

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35 Scopus citations

Abstract

A series of 4-(4′-nitrophenol)azophenol compounds is prepared in which ether oxygen-containing substituents are attached at the 2- and 6-positions or connect the 2- and 6-positions to incorporate the chromophoric unit into corand or cryptand structures with inward-facing phenolic groups. The phenylazophenol-quinone phenylhydrazone tautomerism of these compounds, as probed by ultraviolet-visible spectroscopy, reveals a pronounced effect of the structure of the ether oxygen-containing substituents or bridging unit upon the tautomeric equilibrium. Chromogenic responses of five cryptands with inward-facing phenolic groups to sodium and potassium ions are determined and compared.

Original languageEnglish (US)
Pages (from-to)2575-2579
Number of pages5
JournalJournal of Organic Chemistry
Volume56
Issue number7
DOIs
StatePublished - Mar 1 1991

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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