Journal
DYES AND PIGMENTS
Volume 188, Issue -, Pages -Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.dyepig.2021.109149
Keywords
Azo compounds; N-15; C-13 and H-1 NMR; Azo-hydrazo tautomerism
Funding
- Faculty of Science, University of Hradec Kralove
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The one- and two-dimensional NMR spectra of benzenediazonium chloride coupling product with 4-R-naphthalene-1-ols were measured and analysed, revealing that the reaction products exist predominantly in hydrazone forms. Contrary to previous studies, it was found that more electron acceptor types of substituents actually cause an increase in hydrazone content in the compounds.
The one-and two-dimensional N-15, C-13 and H-1 NMR spectra of benzenediazonium chloride coupling product with 4-R-naphthalene-1-ols (R = NO2 (1), Br (2), Cl (3), H (4), OCH3 (5)) were measured and analysed. It was found that the reaction products exist predominantly in hydrazone forms. Contrary to previously published influence of substituents in diazonium salts, where more electron acceptor types of substituents cause increase contents of hydrazo forms, the situation in compounds 1-5 is completely opposite. Moreover, hydrazone content in 4-nitro-2-[(E)-(4-nitro-phenyl)diazenyl]naphtalen-1-ol (6) combining substitution both in position 4 of passive component and position 4 of active component (i. e. diazonium salt) is higher compared with that in 4-nitro-2-[(E)-(phenyl)diazenyl]naphtalen-1-ol (1).
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