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Issue 47, 2013

Controlled tautomerism – switching caused by an “underground” anionic effect

Author affiliations

Abstract

In a previous communication, we demonstrated a conceptual idea for a tautomeric switching system based on implementation of a flexible piperidine unit in 4-(phenyldiazenyl)naphthalen-1-ol (1). The results showed that a directed shift in the position of the tautomeric equilibrium can be achieved through protonation/deprotonation in a number of solvents. However, the effect of the counter ion in the process of protonation was never considered. The crystallographic analysis of protonated cyano and nitro derivatives of 4-(phenyldiazenyl)-2-(piperidin-1-ylmethyl)naphthalen-1-ol have shown an interesting and unexpected feature: the counter ion is captured in the process of protonation and the shift in the position of the tautomeric equilibrium is achieved through a bridged complex formation. To the best of our knowledge this is a rare example when controlled shift in the position of tautomeric equilibrium is achieved through anion complexation. The results from the solid state analyses are confirmed by NMR spectroscopy in solution and by quantum-chemical calculations.

Graphical abstract: Controlled tautomerism – switching caused by an “underground” anionic effect

Supplementary files

Article information


Submitted
24 Sep 2013
Accepted
16 Oct 2013
First published
16 Oct 2013

RSC Adv., 2013,3, 25410-25416
Article type
Paper

Controlled tautomerism – switching caused by an “underground” anionic effect

L. Antonov, V. Deneva, V. Kurteva, D. Nedeltcheva, A. Crochet and K. M. Fromm, RSC Adv., 2013, 3, 25410 DOI: 10.1039/C3RA45326J

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