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
- Identifiers
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- RERO DOC 322849
- DOI 10.1016/j.dyepig.2018.03.070
- Persistent URL
- https://folia.unifr.ch/unifr/documents/307156
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