Ueber Phenylhydrazinderivate des α‐ und β‐Naphtochinons. Identität des α‐Derivats mit dem Azoderivat des α‐Naphtols

Zincke, Th.; Bindewald, H.

doi:10.1002/cber.188401702282

Cited by 80 publications

(22 citation statements)

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“…42 As a result of the moderate energy gap between the enol (E) and the keto (K) tautomeric forms, the tautomeric equilibrium (Scheme 2) can be easily shifted in one or another direction by changing the solvent or/and the temperature. However, this equilibrium has never been shifted fully to one of the tautomers.…”

Section: Resultsmentioning

confidence: 99%

Tautocrowns: a concept for a sensing molecule with an active side-arm

et al. 2010

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A new sensing molecule containing aza-15-crown-5 as a receptor and 4-(phenyldiazenyl)naphthalen-1-ol as a signal converter has been synthesized. In the free ligand, the hydrogen bonding between the tautomeric OH group and the nitrogen atom from the macrocycle fully shifts the tautomeric equilibrium towards the enol form. The complexation reverses the equilibrium as a result of the strong interaction between the metal ion captured in the macrocyclic moiety and the tautomeric carbonyl group. The complex formation is accompanied by strong bathochromic (between 60 and 100 nm) and hyperchromic effects on the absorption spectra. Obviously, the tautomeric OH/C]O groups play the role of an active side-arm in the complexation, supporting it via formation of a 3D cavity and giving possibility for ejection of the guest compound under stimuli to shift the tautomeric process back.

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Section: Resultsmentioning

confidence: 99%

Tautocrowns: a concept for a sensing molecule with an active side-arm

et al. 2010

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“…This is not surprising when taking into account the larger dipole moment of the keto form and the observed keto dimerization in azodyes and Schiff bases even at low concentrations [36,37]. (2) is one of the first tautomeric compounds discovered [39] and, in spite of its limited practical applicability, is one of the most studied [40]. Its attractiveness is due to the lack of intramolecular hydrogen bonding, as for instance, in 4, which makes the tautomeric equilibrium very sensitive to changes in the solvent environment.…”

Section: Change In the Environment Affects The Equilibrium: Physical mentioning

confidence: 95%

Absorption UV–Vis Spectroscopy and Chemometrics: From Qualitative Conclusions to Quantitative Analysis

Antonov

2013

Tautomerism

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“…The model O ‐methyl product was prepared by methylation of hydroxyphenyl diazene 1 using dimethyl sulphate,13 trimethylsulphonium hydroxide,14 or diazomethane,15 while the N ‐methyl compound was obtained directly from naphthoquinone and α ‐methylphenylhydrazine sulphate 16. To the best of our knowledge, there have been no reports on the preparation of the N ‐methyl derivative via N ‐alkylation of the cheap and easily accessible hydroxyphenyl diazene 1 , as we propose in the current paper.…”

Section: Methodsmentioning

confidence: 99%

Gas‐phase tautomerism in 1‐phenylazonaphthalene‐4‐ol: verification of the responses of individual tautomers

Nedeltcheva

Kurteva

Damyanova

et al. 2009

Rapid Comm Mass Spectrometry

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Gas-phase tautomerism in 1-phenylazonaphthalene-4-ol (1) was studied by using electron ionization (EI) mass spectrometry on the basis of the fragmentations of the model enol and keto tautomers, where the movable proton is replaced by a methyl group. These fixed tautomers were obtained as an easy separable mixture by simple methylation of the cheap and easily accessible diazene (1). It was found that their EI mass spectral fragmentations are in full congruence with the already published theoretical predictions. The relative energies required for bond cleavage in 1 and its fixed tautomers were estimated by stepwise increasing of the electron energy of the ion source of the mass spectrometer. A simple equation for the approximate estimation of the molar fractions of the individual tautomers was suggested. It was shown that the enol form is dominant in the temperature range of 200-300 degrees C.

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Ueber Phenylhydrazinderivate des α‐ und β‐Naphtochinons. Identität des α‐Derivats mit dem Azoderivat des α‐Naphtols

Cited by 80 publications

References 0 publications

Tautocrowns: a concept for a sensing molecule with an active side-arm

Tautocrowns: a concept for a sensing molecule with an active side-arm

Absorption UV–Vis Spectroscopy and Chemometrics: From Qualitative Conclusions to Quantitative Analysis

Gas‐phase tautomerism in 1‐phenylazonaphthalene‐4‐ol: verification of the responses of individual tautomers

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