104-91-6Relevant articles and documents
Enthalpies of combustion of 2-iodosobenzoic acid and 4-nitrosophenol: The dissociation enthalpy of the I-O bond
Ribeiro Da Silva, Maria D. M. C.,Matos, M. Agostinha R.,Ferrao, Maria Luisa C. C. H.,Amaral, Luisa M. P. F.,Miranda, Margarida S.,Acree Jr.,Pilcher
, p. 1551 - 1559 (1999)
The standard (po = 0.1 MPa) molar enthalpies of combustion in oxygen, at T = 298.15 K, for crystalline 2-iodosobenzoic acid, (OI)C6H4COOH, and 4-nitrosophenol, (ON)C6H4OH, were measured by rotating-bomb calorimetry and static-bomb calorimetry, respectively. These values were used to derive the standard molar enthalpies of formation of the crystalline compounds. ΔfHom(cr)/(kJ · mol-1) 2-iodosobenzoic acid 2-(OI)C6H4COOH -336.9 ± 2.5 4-nitrosophenol 4-(ON)C6H4OH -70.2 ± 2.1 An indirect method was used for assessing the dissociation enthalpy of the (I-O) bond in the iodoso derivative, Dom(I-O)/(kJ · mol-1) = (264.5 ± 8.1), which is the first value reported for an iodine-oxygen bond in an organic molecule.
Schmid et al.
, p. 781 (1966)
Investigation of photoelectrocatalytic activity of Cu2O nanoparticles for p-nitrophenol using rotating ring-disk electrode and application for electrocatalytic determination
Gu, Yong-E,Zhang, Yuzhen,Zhang, Fengyuan,Wei, Jinping,Wang, Chunming,Du, Yongling,Ye, Weichun
, p. 953 - 958 (2010)
A cuprous oxide (Cu2O) nanoparticles modified Pt rotating ring-disk electrode (RRDE) was successfully fabricated, and the electrocatalytic determination of p-nitrophenol (PNP) using this electrode was developed. Cu2O nanoparticles were obtained by reducing the copper-citrate complex with hydrazine hydrate (N2H4·H 2O) in a template-free process. The hydrodynamic differential pulse voltammetry (HDPV) technique was applied for in situ monitor the photoelectrochemical behavior of PNP under visible light using nano-Cu 2O modified Pt RRDE as working electrode. PNP undergoes photoelectrocatalytic degradation on nano-Cu2O modified disk to give electroactive p-hydroxylamino phenol species which is compulsive transported and can only be detected at ring electrode at around 0.05 V with oxidation signal. The effects of illumination time, applied bias potential, rotation rates and pH of the reaction medium have been discussed. Under optimized conditions for electrocatalytic determination, the anodic current is linear with PNP concentration in the range of 1.0 × 10-5 to 1.0 × 10 -3 M, with a detection limit of 1.0 × 10-7 M and good precision (RSD = 2.8%, n = 10). The detection limit could be improved to 1.0 × 10-8 M by given illumination time. The proposed nano-Cu2O modified RRDE can be potentially applied for electrochemical detection of p-nitrophenol. And it also indicated that modified RRDE technique is a promising way for photoelecrocatalytic degradation and mechanism analysis of organic pollutants.
Nitrosation kinetics of phenolic components of foods and beverages
Paz Ferna?ndez-Liencres,Calle, Emilio,Gonza?lez-Mancebo, Samuel,Casado?, Julio,Quintero, Bartolome?
, p. 119 - 125 (1997)
The kinetics of the reactions between sodium nitrite and phenol or m-, o-, or p-cresol in potassium hydrogen phthalate buffers of pH 2.5-5.7 were determined by integration of the monitored absorbance of the C-nitroso reaction products. At pH > 3, the dominant reaction was C-nitrosation through a mechanism that appears to consist of a diffusion-controlled attack on the nitrosatable substrate by NO+/NO2H2+ ions followed by a slow proton transfer step; the latter step is supported by the observation of basic catalysis by the buffer which does not form alternative nitrosating agents as nitrosyl compounds. The catalytic coefficients of both anionic forms of the buffer have been determined. The observed order of substrate reactivities (o-cresol ≈ m-cresol > phenol ? p-cresol) is explained by the hyperconjugative effect of the methyl group in o- and m-cresol, and by its blocking the para position in p-cresol. Analysis of a plot of ΔH# against ΔS# shows that the reaction with p-cresol differs from those with o- and m-cresol as regards the formation and decomposition of the transition state. The genotoxicity of nitrosatable phenols is compared with their reactivity with NO+/NO2H2+.
Nitrosation of phenolic compounds: Inhibition and enhancement
Gonzalez-Mancebo, Samuel,Garcia-Santos, M. Pilar,Hernandez-Benito, Jesus,Calle, Emilio,Casado, Julio
, p. 2235 - 2240 (1999)
The nitrosation of phenol, m-, o-, and p-cresol, 2,3-, 3,5-, and 2,6- dimethylphenol, 3,5-di-tert-butylphenol, 2,4,6-trimethylphenol, o- chlorophenol, and o-bromophenol was studied. Kinetic monitoring of the reactions was accomplished by spectrophotometric analysis of the products at 345 nm. At pH > 3, the dominant reaction was C-nitrosation through a mechanism that appears to consist of an attack on the nitrosatable substrate by NO+/NO2H2+, followed by a slow proton transfer. The finding of an isokinetic relationship supports the idea that the same mechanisms operates throughout the series. The observed sequence of nitrosatable substrate reactivities is explained by (i) the preferred para-orientation of the hydroxyl group for the electrophilic attack of nitrosating agents, (ii) steric hindrance of alkyl substituents, which reduces or prevents attack by nitrosating agents, and (iii) the hyperconjugative effect of the methyl substituent, which causes electronic charge to flow into the aromatic nucleus, as well as the opposite electronic withdrawing effect induced by halogen substituents. The results show that potential nitrosation of widespread environmental species such as chlorophenols is negligible, but more attention should be paid to polyphenols with strongly nucleophilic carbon atoms.
Tungstate-supported silica-coated magnetite nanoparticles: a novel magnetically recoverable nanocatalyst for green synthesis of nitroso arenes
Jadidi Nejad, Masoume,Yazdani, Elahe,Kazemi Miraki, Maryam,Heydari, Akbar
, p. 1575 - 1583 (2019/09/09)
Tungstate ion was heterogenized on the silica-coated magnetite nanoparticles and applied for the selective oxidation of anilines to nitroso arenes—with hydrogen peroxide/urea as oxidant in dimethyl carbonate as solvent—in moderate–good yields (40–96%). The catalyst was characterized using different techniques including Fourier-transform infrared spectroscopy, X-ray powder diffraction, vibrating sample magnetometry, scanning electron microscopy, energy dispersive X-ray and inductively coupled plasma atomic emission spectroscopy (ICP-AES). The catalyst was easily recovered using an external magnet and reused for six times.
Nitric Oxide Is Reduced to HNO by Proton-Coupled Nucleophilic Attack by Ascorbate, Tyrosine, and Other Alcohols. A New Route to HNO in Biological Media?
Suarez, Sebastián A.,Neuman, Nicolás I.,Mu?oz, Martina,álvarez, Lucía,Bikiel, Damián E.,Brondino, Carlos D.,Ivanovi?-Burmazovi?, Ivana,Miljkovic, Jan Lj.,Filipovic, Milos R.,Martí, Marcelo A.,Doctorovich, Fabio
supporting information, p. 4720 - 4727 (2015/04/27)
The role of NO in biology is well established. However, an increasing body of evidence suggests that azanone (HNO), could also be involved in biological processes, some of which are attributed to NO. In this context, one of the most important and yet unanswered questions is whether and how HNO is produced in vivo. A possible route concerns the chemical or enzymatic reduction of NO. In the present work, we have taken advantage of a selective HNO sensing method, to show that NO is reduced to HNO by biologically relevant alcohols with moderate reducing capacity, such as ascorbate or tyrosine. The proposed mechanism involves a nucleophilic attack to NO by the alcohol, coupled to a proton transfer (PCNA: proton-coupled nucleophilic attack) and a subsequent decomposition of the so-produced radical to yield HNO and an alkoxyl radical. (Graph Presented).
