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A concept for stimulated proton transfer in 1-(phenyldiazenyl)naphthalen-2-ols

  • Hristova, S. Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia, Bulgaria
  • Deneva, Vera V. Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia, Bulgaria
  • Pittelkow, M. University of Copenhagen, Department of Chemistry, Copenhagen, Denmark
  • Crochet, Aurélien University of Fribourg, Department of Chemistry, Fribourg, Switzerland
  • Kamounah, Fadhil S. University of Copenhagen, Department of Chemistry, Copenhagen, Denmark
  • Fromm, Katharina M. University of Fribourg, Department of Chemistry, Fribourg, Switzerland
  • Hansen, P. E. Roskilde University, Department of Science and Environment, Roskilde, Denmark
  • Antonov, Liudmil Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia, Bulgaria
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    2018
Published in:
  • Dyes and Pigments. - 2018, vol. 156, p. 91-99
English A series of aryl azo derivatives of naphthols (1–3) were studied by means of UV–Vis and NMR spectroscopy in different solvents as well as by quantum chemical calculations and X-ray analysis. Previous studies have shown that Sudan I (1) exists as a tautomeric mixture. The effect of the solvents is minimized by the existing intramolecular hydrogen bond. Therefore, the influence on the tautomeric state in structurally modified 1 has been investigated. Structure 2 contains an additional OH- group, which deprotonates easily and affects the position of the tautomeric equilibrium by changing the electronic properties of the substituent. The implementation of a sidearm in 3 creates a condition for competition between the nitrogen from the azo group and from the piperidine unit for the tautomeric proton. In this case the use of acid as a stimulus for controlling the tautomeric process was achieved.
Faculty
Faculté des sciences et de médecine
Department
Département de Chimie
Language
  • English
Classification
Chemistry
License
License undefined
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Persistent URL
https://folia.unifr.ch/unifr/documents/307156
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