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  • Chemical Engineering  (615)
  • Organic Chemistry  (391)
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  • 1990-1994  (574)
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  • 1
    Electronic Resource
    Electronic Resource
    Plasma protein binding of ketoprofen enantiomers in man: Method development and its application (1991)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 3 (1991), S. 460-466 
    Details
    ISSN: 0899-0042
    Keywords: ketoprofen ; stereoisomers ; plasma binding ; binding linearity and competition ; ketoprofen glucuronides ; 2-arylpropanoic acids ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The protein binding of ketoprofen enantiomers was investigated in human plasma at physiological pH and temperature by ultrafiltration. 14C-labelled (RS)-ketoprofen was synthesized and purified by high-performance liquid chromatography and utilized as a means of quantifying the unbound species. In vitro studies were conducted with plasma obtained from six healthy volunteers. The plasma was spiked with (R)-ketoprofen alone, (S)-ketoprofen alone, and (RS)-ketoprofen in the enantiomeric concentration range of 1.0 to 19.0 μg/ml. The plasma protein binding of ketoprofen was nonenantioselective. At a racemic drug concentration of 2.0 μg/ml the mean (± SD) percentage unbound of (R)-ketoprofen was 0.80 (± 0.15)%. The corresponding value for (S)-ketoprofen, 0.78 (± 0.18)%, was not statistically different (P 〉 0.05). At this racemic drug concentration (2.0 μg/ml) the percentage unbound of each enantiomer was unaffected (P 〉 0.05) by the presence of the glucuronoconjugates of ketoprofen (10 μg/ml) in plasma. At clinically relevant concentrations, the plasma binding of ketoprofen did not exhibit enantioselectivity or concentration dependence nor was the binding of either enantiomer influenced by its optical antipode (P 〉 0.05).
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530030609
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  • 2
    Electronic Resource
    Electronic Resource
    Interaction of pirprofen enantiomers with human serum albumin (1991)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 3 (1991), S. 412-417 
    Details
    ISSN: 0899-0042
    Keywords: pirprofen enantiomers ; human serum albumin ; binding ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The interaction of pirprofen enantiomers with human serum albumin (HSA) was investigated by means of high-performance liquid chromatography (HPLC), circular dichroism (CD), and 1H NMR spectroscopy. HPLC experiments indicated that both pirprofen enantiomers were bound to one class of high-affinity binding sites (n(+) = 1.91 ± 0.13, K(+) = (4.09 ± 0.64) × 105 M-1, n(-) = 2.07 ± 0.13, K(-) = (6.56 ± 1.35) × 105 M-1) together with nonspecific binding (n′K′(+) = (1.51 ± 0.21) × 104 M-1, n′K′(-) = (0.88 ± 0.13) × 104 M-1). Slight stereoselectivity in specific binding was demonstrated by the difference in product n(+)K(+) = (0.77 ± 0.08) × 106 M-1 vs. n(-)K(-) = (1.30 ± 0.21) × 106 M-1, i.e., the ratio n(-)K(-)/n(+)K(+) = 1.7. CD measurements showed changes in the binding sites located on the aromatic amino acid side chains (a small positive band at 315 nm and a pronounced negative extrinsic Cotton effect in the region 250-280 nm). The protein remains, however, in its predominantly alpha-helical conformation. The 1H NMR difference spectra confirmed that both pirprofen enantiomers interacted with HSA specifically, most probably with site II on the albumin molecule.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530030506
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  • 3
    Electronic Resource
    Electronic Resource
    Estimation of ionization constants of azo dyes and related aromatic amines: Environmental implication (1994)
    Chichester : Wiley-Blackwell
    Journal of Physical Organic Chemistry 7 (1994), S. 122-141 
    Details
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: Ionization constants for 214 dye molecules were calculated from molecular structures using the chemical reactivity models developed in SPARC (SPARC Performs Automated Reasoning in Chemistry). These models used fundamental chemical structure theory to predict chemical reactivities for a wide range of organic molecules from molecular structure. The energy differences between the protonated state and the unprotonated state for a molecule of interest are factored into mechanistic components including the electrostatic and resonance contributions and any additional contributions to these energy differences. The RMS deviation was found to be less than 0·62 pKa units, which is similar to the experimental error.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/poc.610070304
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  • 4
    Electronic Resource
    Electronic Resource
    Stereochemistry and kinetics of methoxide ion substitution in (Z)- and (E)-O-methylbenzohydroximoyl cyanides (1994)
    Chichester : Wiley-Blackwell
    Journal of Physical Organic Chemistry 7 (1994), S. 352-358 
    Details
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: The stereochemistry and kinetics of the methoxide ion substitution reactions (Z)- and (E)-methylbenzohydroximoyl cyanidc [PhC(CN)=NOCH3] were investigated. The reaction of the (Z)-hydroximoyl cyanide with sodium methoxide in DMSO-methanol (9:1) solution at 44·8°C gives a mixture of methyl (Z)-O-methylbenzohydroximate [PhC(OCH3)=NOCH3] and the O-methyloxime of α-ketophenylacetamide PhC(CONH2)=NOCH3. The (E)-hydroximoyl cyanide undergoes methoxide ion-catalyzed isomerization to the E-isomer faster than it undergoes nucleophilic substitution. These observations were interpreted in terms of an addition-elimination mechanism in which the rate-limiting step is elimination of the nucleofuge (AN + DN#).
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/poc.610070704
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  • 5
    Electronic Resource
    Electronic Resource
    3-Methylcarboxy-1H-indazole. Theoretical study of its formation via intramolecular aliphatic diazonium coupling and x-ray crystal structure (1993)
    Chichester : Wiley-Blackwell
    Journal of Physical Organic Chemistry 6 (1993), S. 201-214 
    Details
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: The methyl ester of 1H-indazole-3-carboxylic acid (2-Me) is formed in the diazotization of o-aminophenylacetic acid to o-diazoniumphenylacetic acid (1) in an intramolecular aliphatic diazonium coupling. 2-Me was identified and characterized by single-crystal x-ray diffraction and found to crystallize as hydrogen-bonded trimers of crystallographically independent molecules. The methylcarboxy groups are rotated slightly out of the best plane of the trimer resulting in only a pseudo-threefold axis. The crystal structure of 2-Me is compared with other indazoles and pyrazole. Regioselective electrophilic diazonium ion addition to the enol tautomer of 1 and subsequent hyrazone-azo tautomerization are proposed as a possible mechanism for indazole formation under acidic conditions. The tautomerization equilibrium between acetic acid and its enol 1,2-dihydroxyethene was studied and the effects of phenyl and o-diazoniumphenyl substitution on this equilibrium were explored with semi-empirical quantum mechanical methods. The performance of the semi-empirical method was assessed by comparison with ab initio and/or experimental data. It was found that the enol of o-diazoniumphenylacetic acid is stabilized greatly owing to extended conjugation and push-pull interactions in the enol form. These results suggest that the enol tautomer might be a viable reactive intermediate that warrants considerations in discussions of reaction mechanisms.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/poc.610060403
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  • 6
    Electronic Resource
    Electronic Resource
    Structure-property modifications by fabrication operations (1964)
    Stamford, Conn. [u.a.] : Wiley-Blackwell
    Polymer Engineering and Science 4 (1964), S. 165-168 
    Details
    ISSN: 0032-3888
    Keywords: Chemistry ; Chemical Engineering
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Mechanical Engineering, Materials Science, Production Engineering, Mining and Metallurgy, Traffic Engineering, Precision Mechanics , Physics
    Notes: Studies of polymer morphology under ideal conditions approaching equilibrium structures have been shown to be valuable in the development of an understanding of the relationship of properties to structure. Practical fabrication operations do not permit the achievement of equilibrium structures in commercial products and its is therefore necessary to study the effects of processing on the actual structures that result. In addition, an understanding of the effects of processing variables on properties permits the development of fabrication operations which can be directed toward the improvement of properties. Topics covered include the effects of hydrostatic pressure during processing, effects of combinations of pressure and thermal history, relationships between thermal history and crystallization rates in isotactic polymers and the kinetic and morphological effects of flow deformation on crystallizable plastics.
    Additional Material: 9 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pen.760040306
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  • 7
    Electronic Resource
    Electronic Resource
    Formation constants in C—H hydrogen bonding. 2. Alkynes and polyhalobenzenes with hexamethylphosphoric triamide in cyclohexane solution (1990)
    Chichester : Wiley-Blackwell
    Journal of Physical Organic Chemistry 3 (1990), S. 659-669 
    Details
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: Formation constants, K, for hydrogen bonding of weak C—H donors with hexamethylphosphoric triamide were measured in cyclohexane at 35°C by PMR spectroscopy; data were analyzed by the Higuchi method. Donors include terminal alkynes and series of polyfluoro-, polychloro- and polybromobenzenes. The K values for many of these are too small to measure in CCl4. For RC≡CH, K decreases in the order R = BrCH2 〉 C6H5 〉 C2H5O 〉 tert-butyl. For polyhalobenzenes, K is generally larger for F than Cl or Br, and meta halogens facilitate hydrogen bonding most effectively. Among tetrahalobenzenes, 1,2,3,4-isomers show the least evidence of 2:1 complex formation. Pentachlorobenzene has a smaller K than its 1,2,3,4-tetrachlor analog even after statistical correction; for C6HX5, K decreases in the order F 〉 Cl 〉 Br; the K values for 1,3,5-trihalobenzenes are closely similar; and 1,3,5-tribromo-2,4-dimethylbenzene shows no evidence of hydrogen bonding by PMR. The last three observations suggest that buttressing is important in the C6HX5 structure, at least with Cl and Br. A value of K for benzene was measured, suggesting for the first time that the H atoms of benzene engage in hydrogen bonding. The result compares well with values extrapolated from data for polyfluoro- but not polychlorobenzenes, again probably because of buttressing in the latter.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/poc.610031007
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  • 8
    Electronic Resource
    Electronic Resource
    Homoaromaticity of decamethyl[5]pericyclyne (1993)
    Chichester : Wiley-Blackwell
    Journal of Physical Organic Chemistry 6 (1993), S. 316-318 
    Details
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: It is shown that a theoretical computation of the Dewar resonance energy of decamethyl [5] pericyclyne should give the same value for the homoaromaticity of this compound as that calculated earlier from heat of hydrogenation measurements. Both methods show this quantity to be small, but the accuracy of the methods appears insufficient for more exact agreement.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/poc.610060510
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  • 9
    Electronic Resource
    Electronic Resource
    Dielectric characterization of water sorption in epoxy resin matrices (1993)
    Stamford, Conn. [u.a.] : Wiley-Blackwell
    Polymer Engineering and Science 33 (1993), S. 75-82 
    Details
    ISSN: 0032-3888
    Keywords: Chemistry ; Chemical Engineering
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Mechanical Engineering, Materials Science, Production Engineering, Mining and Metallurgy, Traffic Engineering, Precision Mechanics , Physics
    Notes: Water sorption in epoxy based materials was analyzed by dielectric spectroscopy using remote sensors. A method to determine diffusion coefficients from the changes in permittivity during water absorption is proposed and was verified experimentally by comparison with standard water gain measurements. Although the technique is limited by electrode polarization phenomena, it is sensitive to the presence of water molecules and is capable of detecting different levels of water concentration as a function of frequency. The utilization of remote sensors demonstrated the capability of dielectric analysis to be applied both in the laboratory environment, and on a larger scale, as a nondestructive technique for monitoring environmental changes in actual polymer matrix composite parts.
    Additional Material: 11 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pen.760330204
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  • 10
    Electronic Resource
    Electronic Resource
    Differential scanning calorimetry analysis of thermoset cure kinetics: Phenolic resole resin (1991)
    Stamford, Conn. [u.a.] : Wiley-Blackwell
    Polymer Engineering and Science 31 (1991), S. 1665-1669 
    Details
    ISSN: 0032-3888
    Keywords: Chemistry ; Chemical Engineering
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Mechanical Engineering, Materials Science, Production Engineering, Mining and Metallurgy, Traffic Engineering, Precision Mechanics , Physics
    Notes: The Differential Scanning Calorimetry (DSC) trace for a commercial phenolic resole resin shows two distinct peaks. Assuming that these represent two independent cure reactions results in a kinetic model of the form: \documentclass{article}\pagestyle{empty}\begin{document}$$ \frac{{dx}}{{dt}} = p\kappa _1 \left({1 - x_1} \right)^{n_1} + \left({1 - p} \right)\kappa _2 \left({1 - x_2} \right)^{n_2} $$\end{document} with κi = κio exp(-Bi/T).The Arrhenius parameters were estimated from a plot of ln(β/Tp2) versus 1/Tp. The parameters, p, n1, and n2 were obtained by writing the DSC response predicted by the equation above in terms of a function which contains temperature as the only variable. \documentclass{article}\pagestyle{empty}\begin{document}$$ \dot q = q_{tot} \left[{p\kappa _1 \left({1 - \theta _1 /r_1} \right)^{r_1 - 1} + \left({1 - p} \right)\kappa _2 \left({1 - \theta _2 /2} \right)^{r_2 - 1}} \right] $$\end{document} with \documentclass{article}\pagestyle{empty}\begin{document}$ \theta _i = \left({1/\beta} \right)\int_{T_0}^T {\kappa _i dT \le r_i} $\end{document} dT ≤ ri and ri = 1/(1-ni).Fitting this equation to the DSC response measured at a scan rate of 4°C/min obtains p ≈ 0.66; n1 ≈ 0.55; n2 ≈ 2.2; B1 ≈ 8285; B2 ≈ 7480; κ1 ≈ 1. 12 × 108 s-1; κ2 ≈ 0.99 × 106 S-1.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pen.760312306
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