Isolation, structure, and properties of quinone-aci tautomer of a phenol-nitro compound related to eugenoxyacetic acid

Định, Nguyễn Năng; Huan, Trinh Thi; Toan, Duong Ngoc; Kimpende, Peter Mangwala; Meervelt, Luc Van

doi:10.1016/j.molstruc.2010.07.005

Cited by 4 publications

(6 citation statements)

References 19 publications

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“…It is possible that 2 was converted into the more stable form (a nitrophenol conjurated with the side chain) and the phenolic proton was lost as shown in Scheme 3. In addition, the similarity in 1 H NMR spectra of 2, 3 and 1 (previously reported [18]) indicates that they have the same aci-quinone structure. The absence of the signals of the ethyl group, the presence of the broadened signal of the NH 2 group in 1 H NMR spectrum of 4 ( Table 1) and the strong decrease in the frequency of carbonyl group of 4 (1699 cm -1 ) in comparison with that of 3 (1752 cm -1 ) are clear evidences for the formation of hydrazide 4.…”

Section: Resultssupporting

confidence: 65%

“…Aci-quinone 2 was prepared by treatment of methyleugenol with excess nitric acid in the acetic acid according to the procedure described for the preparation of aci-quinone 1 [18]. The formation of aci-quinone 2 can be briefly explained as shown in Scheme 1.…”

Section: Resultsmentioning

confidence: 99%

“…Subsequently, the phenolic hydroxyl group was acylated, followed by the replacement of the nitrate group to give 6a and 6, respectively (Scheme 4). Compound 6a was identified as 2-acetoxy-4-(2-acetoxy-3nitropropyl)-5-nitrophenoxyacetic acid, which had been isolated and characterized [18]. The structure of compound 6 was examined by IR and NMR spectroscopic methods (see Experimental section and Table 1).…”

Section: Reaction Of Aci-quinones 1 and 2 With Acetic Anhydridementioning

confidence: 99%

“…. This compound was obtained by treating eugenoxyacetic acid with excess amounts of nitric acid in acetic acid [18].…”

Section: Preparation 4-(aci-nitro)-2-(carboxymethoxy)-5-(3-nitro-2-(nmentioning

confidence: 99%

“…In our previous work [18] the isolation, structure and double tautomerization of an aci-quinone compound, 4-(aci-nitro)-2-(carboxymethoxy)-5-(3-nitro-2-(nitrooxy)propyl)-cyclohexa-2,5-dienone (1) related to eugenoxyacetic acid have been reported. The aci-quinone 1 was used as the key compound for the synthesis of novel polysubstituted quinolines [19].…”

Section: Introductionmentioning

confidence: 99%

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Aci-Quinone Compounds from Eugenoxyacetic Acid and Methyleugenol: Preparation and Reaction

Định

Hien²,

Ngọc³

et al. 2015

COS

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A new aci-quinone compound, 4-(aci-nitro)-2-(methoxy)-5-(3-nitro-2-(nitrooxy)propyl)-cyclohexa-2,5dienone (2), an analog to 4-(aci-nitro)-2-(carboxymethoxy)-5-(3-nitro-2-(nitrooxy)propyl)-cyclohexa-2,5-dienone (1), was successfully synthesized and fully characterized by spectroscopic methods. The reactions of 1 and 2 with various reagents such as hydroxylamine, acetic anhydride, semicarbazide and thiosemicarbazide were examined. The structure of 11 obtained new compounds was established by IR, 1 H NMR, 13 C NMR, HMBC and MS spectra. It was shown that the unstable, sensitive aci-quinone structure of compounds 1 and 2 can exist in anhydrous organic solvents such as AcOEt, EtOH but in the presence of water, H + , HOor at high temperatures, the aci-quinone structure of both 1 and 2 tendentiously transformed into the more stable nitro-phenol form.

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Section: Resultssupporting

confidence: 65%

Section: Resultsmentioning

confidence: 99%

Section: Reaction Of Aci-quinones 1 and 2 With Acetic Anhydridementioning

confidence: 99%

“…. This compound was obtained by treating eugenoxyacetic acid with excess amounts of nitric acid in acetic acid [18].…”

Section: Preparation 4-(aci-nitro)-2-(carboxymethoxy)-5-(3-nitro-2-(nmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Aci-Quinone Compounds from Eugenoxyacetic Acid and Methyleugenol: Preparation and Reaction

Định

Hien²,

Ngọc³

et al. 2015

COS

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Chemical characterisation of a new estuarine pollutant (2,4-Dichloro-6-Nitrophenol) and assessment of the acute toxicity of its quinoid form forArtemia salina

Tognazzi

Dattilo

Bracchini

et al. 2012

International Journal of Environmental Analytical Chemistry

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It is known that the compound 2,4-dichloro-6-nitrophenol (2,4DC6NP) is formed upon nitration of 2,4-dichlorophenol, which in turn is a transformation intermediate of the herbicide dichlorprop. However, the chemical and spectroscopic characteristics of 2,4DC6NP, as well as its toxicity, are poorly known. This work shows that 2,4DC6NP behaves as a diprotic acid in aqueous solutions, with pK a values of 3.0 AE 0.9 and 4.9 AE 0.5. At pH < 3, 2,4DC6NP would undergo protonation. The absorption spectra suggest that anionic 2,4DC6NP, which prevails at pH > 5 would have an ortho-quinoid structure that is responsible for the absorption peak centred at 428 nm. Considering that 2,4DC6NP has been detected in the brackish lagoons of the Rhoˆne delta (southern France), where its levels are comparable to those of the parent herbicide, it is necessary to examine the possible effects of 2,4DC6NP on the species living in that environment. For this reason, the acute toxicity of the anionic form of 2,4DC6NP was assessed for the brine shrimp Artemia salina, a zooplankton species that lives both in brackish and in saline aquatic environments. The toxicity test yielded a LC 20 value of 8 AE 2 mg L À1 and a LC 50 value of 18.7 AE 0.8 mg L À1 . Such values are safely higher than the maximum detected concentration of 2,4DC6NP in the Rhoˆne delta lagoons. Further studies should be concentrated on the long-term effects of 2,4DC6NP, and in particular on its potential genotoxicity.

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Bioactivity and molecular properties of Phenoxyacetic Acids Derived from Eugenol and Guaiacol compared to the herbicide 2,4-D

Alves

Pinheiro

Fontes

et al. 2021

An. Acad. Bras. Ciênc.

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Herbicides are agrochemicals applied in the control of weeds. With the frequent and repetitive use of these substances, serious problems have been reported.Compounds of natural origin and their derivatives are attractive options to obtain new compounds with herbicidal properties. By aiming to develop compounds with potentiated herbicidal activity, phenoxyacetic acids were synthesized from eugenol and guaiacol. The synthesized compounds were characterized and the herbicidal potential of phenoxyacetic acids and precursors was evaluated through bioassays regarding the germination and initial development of Lactuca sativa and Sorghum bicolor seedlings, with the induction of DNA damage. The induction of changes in the mitotic cycle of meristematic cells of roots of L. sativa was also analyzed. At the concentration of 3 mmol L -1 , phenols and their respective phenoxyacetic acids presented phytotoxic and cytotoxic activities in L. sativa and S. bicolor. Eugenol and guaiacol also presented genotoxic action in L. sativa. The toxic effect of eugenoxyacetic acid was more pronounced in L. sativa than in S. bicolor, similar to the commercial 2,4-D herbicide. Molecular properties of the phenols and their derivatives phenoxyacetic acids were compared with the ones obtained for the herbicide 2,4-D, where it was found a correlation between their molecular properties and bioactivity.

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Isolation, structure, and properties of quinone-aci tautomer of a phenol-nitro compound related to eugenoxyacetic acid

Cited by 4 publications

References 19 publications

Aci-Quinone Compounds from Eugenoxyacetic Acid and Methyleugenol: Preparation and Reaction

Aci-Quinone Compounds from Eugenoxyacetic Acid and Methyleugenol: Preparation and Reaction

Chemical characterisation of a new estuarine pollutant (2,4-Dichloro-6-Nitrophenol) and assessment of the acute toxicity of its quinoid form forArtemia salina

Bioactivity and molecular properties of Phenoxyacetic Acids Derived from Eugenol and Guaiacol compared to the herbicide 2,4-D

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