Tautomerism in azo dyes: Border cases of azo and hydrazo tautomers as possible NMR reference compounds
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F62690094%3A18470%2F19%3A50015531" target="_blank" >RIV/62690094:18470/19:50015531 - isvavai.cz</a>
Result on the web
<a href="https://www.sciencedirect.com/science/article/abs/pii/S0143720818313536" target="_blank" >https://www.sciencedirect.com/science/article/abs/pii/S0143720818313536</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.dyepig.2019.02.015" target="_blank" >10.1016/j.dyepig.2019.02.015</a>
Alternative languages
Result language
angličtina
Original language name
Tautomerism in azo dyes: Border cases of azo and hydrazo tautomers as possible NMR reference compounds
Original language description
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-methy1-2-pheny1-4-(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-pheny1-4-(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.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
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Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2019
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Dyes and pigments
ISSN
0143-7208
e-ISSN
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Volume of the periodical
165
Issue of the periodical within the volume
JUN 2019
Country of publishing house
GB - UNITED KINGDOM
Number of pages
7
Pages from-to
157-163
UT code for WoS article
000463979700022
EID of the result in the Scopus database
2-s2.0-85061758241