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15N, 13C and 1H NMR study of tautomerism in 2-(phenyldiazenyl-4-substituted naphthalen-1-ols. Influence of substitution in passive components on azo-hydrazo tautomerism
Dyes and Pigments ( IF 4.1 ) Pub Date : 2021-01-13 , DOI: 10.1016/j.dyepig.2021.109149
Zdeňka Neuerová , Antonín Lyčka

The one- and two-dimensional 15N, 13C and 1H 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 15 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).



中文翻译:

15 N,13 C和1 H NMR研究2-(苯基二氮烯基-4-取代的萘-1-醇)中的互变异构现象。被动组分中的取代对偶氮-肼互变异构现象的影响

氯化苯重氮与4-R-萘-1-醇(R = NO 2 (1),Br (2),Cl (3)的偶合产物的一维和二维15 N,13 C和1 H NMR光谱,H (4),OCH 3 (5))进行了测量和分析。发现反应产物主要以形式存在。相反,在重氮盐取代基中的先前公布的影响,其中,多个电子受体类型原因的氢化偶氮化形式增加内容的取代基的,化合物中的情况1 - 5是完全相反的。此外,4-在4-硝基-2-[( E)-(4-硝基-苯基)二氮烯基]萘酞烯-1-醇(6)与4-硝基-N-萘酚相比,在被动成分的4位和活性成分的4位(即重氮盐)上结合的取代都更高2-[(E)-(苯基)二氮烯基]萘他烯-1-醇(1)。

更新日期:2021-01-29
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