An activated coumarin-enamine Michael acceptor for CN−

Aaron B. Davis; Rachel E. Lambert; Frank R. Fronczek; Peter J. Cragg; Karl J. Wallace

doi:10.1039/C4NJ00862F

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An activated coumarin-enamine Michael acceptor for CN⁻†

Aaron B. Davis,^a Rachel E. Lambert,^a Frank R. Fronczek,^b Peter J. Cragg^c and Karl J. Wallace*^a

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* Corresponding authors

^a Department of Chemistry and Biochemistry University of Southern Mississippi, Hattiesburg, Mississippi 39406, USA
E-mail: karl.wallace@usm.edu

^b Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana, USA

^c School of Pharmacy and Biomolecular Sciences, University of Brighton, Brighton BN2 4GJ, UK

Abstract

Two coumarin-enamine chemodosimeters have been synthesized in three steps. They have been shown to selectively detect the cyanide ion with a fluorescent response (t_1/2 = 20 s) and a limit of detection approximately 4.2 ppb in DMSO. The X-ray crystal structure of the thermodynamically stable E-(keto) enamine isomer of one compound was obtained and exhibited offset π-stacking.

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Article information

DOI: https://doi.org/10.1039/C4NJ00862F
Article type: Paper
Submitted: 25 May 2014
Accepted: 07 Jul 2014
First published: 08 Jul 2014

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New J. Chem., 2014,38, 4678-4683

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An activated coumarin-enamine Michael acceptor for CN⁻

A. B. Davis, R. E. Lambert, F. R. Fronczek, P. J. Cragg and K. J. Wallace, New J. Chem., 2014, 38, 4678 DOI: 10.1039/C4NJ00862F

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