Dediazoniation of p-hydroxybenzenediazonium ion in a neutral aqueous medium

Quintero, B.; Morales, José Jorge; Quirós, Miguel; Martinez-Puentedura, M.I; Cabeza, Marı́a del Carmen

doi:10.1016/s0891-5849(00)00321-x

Cited by 16 publications

(15 citation statements)

References 46 publications

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“…The coincidence of the absorption maxima registered with the solution of PDQ in DMSO with those shown by non-protonated species deriving from PDQ in aqueous medium [13,14] indicates that the observed experimental behaviour corresponds to the equilibrium in Fig. 2, in which DMSO acts as an excellent proton-acceptor, giving the deprotonated species deriving from PDQ, formulated as a resonance hybrid with two canonical forms, which can be homolytically dediazonated in a neutral aqueous medium, as proved elsewhere [13].…”

Section: Pdq Dediazoniationsupporting

confidence: 67%

“…In previous studies into PDQ dediazoniation [13][14][15] our results have shown that in a neutral aqueous medium in the dark PDQ dediazoniation is a homolytic process. This homolytic degradation is triggered by the hydroxyl anion but the primary products then produce a selfcatalyzed reaction in which aryl, hydroxyphenylperoxyl and semiquinone radicals appear to be involved.…”

Section: Introductionmentioning

confidence: 51%

“…PDQ was synthesized in our laboratory according to the procedure indicated elsewhere [13] and stored at −18 • C in darkness to avoid degradation by exposure to light. Dimethylsulfoxide (DMSO) was from Merck (Madrid, Spain) and was used as received without further purification.…”

Section: Chemicalsmentioning

confidence: 99%

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Tumor-promoting activity of p-hydroxybenzenediazonium is accelerated in Mg-deficient rats

Quintero

Planells

Cabeza

et al. 2006

Chemico-Biological Interactions

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Tumor-promoting activity caused by the short-term administration of p-hydroxybenzenediazonium (PDQ) has been assayed in rats fed on a Mg-deficient diet as a reference model versus rats fed on a standard diet as controls. For 5 weeks groups of 20 rats, fed either on the Mg-deficient or standard diet, were treated simultaneously with PDQ. A group of 10 Mg-deficient rats remained untreated. Topical application of PDQ was followed by the appearance of macroscopic alterations in the skin, which were more evident in the Mg-deficient rats. No deaths occurred during the treatment. After 5 weeks' PDQ treatment the rats were killed and histological analyses were made. Tissues from the skin, liver, heart, kidney, lung and thymus were screened by conventional staining methods. Both the PDQ-treated Mg-deficient and PDQ-treated control rats presented tissue lesions, although to a different extent. The untreated Mg-deficient rats showed no such lesions. Mg-deficient rats treated with PDQ developed significant incipient fibrosarcomas (p < 0.05) and extended hyperplasia (p < 0.001), particularly in the skin, accompanied by a significant increase in the thickness of collagen (mean value: 445.4 ± 47.2 m, p < 0.05) compared to the control PDQ-treated group (mean values: 258.7 ± 36.4 m). The overall results provide objective proof of tumor-promoting activity after 5 weeks' treatment with PDQ. Such a fast response is interpreted as being linked to the increased vulnerability of the membrane caused by Mg deficiency, which would more readily facilitate the toxic activity of p-hydroxybenzenediazonium ions.

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Section: Pdq Dediazoniationsupporting

confidence: 67%

Section: Introductionmentioning

confidence: 51%

See 1 more Smart Citation

Tumor-promoting activity of p-hydroxybenzenediazonium is accelerated in Mg-deficient rats

Quintero

Planells

Cabeza

et al. 2006

Chemico-Biological Interactions

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“…Given the large number of reports published in this field in the past 150 years, it is surprising that there is one group of diazonium ions for which radical reactions remained practically unknown. Driven by the interest to find out whether this exclusion is due to the unique reactivity of the hydroxy-substituted aryl radicals 1 [4] and 2, [5,6] or is rather a consequence of special properties of the related arenediazonium ions 3 and 4 (e.g., the possible formation of quinonediazides), we revisited the chemistry of these compounds and their reactive intermediates. Herein, we summarized our first results.…”

mentioning

confidence: 99%

Hydroxy‐ and Aminophenyl Radicals from Arenediazonium Salts

Pratsch

Anger

Ritter

et al. 2011

Chemistry A European J

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A buried polar bilayer interface composed of interdigitated peptide ends and a high density of CF3COO− counterions passifying lysine amines are identified in nanotubes obtained by self‐assembly of short peptides. The structure reveals distinct characteristics that differentiate peptide bilayers and lipid bilayers that can now be exploited for the construction of lipid‐like nanomaterials with protein functionality.

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“…[41] In addition, the phenol formed upon dediazotation might also lead to crosslinking. If the diazotation is performed at room temperature or 0 8C, different resins are obtained with distinct thermochemical features (see below).…”

mentioning

confidence: 99%