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Tautomerism in azo dyes: Border cases of azo and hydrazo tautomers as possible NMR reference compounds

  • Deneva, Vera Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia, Bulgaria
  • Lyčka, Antonin Faculty of Science, University of Hradec Králové, Czech Republic
  • Hristova, S. Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia, Bulgaria
  • Crochet, Aurélien Department of Chemistry, University of Fribourg, Switzerland
  • Fromm, Katharina M. Department of Chemistry, University of Fribourg, Switzerland
  • Antonov, Liudmil Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia, Bulgaria
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    01.06.2019
Published in:
  • Dyes and Pigments. - 2019, vol. 165, p. 157–163
English In order to meet the need for NMR reference compounds in the study of tautomeric azo dyes, two series of azo dyes, derived from 3-methyl-1-phenyl-4- (phenyldiazenyl)-1H-pyrazol-5-amine and 5-methyl-2-phenyl-4-(2- phenylhydrazono)-2,4-dihydro-3H-pyrazol-3-one, have been studied by using molecular spectroscopy (UV–Vis and NMR) and quantum-chemical calculations (M06- 2X/TZVP) in solution. The results clearly indicate that 3-methyl-1-phenyl-4- (phenyldiazenyl)-1H-pyrazol-5-amines are present in pure azo tautomeric form, while 5-methyl-2-phenyl-4-(2-phenylhydrazono)-2,4-dihydro-3H-pyrazol-3-ones exist as hydrazone tautomers. The tautomeric state is not substantially influenced by nitro group substitution in the phenyl ring. Consequently, the studied compounds can be used as model tautomers in the NMR evaluation of the tautomeric state in various azo dyes in solution. According to the crystallographic data (obtained by us or available in the literature) the conclusions about the tautomerism of the studied compounds in solution are valid in solid state as well.
Faculty
Faculté des sciences et de médecine
Department
Département de Chimie
Language
  • English
Classification
Chemistry
License
License undefined
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https://folia.unifr.ch/unifr/documents/307936
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