[article]
| Titre : |
Revisiting tetranitrophenolsulfonephthalein |
| Type de document : |
texte imprimé |
| Auteurs : |
Nicolay O. Mchedlov-Petrossyan, Auteur ; Kateryna V. Roshchyna, Auteur ; Sergey V. Shekhovtsov, Auteur ; Sergey V. Eltsov, Auteur ; Oleksii S. Zozulia, Auteur ; Irina V. Omelchenko, Auteur ; Oleg V. Shishkin, Auteur |
| Année de publication : |
2015 |
| Article en page(s) : |
p. 236-244 |
| Note générale : |
Bibliogr. |
| Langues : |
Anglais (eng) |
| Catégories : |
Colorants -- Synthèse
Nitrophénols
|
| Index. décimale : |
667.2 Colorants et pigments |
| Résumé : |
Among the vast series of phenolsulfonephthalein dyes, the nitro derivatives and especially 3,3?,5,5?-tetranitrophenolsulfonephthalein (nitrophenol crimson) remain practically unexplored, whereas the halogen and alkyl derivatives have been studied comprehensively. This striking difference is probably due to the enormous influence of the four NO2 groups on the properties of the dye. As a result, the protolytic behaviour is unlike even that of tetrabromo phenolsulfonephthalein, and the recognised scheme of acid–base and tautomeric equilibrium of the sulfonephthaleins is unable to explain it. The molecular form H2R was isolated as a sultonic tautomer, and an X-ray crystal structure analysis was carried out. Our studies of the UV-vis absorption spectra in water, methanol, dimethyl sulfoxide, acetonitrile, acetone, and dichloromethane, as well as in aqueous micellar solutions of surfactants, allowed us to evaluate the true molar absorptivity of the dianion R2?, and to elucidate the enormous tendency to form yellow trianionic carbinol ROH3?, even in the presence of traces of H2O. Nuclear magnetic resonance and electrospray data confirm the proposed scheme of ionisation and tautomerism of nitrophenol crimson. |
| Note de contenu : |
- EXPERIMENTAL : Materials - Synthesis of the dye - Apparatus - Kinetic measurements
- RESULTS AND DISCUSSION : The structure of the dye in the solid state - Nitrophenol crimson in water - Nitrophenol crimson in organic solvents - Examining nitrophenol crimson solutions by the electrospray method - The monoanion problem |
| DOI : |
10.1111/cote.12145 |
| En ligne : |
https://onlinelibrary.wiley.com/doi/epdf/10.1111/cote.12145 |
| Format de la ressource électronique : |
Pdf |
| Permalink : |
https://e-campus.itech.fr/pmb/opac_css/index.php?lvl=notice_display&id=24126 |
in COLORATION TECHNOLOGY > Vol. 131, N° 3 (06/2015) . - p. 236-244
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Revisiting tetranitrophenolsulfonephthalein in COLORATION TECHNOLOGY, Vol. 131, N° 3 (06/2015)
