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PubMed1994

[Effect of quercetin on the course of chronic poisoning with fluorine compounds in rats].

Biochemical examinations in serum, homogenates and microsomal fraction of the liver, as well as biochemical and morphological examinations of liver tissue were performed in rats of Wistar strain exposed chronically for 6 months to ammonium fluoride vapours. A part of animals was protected with a mixture of sodium salts of quercetin synthetized in Inorganic Chemistry Department of the Technical University at Rzeszów, and added to the standard feed in a dose of 5 and 20 mg/kg body weight. It has been disclosed that NH4F causes disturbances in the activities of enzymes (cholinesterases, transaminases, alkaline and acid phosphatase), a rise of bilirubin concentration in serum, as well as disturbances in lipid metabolism, an increase in the content of total lipids, and disorders of lipid metabolism--increase in the content of total lipids, cholesterol and triglycerides, with phospholipids being decreased. The biochemical changes are accompanied by the hepatic tissue lesion. The use of quercetin alleviates, to a considerable degree, the biochemical and morphological disturbances due to protracted exposure to ammonium fluoride vapours.

Administration, Oral↗
PubMed2006

Electrolytic partial fluorination of organic compounds. 83. Anodic fluorination of N-substituted pyrroles and its synthetic applications to gem-difluorinated heterocyclic compounds.

Anodic fluorination of N-substituted pyrroles was carried out in MeCN containing supporting fluoride salts such as Et3N-nHF (n = 2-5) and Et4NF-4HF with use of platinum electrodes under constant current conditions. Anodic fluorination of N-methyl- and N-p-tosylpyrroles having an electron-withdrawing cyano group proceeded smoothly to provide the corresponding fluorinated products in moderate to excellent yields, while anodic fluorination of N-methylpyrrole devoid of an electron-withdrawing cyano group did not take place and a polymeric product was formed at the anode surface. In sharp contrast to the cases of N-methylpyrroles, even N-p-tosylpyrrole devoid of an electron-withdrawing cyano group underwent anodic fluorination efficiently. Diels-Alder reaction of 5,5-difluoro-1-methyl-3-pyrrolin-2-one (2e) derived from anodic fluorination of 2-cyano-1-methylpyrrole (2a) with various dienes was carried out to provide the cycloaddition products in excellent yields. Furthermore, Michael reaction of 2e with various nucleophiles was also successfully carried out to provide the Michael addition products in good to excellent yields.

Acetonitriles↗
PubMed1996

Identification and quantitation of gaseous compounds of fluorine generated in [18F]F2 target systems.

The first direct evidence for the chemical identity of the electrophilic fluorinating agents generated in 20Ne(d, alpha)18F (single-step), 18O(p,n)18F (single-step and two-step) and 16O(3He2+, p)18F (single-step) gas target systems, utilizing aluminum, silver, copper, nickel and gold plated copper target bodies, has been established with multinuclear NMR and mass spectral techniques. The major components of the reactive fraction from these targets were also quantitated using 19F NMR. Fluorine-19 NMR data of the reactive fraction of all proton and 3He2+ irradiated oxygen gas target systems showed the presence of oxygen difluoride in various proportions. Samples from the single-step method contained up to 20% OF2 while those from the two-step process had 0-5%. Fluorine nitrate (FONO2) was observed only as a minor component (0-3%) in the reactive fraction. The presence of OF2 and FONO2 was further confirmed by 17O and 15N NMR, respectively, using [17O]O2 and [15N]N2 spiked oxygen gas targets. The NMR results were supported by mass spectral data collected with a residual gas analyzer (RGA). Both 19F NMR and mass spectroscopy showed CF4 as the only major inert component in the single-step oxygen target products. As expected, the 19F NMR and mass spectral data showed that the reactive fraction of the neon gas target constituted only F2 and the inert fraction comprised of CF4 and NF3.

Fluorine Compounds↗
PubMed1997

Trends in Inversion Barriers of Group 15 Compounds. 3. Are Fluorinated Pyridone Derivatives Planar or Nonplanar?

Fluorinated compounds of 4-pyridone are studied using the semiempirical PM3 method, and the ab initio HF and MP2 methods. The perfluorinated derivative of 4-pyridone is predicted to have a nonplanar ring structure with the fluorine ligand at the nitrogen atom lying above the pyridine ring. The inversion barrier for the pentafluoro-4-pyridone is predicted to be 26 kJ/mol similar to that found for NH(3). This distortion corresponds to a static second-order Jahn-Teller effect and is expected to be experimentally detectable at low temperatures. N-Fluoro-4-pyridone is predicted to be nonplanar and has a small inversion barrier of 0.2 kJ/mol at the MP2 level. However, the maximum point of this barrier lies below the lowest zero-point out-of-plane inversion vibrational mode ((1)/(2) 84 cm(-1) identical with 0.5 kJ/mol). This corresponds to a dynamic Jahn-Teller effect and thus is experimentally difficult to verify. The MP2 calculations indicate that at least one fluorine atom is required at the ring nitrogen in order to achieve nonplanarity. Schleyer's negative-independent chemical shift method (NICS) is applied, and the results are used to discuss aromaticity in fluorinated pyridones. The NICS values show that succesive fluorination increases aromaticity. The vibrational spectra of all fluorinated pyridone derivatives are predicted. The vibrational spectrum of 4-pyridone is discussed in detail using a normal-mode analysis defined within a set of nonredundant internal coordinates.

Journal Article↗
PubMed2006

Special applications of fluorinated organic compounds.

The applications of fluorinated organic compounds (FOCs) as finishing agent for fabrics, components of extinguishing agents, electroplating bathes, lubricating oils, oxygen carriers in blood substitutes have been discussed. Recent achievements in methods of the fluorination and general principles of the synthesis of useful perfluorinated organic compounds are given as well.

Animals↗
PubMed2002

Structure of a fluorinated azoxy compound: fluoro(trifluoromethyl)-diazene-2-oxide, CF3N(O)NF.

A gas-phase electron diffraction study of the azoxy compound which was synthesized by the reaction of CF3NO with N2F4 in a Pyrex glass vessel results in a trans CF3N(O)NF structure (F trans to CF3), although quantum chemical calculations (MP2 and B3LYP) predict a greater stability of the cis CF3NN(O)F isomer by about 12 kcal/mol. The CF3 group eclipses the N=N double bond. The following skeletal geometric parameters (r(a) values with 3sigma uncertainties) were obtained: N=N 1.287(15) A; N=O 1.231(6) A; N-F 1.380(6) A; N-C 1.498(6) A; N=N=O 131.2(13) degrees; N=N-F 103.5(13) degrees; N=N-C 114.0(12) degrees. The bond lengths in CF3N(O)NF are compared to those in azo, nitryl, and nitrosyl compounds with fluorine and/or CF3 substituents.

Journal Article↗
PubMed2005

Electrolytic partial fluorination of organic compounds. 79. Anodic fluorination of spiropyrazoline-5,3'-chroman-4-ones and thiochromanone analogues. A route to aroyl fluoride derivatives.

[reaction: see text] Anodic fluorination of spiropyrazole-5,3'-chroman-4-ones and their thiochromanone analogues in dimethoxyethane containing Et4NF x 4HF resulted in ring opening of spiroheterocycles, which led to the formation of (5-pyrazolyl)methyl o-carbomethoxyphenyl ethers and their thioether analogues via benzoyl fluoride derivatives.

Chromans↗
PubMed2006

Synthesis and steric stabilization of silver nanoparticles in neat carbon dioxide solvent using fluorine-free compounds.

The adjustable solvent properties, vanishingly low surface tensions, and environmentally green characteristics of supercritical carbon dioxide present certain advantages in nanoparticles synthesis and processing. Unfortunately, most current techniques employed to synthesize and disperse nanoparticles in carbon dioxide use environmentally persistent fluorinated compounds as metal precursors and/or stabilizing ligands. This paper illustrates a one-step process for synthesis and stabilization of silver nanoparticles in carbon dioxide using only fluorine-free compounds. Isostearic acid coated silver nanoaparticles were formed and stably dispersed through arrested precipitation. Silver bis(3,5,5-trimethyl-1-hexyl)sulfosuccinate (Ag-AOT-TMH) was reduced in the presence of isostearic acid as a capping ligand in carbon dioxide solvent to form silver nanoparticles. The addition of cyclohexane as cosolvent or an increase in carbon dioxide solvent density enhances the dispersibility of the particles due to an increase in solvent strength. The dispersibility of the isostearic acid capped silver nanoparticles diminished with time until a stable dispersion was achieved due to the precipitation of a fraction of particle sizes too large to be stabilized by the solvent medium, thereby leaving a smaller size fraction of nanoparticles stably dispersed in the CO2 mixtures. This paper presents the one-step synthesis and stabilization of metallic nanoparticles in neat carbon dioxide without the aid of any fluorinated compounds.

Journal Article↗