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The reactions of N-methylformamide and N,N-dimethylformamide with OH and their photo-oxidation under atmospheric conditions: Experimental and theoretical studies
The reactions of OH radicals with CH3NHCHO (N-methylformamide, MF) and (CH3)2NCHO (N,N-dimethylformamide, DMF) have been studied by experimental and computational methods. Rate coefficients were determined as a function of temperature (T = 260-295 K) and pressure (P = 30-600 mbar) by the flash photolysis/laser-induced fluorescence technique. OH radicals were produced by laser flash photolysis of 2,4-pentanedione or tert-butyl hydroperoxide under pseudo-first order conditions in an excess of the corresponding amide. The rate coefficients obtained show negative temperature dependences that can be parameterized as follows: kOH+MF = (1.3 ± 0.4) × 10-12 exp(3.7 kJ mol-1/(RT)) cm3 s-1 and kOH+DMF = (5.5 ± 1.7) × 10-13 exp(6.6 kJ mol-1/(RT)) cm3 s-1. The rate coefficient kOH+MF shows very weak positive pressure dependence whereas kOH+DMF was found to be independent of pressure. The Arrhenius equations given, within their uncertainty, are valid for the entire pressure range of our experiments. Furthermore, MF and DMF smog-chamber photo-oxidation experiments were monitored by proton-transfer-reaction time-of-flight mass spectrometry. Atmospheric MF photo-oxidation results in 65% CH3NCO (methylisocyanate), 16% (CHO)2NH, and NOx-dependent amounts of CH2NH and CH3NHNO2 as primary products, while DMF photo-oxidation results in around 35% CH3N(CHO)2 as primary product and 65% meta-stable (CH3)2NC(O)OONO2 degrading to NOx-dependent amounts of CH3NCH2 (N-methylmethanimine), (CH3)2NNO (N-nitroso dimethylamine) and (CH3)2NNO2 (N-nitro dimethylamine). The potential for nitramine formation in MF photo-oxidation is comparable to that of methylamine whereas the potential to form nitrosamine and nitramine in DMF photo-oxidation is larger than for dimethylamine. Quantum chemistry supported atmospheric degradation mechanisms for MF and DMF are presented. Rate coefficients and initial branching ratios calculated with statistical rate theory based on molecular data from quantum chemical calculations at the CCSD(T?)-F12a/aug-cc-pVTZ//MP2/aug-cc-pVTZ level of theory show satisfactory agreement with the experimental results. It turned out that adjustment of calculated threshold energies by 0.2 to 8.8 kJ mol-1 lead to agreement between experimental and predicted results.
Bunkan, Arne Joakim C.,Hetzler, Jens,Mikoviny, Tomá?,Wisthaler, Armin,Nielsen, Claus J.,Olzmann, Matthias
p. 7046 - 7059
(2015)
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LIF spectra of n-propoxy and i-propoxy radicals and kinetics of their reactions with O2 and NO2
Fluorescence excitation spectra of CH3CF2CH2O (n-propoxy) and (CH3)2CHO (i-propoxy) radicals were obtained using a combined laser photolysis/laser-induced fluorescence (LIF) technique and the kinetics of reactions of these radicals with (1) O2 as a function of temperature and with (2) NO2 as a function of pressure have been determined. Propoxy radicals were produced by excimer laser photolysis of the appropriate propyl nitrites at γ=351 nm. The spectra of the (A?←X?) transitions show progressions of the CO-stretching vibration in the electronically excited states with spacings of the bands of (560±10)cm-1 for i-propoxy and (580±10)cm-1 for n-propoxy. Fluorescence spectra taken after excitation in the (4,0) band at λ=340.1 nm (i-propoxy) and in the (1,0) band at λ=342.4 nm (n-propoxy) show progressions of the CO-stretching vibration in the electronic ground state of (900±60) cm-1 for i-propoxy and (1000±50) cm-1 for n-propoxy. The Arrhenius expressions for the ractions of n-propoxy and i-propoxy with O2 have been determined to be k1 (n) = (1.4±0.6)×10-14 exp (-(0.9±0.5) kJ mol-1/RT) cm3 s-1 and kt (i) = (1.0±0.3)×10-14 exp (-(1.8±0.4) kJ mol-1/RT) cm3 s-1 in the range 218-313 K. The rate coefficients for the reactions of NO2 with n-propoxy and i-propoxy at T=296 K were found to be independent of total pressure with k2(n)=(3.6±0.4)×10-14 cm3 s-1 (6.7-53 mbar) and k2(i)=(3.3±0.3)×10-11 cm3 s-1 (6.7-106 mbar). WILEY-VCH Verlag GmbH, 1998.
Mund,Fockenberg,Zellner
p. 709 - 715
(1998)
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Highly efficient hydroxylation of gaseous alkanes at reduced temperature catalyzed by cytochrome P450BM3 assisted by decoy molecules
Cytochrome P450BM3 functions as a small-alkane hydroxylase upon the addition of perfluorocarboxylic acids (PFs) as decoy molecules. The coupling efficiency (product formation rate per NADPH consumption rate) for the hydroxylation of small alkanes was improved by reducing the reaction temperature to 0°C.
Kawakami, Norifumi,Cong, Zhiqi,Shoji, Osami,Watanabe, Yoshihito
p. 329 - 334
(2015/05/13)

A mild and practical synthesis of biphenyl compounds
A mild and practical synthetic route for biphenyls is established. Isopropyl nitrite was prepared from sodium nitrite, isopropanol and hydrochloric acid. The biphenyl compounds were obtained from the diazotisation of aniline derivatives with the generated isopropyl nitrite and the coupling reaction with benzene derivatives in the presence of CuCl as a catalyst in good yields.
Liang, Shuang,Cao, Xiaohui,Yan, Xilong,Chen, Ligong
p. 555 - 556
(2012/10/29)

Use of perfluorocarboxylic acids to trick cytochrome P450BM3 into initiating the hydroxylation of gaseous alkanes
It has long been believed that the fatty acid hydroxylase wild-type P450BM3 is unable to oxidize gaseous alkanes. However, the simple addition of a perfluorocarboxylic acid as a dummy substrate to initiate the P450BM3 catalytic cycle enabled the efficient hydroxylation of butane and propane (see picture).
Kawakami, Norifumi,Shoji, Osami,Watanabe, Yoshihito
supporting information; experimental part
p. 5315 - 5318
(2011/07/09)

Process for producing nitrite
A process for producing a nitrite includes allowing a nitrogen oxide to react with an alcohol at a reaction temperature lower than 10° C.
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(2009/03/07)

NEW METHOD FOR THE MANUFACTURE OF THERAPEUTIC COMPOUNDS AND COMPOSITIONS, COMPOUNDS AND COMPOSITIONS PRODUCED THEREWHITH, AND THEIR USE
Organic nitrites can be produced from a compound which is a mono/polyhydric alcohol or an aldehyde- or ketone-derivate thereof after de-aeration of the same, using NO gas, and stored in an environment saturated with gaseous NO. Organic nitrites produced according to the invention exhibit less impurities and improved storage stability compared to conventionally produced nitrites. The organic nitrites of the invention can easily be formulated into pharmaceutical compositions and have utility for the treatment of various conditions.
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(2008/06/13)

Gas phase kinetics of the reaction system of 2NO2 ? N 2O4 and simple alcohols between 293-358 K
The reversible reactions between nitrogen dioxide and alcohols (CH 3OH, CH3CH2OH, CH3CH 2CH2OH, CH3CHOHCH3) have been studied in the gas phase, using the spectrophotometric method. RONO (R = CH 3, CH3CH2, CH3CH2CH 2, CH3CHCH3) were identified by UV spectra. The equilibrium constants as well as the bimolecular rate constants were determined by computer modeling, using the programme MINICHEM. We calculated the following values for the forward rate constants k3av: (3.0±0.9)×10-18, (8.0±2.4)×10 -18, (5.4±1.6)×10-18, (2.0±0.6) ×10-18 cm3 molec-1 s-1 and the equilibrium constants Kav: 100±30, 40±12, 109±33, 39±12 at 298 K for the reactions with methanol, ethanol, 1-propanol and 2-propanol, respectively. The temperature dependence of the rate constants and the equilibrium constants were studied and it allowed to obtain the activation energy for the forward and for the reverse reaction, as well as thermochemical parameters. The equilibrium constants and the rate constants suggest that symmetrical N2O4 is the reactive species.
Wojcik-Pastuszka,Gola,Ratajczak
p. 1301 - 1313
(2007/10/03)

Dispersed fluorescence spectroscopy of primary and secondary alkoxy radicals
Dispersed fluorescence (DF) spectra of 1-propoxy, 1-butoxy, 2-propoxy, and 2-butoxy radicals have been observed under supersonic jet cooling conditions by pumping different vibronic bands of the B-X laser induced fluorescence excitation spectrum. The DF spectra were recorded for both conformers of 1-propoxy, three conformers of the possible five of 1-butoxy, the one possible conformer of 2-propoxy, and two conformers of the possible three of 2-butoxy. Analysis of the spectra yields the energy separations of the vibrationless levels of the ground X and low-lying A electronic state as well as their vibrational frequencies. In all cases, the vibrational structure of the DF spectra is dominated by a CO stretch progression yielding the vco stretching frequency for the X state and in most cases for the A state. In addition to the experimental work, quantum chemical calculations were carried out to aid the assignment of the vibrational levels of the X state and for some conformers the A state as well. Geometry optimizations of the different conformers of the isomers were performed and their energy differences in the ground states were determined. The results of the calculation of the energy separations of the close-lying X and A states of the different conformations are provided for comparison with the experimental observations.
Jin, Jin,Sioutis, Ilias,Tarczay, Gyoergy,Gopalakrishnan, Sandhya,Bezant, Andrew,Miller, Terry A.
p. 11780 - 11797
(2008/01/27)

Atmospheric fate of alkoxy radicals: Branching ratio of evolution pathways for 1-propoxy, 2-propoxy, 2-butoxy and 3-pentoxy radicals
As the last step of VOC oxidation in the atmosphere, the evolution of alkoxy radicals determines the nature and the concentration of the secondary compounds formed. Branching ratios between decomposition and reaction with O2 of 1-propoxy, 2-propoxy, 2-butoxy, and 3-pentoxy radicals were measured at room temperature and 1 atm in a simulation chamber using FTIR spectroscopy as an analytical device. The ratio varied depending on the leaving alkyl group and the class of alkoxy. No additional decomposition due to excited radicals was observed. The results could be used directly for tropospheric simulation purposes. Formaldehyde might be a photolytic source of HOx through the production of H and HCO radicals and acetaldehyde is the key precursor of the toxic NOx reservoir, peroxy-acetyl nitrate. In the lower troposphere, 1-propoxy and 2-propoxy radicals react mainly with O2 while decomposition is an important reaction pathway for 2-butoxy and 3-pentoxy. Consequently, C1 and C2 aldehyde production from the two longer chain alkoxys will occur very close to the area of initial VOC oxidation, while for the alkoxys exhibiting a minor decomposition pathway, the formaldehyde or acetaldehyde production will take place after oxidation of all the intermediate secondary compounds, far from the emission area of the primary compound.
Meunier,Doussin,Chevallier,Durand-Jolibois,Picquet-Varrault,Carlier
p. 4834 - 4839
(2007/10/03)

Rate constants for the reactions of C2H5O, i-C3H7O, and n-C3H7O with NO and O2 as a function of temperature
The rate constants of the reactions of ethoxy, i-propoxy and n-propoxy radicals with O2 and NO was investigated as function temperature. The radicals were generated by laser photolysis from the appropriate alkyl nitrite and characterized by laser-induced fluorescence. For the reactions with O2, the ethoxy radical reacted somewhat slower than recently recommended. The values obtained for i- and n-propoxy had been combined with the measurements from a recent study at lower temperatures, allowing a more reliable determination of the Arrhenius parameters.
Fittschen,Frenzel,Imrik,Devolder
p. 860 - 866
(2007/10/03)

Reaction of naphthalene and its derivatives with hydroxyl radicals in the gas phase
Naphthalene is the most abundant polycyclic aromatic hydrocarbon (PAH) found in urban air. It is reactive in the atmosphere under ambient conditions, its chief reaction partner being the hydroxyl radical, OH·. In this work, the reactions of OH· with naphthalene, 1- and 2-naphthol, and 1- and 2-nitronaphthalene were studied in a 9.4 m3 smog chamber. Relative rates of reaction accorded well with previous studies and allowed estimates to be made of the atmospheric lifetimes of these compounds. Numerous oxidation products were identified, and mechanisms proposed for their formation were based on the further transformation of benzocyclohexadienyl radicals formed by addition of OH· to naphthalene. The naphthols and nitronaphthalenes were deduced not to be on the major reaction pathway to the more oxidized products. Because of the high reactivity of PAH in air, we suggest that priority be given to identifying and quantitating their reaction products, some of which may be relatively persistent air toxics. Naphthalene is the most abundant polycyclic aromatic hydrocarbon (PAH) found in urban air. It is reactive in the atmosphere under ambient conditions, its chief reaction partner being the hydroxyl radical, OH·. In this work, the reactions of OH· with naphthalene, 1- and 2-naphthol, and 1- and 2-nitronaphthalene were studied in a 9.4 m3 smog chamber. Relative rates of reaction accorded well with previous studies and allowed estimates to be made of the atmospheric lifetimes of these compounds. Numerous oxidation products were identified, and mechanisms proposed for their formation were based on the further transformation of benzocyclohexadienyl radicals formed by addition of OH· to naphthalene. The naphthols and nitronaphthalenes were deduced not to be on the major reaction pathway to the more oxidized products. Because of the high reactivity of PAH in air, we suggest that priority be given to identifying and quantitating their reaction products, some of which may be relatively persistent air toxics.
Bunce, Nigel J.,Liu, Lina,Zhu, Jiang,Lane, Douglas A.
p. 2252 - 2259
(2007/10/03)

Nitrosation by Alkyl Nitrites. Part 5. Kinetics and Mechanism of Reactions in Acetonitrile
Simple alcohols and thioglycolic acid react with alkyl nitrites and nitrous acid in acidic acetonitrile solution to give the O- and S-nitrosated products, in reactions which are kinetically zero order in the alcohol or thiol concentration.The results are consistent with rate-liminiting NO+ formation.On addition of the parent alcohol (derived from the alkyl nitrite) reactions are slower and there is a change towards a first order dependence upon the substrate concentration, indicating that under these conditions the reaction of NO+ with the substrate is partly rate limiting.The reactivity order is found to be HNO2 > t-butyl-nitrite > i-propyl nitrite > isopentyl nitrite.Similarly aromatic amines yield nitrosamine or diazonium ion products, but now the kinetics are consistent with rate-limiting attack of NO+ with the unprotonated amine.At higher acidities it is proposed that reaction occurs with the protonated form of the amine.The mechanistic implications of the kinetic results are discussed.
Crookes, Michael J.,Williams, D. Lyn H.
p. 1319 - 1322
(2007/10/02)

A Versatile Synthesis of 1,1-Dioxo 7-Substituted Cephems: Preparation of the Human Leukocyte Elastase (HLE) Inhibitor 1,1-Dioxo-trans-7-methoxycephalosporanic Acid tert-Butyl Ester
A four-step synthesis of the human leukocyte elastase (HLE) inhibitor 1,1-dioxo-trans-7-methoxycephalosporanic acid tert-butyl ester in 44percent isolated yield from 7-aminocephalosporanic acid (7-ACA) is described.A variety of 7-substituents have been introduced via metal-catalyzed diazo insertion reactions, and the use of a flow reactor for chemodiscriminate control of particularly rapid reactions is presented.A chemoselective oxidation of 7-ACA tert-butyl ester to the corresponding 1,1-dioxide without formal N-protection is introduced.
Blacklock, Thomas J.,Butcher, John W.,Sohar, Paul,Rothauser Lamanec, Theresa,Grabowski, Edward J. J.
p. 3907 - 3913
(2007/10/02)

Nitrosation by Alkyl Nitrites. Part 2. Kinetics of Reactions in Aqueous Acid Solution with Isopropyl and t-Butyl Nitrites
The rates of reaction of isopropyl nitrite with sulphamic acid, hydrazoid acid, thioglycolic acid, cysteine, N-methylaniline, and thiourea are markedly reduced by the addition of propan-2-ol.A detailed kinetic analysis of the results is as expected for a mechanism where hydrolysis of isopropyl nitrite occurs rapidly (and reversibly) and released nitrous acid effects nitrosation.The analysis yields values for the equilibrium constant for isopropyl nitrite hydrolysis and also for the rate constants for nitrous acid nitrosation (for a range of substrates), which are in good agreement with the literature values obtained by direct measurement.For t-butyl nitrite the extent of hydrolysis is so great (and the reaction is so rapid) that the kinetics are identical with those obtained using nitrous acid.Under most of the experimental conditions employed the rate-limiting step is the reaction of H2NO2+ with the substrate, but at high for the more reactive species, the rate-limiting step changes to that of hydrolysis of RONO.This is particularly true for the t-butyl nitrite, where it is easier for the nitrosation of the substrate by nitrous acid to compete with the re-nitrosation of the alcohol, since the rate of the latter reaction is much smaller for a tertiary alcohol than it is for a secondary alcohol.Further experimental measurements on the ROH + HNO2 -> RONO system, for both isopropyl and t-butyl nitrites, confirm these mechanistic ideas.
Crookes, Michael J.,Williams, D. Lyn H.
p. 1339 - 1344
(2007/10/02)

Rate-limiting NO+ Formation in Nitrosation Reaction in Acetonitrile
Acid-catalysed nitrosation of methanol, thioglycolic acid, and water in acetonitrile using alkyl nitrites or nitrous acid (except in the case of water), is kinetically zero order in the substrate, consistent with rate-limiting NO+ formation.
Crookes, Michael J.,Williams, D. Lyn H.
p. 571 - 572
(2007/10/02)

Reaction of alcohol with NO2 on a Cleaned Glass Surface
Formation of alkyl nitrite from alcohol and NO2 was very fast on a Pyrex glass surface cleaned with chromic acid mixture.The reaction was practically zero order with respect to NO2.The rate constant was (1.7 +/- 0.08)*10E-18 cm3*molecule-1*s-1 for methyl nitrile formation and the apparent activation energy was -53.5 kJ*mol-1.
Maeda, Yasuaki,Fujio, Yoshifumi,Munemori, Makoto
p. 2127 - 2130
(2007/10/02)

Formation of Organic Nitro-compounds in Flowing H2O2+NO2+N2+Organic Vapour Systems. Part 3.-Effects of O2 Addition on H2O2+NO2+N2+Alkane Systems
The effects of oxygen on the product distribution from the surface-initiated reactions in flowing mixtures of H2O2, NO2, N2 and RH, where RH=ethane, propane, n-butane and n-pentane, at 298 K have been studied.In the absence of O2, the principal products are the corresponding nitroalkane, alkyl nitrite and alkyl nitrate.In the presence of sufficiently large concentrations of O2, the predominant product is the alkyl nitrate and the only other products of significance, in some cases, are the corresponding carbonyl compounds.The variation of the product yields with / gives values for the rate-constant ratios k8/(k3+k4) for reaction at both primary and secondary radical sites:.Possible mechanisms by which the products are formed are discussed.
Baulch, Donald L.,Campbell, Ian M.,Chappel, Jonathan M.
p. 617 - 628
(2007/10/02)

Formation of Organic Nitro-compounds in Flowing H2O2+NO2+N2+Organic Vapour Systems. Part 2.-H2O2+NO2+N2+Alkane System
The principal products from the surface-initiated reactions in flowing mixtures of H2O2, NO2,N2 and RH, where RH=ethane, propane, n-butane and n-pentane, have been identified as the nitroalkane, alkyl nitrite and alkyl nitrate.The product yields have been measured; in the case of propane the variation of the yields with total gas pressure has also been studied.Values have been obtained for the relative rates of primary and secondary H-atom abstraction from each alkane by OH and for the rate-constant ratios k3/k4 and k5/k6 at 298 K:.The trends in the product yields with the variation of pressure and change of R indicate that RO radicals are produced via reactions (4)-(6) rather than by a single-step reaction of R with NO2.
Baulch, Donald L.,Campbell, Ian M.,Chappel, Jonathan M.
p. 609 - 616
(2007/10/02)

A kinetic study of the influence of alcohols on the nitrosation of morpholine in acid media. Equilibrium constants for the formation of alkyl nitrites
The effect of the aliphatic alcohols methanol, ethanol, propanol, isopropanol, 2-butanol, isobutanol, and tert-butanol on the rate of nitrosation of morpholine at pH 3 and 25 deg C has been studied.The inhibition observed is attributed to the formation of alkyl nitrites, which are poor nitrosating agents in acid media.The equilibrium constants for the formation of alkyl nitrites from nitrous acid and alcohols have been calculated both spectrophotometrically and from kinetic data for the inhibitory effect, and there is agreement between the two sets of results.The molar absorptivities at 265 nm of the alkyl nitrites have also been determined.When the concentration of alkyl nitrite is very low, a slight catalytic effect considered to be an effect of the medium has been observed.
Casado, Julio,Lorenzo, Francisco Manuel,Mosquera, Manuel,Prieto, Maria Flor Rodriguez
p. 136 - 138
(2007/10/02)

Hydrolysis, Nitrosyl Exchange, and Synthesis of Alkyl Nitrites
Alkyl nitrites undergo relatively slow hydrolysis in phosphate-buffered aqueous media under neutral conditions with small but significant dependence of reactivity on structure.However, rapid nitrosyl exchange with alcohols is observed, and equilibrium constants for this transformation exhibit remarkable correlation with equilibrium constants for nitrosyl exchange of alcohols with nitrosyl chloride and with nitrous acid. tert-Butyl nitrite has the greatest driving force for nitrosyl transfer among the 12 alkyl nitrites examined, and this capability is used for the synthesis of alkyl nitrites derived from steroidal alcohols and of alkyl thionitrites.
Doyle, Michael P.,Terpstra, Jan W.,Pickering, Ruth A.,LePoire, Diane M.
p. 3379 - 3382
(2007/10/02)

Kinetics and Mechanism of the Nitrosation of Alcohols, Carbohydrates, and a Thiol
Rate constants have been determined by stopped-flow spectrometry for the nitrosation in water of the following alcohols and carbohydrates: methanol, ethanol, propan-l-ol, propan-2-ol, ethane-1,2-diol, propane-1,2,3-triol, mannitol, sucrose, and glucose, in some cases at 25o and others at 0o.In all cases the reactions were reversible, forming equilibrium concentrations of the corresponding alkyl nitrites.With a large excess of the alcohol present over the total nitrous acid concentration, the observed first order rate constants increased linearly with the alcohol concentration, and from the slope and the intercept the rate constants of the forward and reverse reactions were obtained.Both reactions were acid catalysed and also catalysed by chloride and bromide ion.The forward reaction is interpreted as one involving O-nitrosation by H2NO2+ (or NO+), NOCl or NOBr.For methanol, rate constants for attack by nitrosyl chloride and by nitrosyl bromide were 2.1 x 105 mol-1s-1, respectively.There was little difference between the rate constants for chloride ion and bromide ion attack for the reverse reaction, suggesting that the reactions for attack on the protonated alkyl nitrite are very rapid, possibly approaching the diffusion-controlled limit.There was a decrease in the overall equilibrium constant for the non-halide ion-catalysed pathway, along the series MeOH, EtOH, PriOH, and ButOH; the value for the latter was so small as to make the quantitative determination of the rate constants impossible by this method.This decrease was due almost entirely to a decreasing value for the forward rate constant along the series, which implies that a steric effect is operational.All the carbohydrates studied had very similar equilibrium constants of ca. 1.5.In contrast the nitrosation of N-acetylpenicillamine gave the thionitrite quantitatively at low acidities.Again the reaction was acid- and halide (and thiocyanate) ion-catalysed and the reactivity sequence NOCl > NOBr > NOSCN was established.For both the alcohols and the thiol, the forward rate constants are well below the diffusion controlled values and are several powers of ten less than the corresponding values for the reactions of aniline.The results are discussed in terms of the nucleophilicities of the oxygen and sulphur sites for the forward reaction and in terms of the protonation equilibria of the nitrites and thionitrite for the reverse reaction.
Aldred, S. Elaine,Williams. D. Lyn H.,Garley, Michael
p. 777 - 782
(2007/10/02)

Photochemical Studies of Nitromethane in Solution. III. Nitromethane in Isopropyl Alcohol
Photolysis of nitromethane in isopropyl alcohol solution at λ = 254 nm and λ >/= 290 nm has been investigated.In the reaction mixture besides the products found by other authors 2-hydroxy-2-propyl azodioxymethane and pinacol have also been found.Quantum yields of some photoproducts formation have been determined.The photochemical reaction of cis and trans nitrosomethane dimers, probably the main products in the investigated system, have been examined in isopropanol alcohol solution at 254 nm and 313 nm.The reaction mechanism has been proposed and discussed.
Kozubek, Halina,Paszyc, Stefan
p. 481 - 488
(2007/10/02)