Tautomerism as primary signalling mechanism in metal sensing: the case of amide group

  1. Vera V. DenevaORCID Logo,
  2. Georgi DobrikovORCID Logo,
  3. Aurelien CrochetORCID Logo,
  4. Daniela Nedeltcheva,
  5. Katharina M. FrommORCID Logo and
  6. Liudmil AntonovORCID Logo

Submitting author affiliation: Institute of Organic Chemistry with Centre of Phytochemistry, Sofia, Bulgaria

Beilstein Arch. 2019, 201923. https://doi.org/10.3762/bxiv.2019.23.v1

Published 20 May 2019

  • Preprint


The concept for sensing systems using the tautomerism as elementary signaling process has been further developed by synthesizing a ligand containing 4-(phenyldiazenyl)naphthalene-1-ol as a tautomeric block and an amide group as metal capturing antenna. Although it has been expected, that the intramolecular hydrogen bonding (between the tautomeric hydroxyl group and the nitrogen atom from the amide group), could stabilize the pure enol form in some solvents, the keto tautomer is also observed. This is a result from formation of intramolecular associates in some solvents. Strong bathochromic and hyperchromic effects on the visible spectra accompany the complex 1:1 formation with some alkaline earth metal ions.

Keywords: tautomerism; molecular sensor; azo dye; amide group; sidearm

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When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Deneva, V. V.; Dobrikov, G.; Crochet, A.; Nedeltcheva, D.; Fromm, K. M.; Antonov, L. Beilstein Arch. 2019, 201923. doi:10.3762/bxiv.2019.23.v1

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