Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Volume 55 , Issue 12
Showing 1-50 articles out of 64 articles from the selected issue
  • Akio Furusaki, Nobuhiro Hashiba, Takeshi Matsumoto, Atsushi Hirano, Yu ...
    1982 Volume 55 Issue 12 Pages 3681-3685
    Published: 1982
    Released: June 27, 2006
    JOURNALS FREE ACCESS
    The molecular sturcture of staurosporine, an alkaloid from a Streptomyces strain, has been determined by means of an X-ray crystallographic analysis of its methanol solvate (C28H26N4O3·CH3OH). The crystals are monoclinic, with four formula units in a unit cell with dimensions of a=23.487(6), b=7.636(3), c=15.638(4) Å, and β=116.71(5)°; the space group is C2. 2532 unique intensity data were collected on a four-circle diffractometer with LiF-monochromated Cu Kα radiation. The structure was solved by the Monte Carlo direct method, using the 20 strongest reflections as the starting set; the 72nd random phase set led to the correct solution. The R value reached 0.047 by block-diagonal least-squares refinements. Staurosporine has been found to contain a unique dimeric indole structure. Because of the steric hindrance, the indolo[2,3-a]carbazole aromatic system in the molecule is slightly bent; the two terminal benzene rings make an angle of 7.5° with each other.
  • Yashige Kotake, Keiji Kuwata
    1982 Volume 55 Issue 12 Pages 3686-3689
    Published: 1982
    Released: June 27, 2006
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    The nature of the intramolecular hydrogen bond in hydroxysubstituted nitroxide radicals was examined. The hydroxysubstituted radical was produced by the spin trapping reaction of hydroxyalkyl radicals with α-phenyl-N-t-butylnitrone. The magnitude of the hyperfine splitting caused by β-hydrogen of the radical is strongly dependent on the composition of the solvent, which is attributed to the formation of the intramolecular hydrogen bond. The equilibrium constant of the intramolecular hydrogen bond in an aprotic solvent was determined by observing the magnitude of the hyperfine splitting of β-hydrogen as a function of the amount of added methanol. Based on the temperature dependence of the equilibrium constant, the standard entropy and the standard enthalpy of the formation of the hydrogen-bonded chelate ring was estimated. The same method of analysis was applied to the system of diastereomeric nitroxide and the difference of the internal energy of the chelate ring in the isomers was detected. Moreover, the difference was utilized to separate the ESR spectra of the diastereomers.
  • Hiroshi Suzuki, Kinko Koyano, Tadamasa Shida, Akira Kira
    1982 Volume 55 Issue 12 Pages 3690-3701
    Published: 1982
    Released: June 27, 2006
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    The electronic absorption spectra of radical ions produced by γ-ray irradiation of (E)-stilbene and related compounds in frozen matrices were measured. On illumination and on controlled warming, the spectra of the radical ions of sterically uncrowded stilbenes and diphenylacetylene remained almost unchanged, while those of the radical ions of sterically crowded stilbenes changed noticeably. Examination of the spectra and of their changes led to the following conclusions: (a) The relaxed geometry of the radical ions of sterically uncrowded stilbenes is planar or nearly planar; (b) in the unrelaxed geometries of the radical ions of (E)-α,β-dialkylstilbenes the torsion angles of the Ph–C bonds are nearly as large as in the parent molecules, and on relaxation these angles become smaller and the torsion angle of the central ethylenic bond deviates from 0° to a considerable extent; (c) for the radical ions of ortho-substituted (E)-stilbenes the geometrical change on relaxation is comparatively small.
  • Masako Yamamoto, Takayuki Sano, Shoji Harada, Tatsuya Yasunaga
    1982 Volume 55 Issue 12 Pages 3702-3706
    Published: 1982
    Released: June 27, 2006
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    Kinetic studies of the amylose–iodine complex formation for the amylose of degree of the polymerization (DP) of 32 were made using the temperature-jump method. The reciprocal relaxation time increases with increase of the concentration of iodine and decreases with that of amylose. Based on these results, the reaction, H0+3I3\ ightleftharpoonsH3 was proposed as a plausible mechanism for the relaxation phenomenon, where H0 denotes the free helical segment of amylose and H3 the helical segment containing three I3. The relaxation phenomena were observed for the amyloses of DP 42, 57, and 76, and analyzed by the same mechanism as that proposed in the case of DP 32. The rate constants for the forward and the backward reactions (kf and kb) were determined: the kf value increases with DP of amylose and the kb value decreases. Examination of the relaxation time and the relaxation amplitude suggested that the relaxation phenomenon is not based on the whole process of the amylose–iodine complex formation but on the H3 complex formation reaction which was shown to be the nucleation process.
  • Minoru Fukui, Yoshio Matsunaga
    1982 Volume 55 Issue 12 Pages 3707-3710
    Published: 1982
    Released: June 27, 2006
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    By the addition of 4,4′-dinitrobiphenyl to nonmesogenic 4-(dimethylamino)-4-alkoxy derivatives of N-benzylideneaniline, smectic liquid crystals could be induced. This dinitro compound induces liquid crystals more pronouncedly than N-(4-nitrobenzylidene)-4-nitroaniline and 4,4′-dinitroazoxybenzene do when the alkoxyl group in the donor molecule is methoxyl or ethoxyl, while it induces less pronouncedly when the alkoxyl group is propoxyl. 4,4′-Dicyanobiphenyl gives a metastable nematic liquid crystal when it is mixed with N-[4-(dimethylamino)benzylidene]-4-propoxyaniline and a metastable smectic liquid crystal with N-(4-propoxybenzylidene)-4-(dimethylamino)aniline. Moreover, liquid crystals are formed in the binary systems of N,N,N′,N′-tetramethylbenzidine with 4-nitro-4-alkoxy derivatives of N-benzylideneaniline. They are metastable but cover rather wide composition ranges. The examination of the layer spacing of the smectic A phase revealed that the induced phase is a monolayer liquid crystal.
  • Kazuhiko Seki, Yoshio Imamura
    1982 Volume 55 Issue 12 Pages 3711-3716
    Published: 1982
    Released: June 27, 2006
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    In poly(1-vinylnaphthalene)(P1VN) and poly(2-vinylnaphthalene)(P2VN), conformational energies of meso and racemic dyads were computed as functions of skeletal bond and side group rotations (0°(o) or 180°(π)). The calculation was carried out according to the truncation procedure proposed by D.Y.Yoon. The backbones in P1VN and P2VN were limited to just two rotational states, trans (t) and gauche (g) conformation. The steric interactions involving the bulky naphthyl group precluded \barg conformation; a similar situation occurs in polystyrene. Numerical results suggested these conclusions: the excimer forming site conformations for P1VN were meso : tt(ππ) and racemic : tt(ππ) states, and for P2VN were meso : tt(ππ), tt(oo), tt(oπ), and tt(πo) states. These conformations could also be correlated to the dual emissions observed in P1VN and P2VN.
  • Tsunetaka Sasaki, K\={o}ji Mochizuki, Satoshi Ishiwata
    1982 Volume 55 Issue 12 Pages 3717-3719
    Published: 1982
    Released: June 27, 2006
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    The macromolecular ion flotation of Fe3+, Cu2+, and Ni2+ ions by the combined use of charcoal and hexadecyltrimethylammonium chloride (HTAC) was studied. The flotation of powdered active charcoal itself was first studied; a 100% floatability was obtained for the flotation of 2500 ppm charcoal by the addition of 6 ppm of polyacrylamide and 550 ppm of HTAC in the pH range from 4 to 13. For the studies of the flotation of Fe3+, Cu2+, and Ni2+ ions, diagrams of the floatability of the respective ions vs. the composition of charcoal and HTAC, and the floatability of the respective ions vs. the pH at a constant composition of charcoal and HTAC, were constructed. A nearly 100% floatability was obtained for Fe3+, Cu2+, and Ni2+ ions at pH values larger than 4.5, 9.5, and 11 respectively. This order is the same as that of the solubility products of Fe(OH)3, Cu(OH)2, and Ni(OH)2. It was confirmed that Fe3+ ions are adsorbed as hydroxides on charcoal; they are subsequently floated over the whole range of pH values combined with charcoal, while the Cu2+ and Ni2+ ions are adsorbed as simple ions on charcoal and floated in the lower pH region. They are adsorbed as hydroxide on charcoal and floated in a higher pH region.
  • Toshifumi Watanabe, Takeshi Kyogoku, Shigeru Tsunashima, Shin Sato, Sh ...
    1982 Volume 55 Issue 12 Pages 3720-3723
    Published: 1982
    Released: June 27, 2006
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    The absolute rate constants of the addition of H and D atoms to propylene-d0 and -d6 have been measured by means of the pulse radiolysis-resonance absorption technique over the temperature range of 200–500 K. The rate constants obtained were well expressed by these Arrhenius equations: k(H+C3H6)=(3.00±0.38)exp[−(1612±66)⁄RT], k(H+C3D6)=(2.55±0.57)exp[−(1509±128)⁄RT], k(D+C3H6)=(1.99±0.05)exp[−(1550±15)⁄RT], and k(D+C3D6)=(2.20±0.27)exp[−(1587±67)⁄RT] in units of 10−11 cm3 molecule−1 s−1. The unit of activation energy is cal mol−1. Practically no isotope effects attributable to the difference between C3H6 and C3D6 could be observed. This is similar to the kinetic isotope effects previously observed in the rate constants of the addition of H and D atoms to isotopic ethylenes. The theoretical rate constants of the above reactions have been calculated by the conventional activated complex theory using the potential energy surface drawn by the ab initio method; however, no agreement with regard to the isotope effects could be obtained between experiment and theory because of the difference between C3H6 and C3D6. This also is similar to the isotope effects found in the H+C2H4→C2H5 reaction.
  • Satoshi Inagaki, Hirofumi Kawata, Yoshio Hirabayashi
    1982 Volume 55 Issue 12 Pages 3724-3732
    Published: 1982
    Released: June 27, 2006
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    The orbital phase continuity-discontinuity property is shown to control electron delocalization and polarization even in open chain conjugated molecules. Its chemical consequences are discussed.
  • Kimio Isa, Hiroki Okuno
    1982 Volume 55 Issue 12 Pages 3733-3737
    Published: 1982
    Released: June 27, 2006
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    Dehydration of calcium sulfate dihydrate was studied by means of simultaneous TG-DTG-DTA under various sealed atmospheres corresponding to three systems open, completely sealed, and quasi-sealed. Two dehydration steps could be detected under self-generated atmospheres by using 12.3, 18.7, 30.0, and 250 μm tungsten wires. This new method enables us to identify intermediates more easily than any other techniques hitherto adopted. Endothermic DTA peaks appeared earlier, at 129 and 133 °C, than the point of decreasing TG. This technique, resembling the quasi-isothermal and -isobaric thermogravimetry (Q-TG), is superior to Q-TG in that it requires smaller amounts of sample.
  • Yutaka Fukuda, Hiroko Kimura, Kozo Sone
    1982 Volume 55 Issue 12 Pages 3738-3741
    Published: 1982
    Released: June 27, 2006
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    The visible absorption spectra of three new mixed chelates of copper(II), Cu(acac)(tmen)X (acac=acetylacetonate ion, tmen=N,N,N′,N′-tetramethylethylenediamine, and X=Cl, Br, or I) were studied in various organic solvents. The \ ildeνmax values of their d-d bands depend strongly on the nature of the solvent, similarly to the pseudohalide complexes reported in the preceding paper. These data show the existence of the equilibrium:
    [Cu(acac)(tmen)X]\ ightleftharpoons[Cu(acac)(tmen)]++X
     (5-coordinated) (4-coordinated, with axial solvation)
    in such solutions, which is shifted to the right hand side with increase of the solvent polarity and with decrease of the coordination ability of the X anion, i.e., in the order Cl→Br→I.
  • Takashi Shibahara, Shun’ichiro Ooi, Hisao Kuroya
    1982 Volume 55 Issue 12 Pages 3742-3746
    Published: 1982
    Released: June 27, 2006
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    The μ-oxo-μ-sulfido-(oxalato)molybdate(V) complex has been prepared and characterized by X-ray analysis. The potassium salt crystallizes in monoclinic system, space group C2/c, with cell dimensions a=13.640(3), b=20.296(3), c=15.213(4) Å, β=106.42(2)°, and Z=4. The structure was solved by the heavy-atom technique and refined by the block-diagonal least-squares method to R=0.048 for 3552 independent reflections. The complex anion is tetrameric, two dimeric Mo2O3S(ox)2 moieties being bridged by one oxalato ligand. Both the molybdenum atoms in the dimer are bridged by one sulfur and one oxygen atoms. Each molybdenum atom has distorted octahedral environment; two oxygen atoms of a bidentate oxalato ligand, bridging sulfur and oxygen atoms in the equatorial plane, a terminal oxygen and one of the bridging quadridentate oxalato ligand oxygens. The complex can be denoted as K6[{Mo2O3S(ox)2}2(ox)]·10H2O and has an approximate C2h symmetry, with a crystallographic center of symmetry. The Mo–O (quadridentate bridging oxalato) bonds (2.304(4), 2.302(4) Å) are evidently longer than the Mo–O (bidentate oxalato) bonds (2.112(4), 2.102(4), 2.093(4), 2.120(4) Å). The influence of the bridging oxalato ligand on the geometry of Mo2O3S core will be discussed.
  • Naoyasu Oishi, Masataka Takeuchi, Yuzo Nishida, Sigeo Kida
    1982 Volume 55 Issue 12 Pages 3747-3749
    Published: 1982
    Released: June 27, 2006
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    Some planar binuclear copper(II) complexes showed high catalytic activity for the chemiluminescence of luminol in the presence of hydrogen peroxide compared with those of mononuclear planar copper(II) complexes. The formation of singlet O2 in the reaction mixture of a binuclear copper(II) complex and hydrogen peroxide was assumed to play a key role in the catalytic function of the binuclear copper(II) complexes for the luminol chemiluminescence.
  • Hiroshi Kawaguchi, Mari Ishii, Tomoharu Ama, Takaji Yasui
    1982 Volume 55 Issue 12 Pages 3750-3756
    Published: 1982
    Released: June 27, 2006
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    Complexes of the [Co(tripeptidato)(NH3)2] and NH4[Co(tetrapeptidato)(NH3)2] types (tripeptidato and tetrapeptidato denote the tri- and tetraanions of the coordinating peptides respectively) have been prepared and characterized by means of their electronic, 1H NMR, and circular dichroism (CD) spectral data. In the NH4[Co(tetrapeptidato) (NH3)2] complex, the pep tide coordinates to cobalt(III) as a quadridentate ligand through the nitrogens of an amino and three amide groups. The additivity of the vicinal CD spectra has been found to hold for the complexes of a series of tripeptides containing L-alanine and/or glycine residue. These tri- and tetrapeptidato complexes in water easily undergo aquation reaction, releasing the ammonia molecule.
  • Masao Takahashi, Iwao Watanabe, Shigero Ikeda, Masato Kamata, Sei Otsu ...
    1982 Volume 55 Issue 12 Pages 3757-3759
    Published: 1982
    Released: June 27, 2006
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    Helium(I) ultraviolet photoelectron spectrum is reported for the compound Mo(t-BuS)4. The observed spectrum is interpreted by means of DV-Xα MO calculations on the model compounds Mo(SH)4 and Mo(SMe)4. The UV photoelectron spectrum of Mo(t-BuS)4 exhibits a low ionization potential band (IP=6.43 eV) which corresponds to ionization of mainly Mo4dz2 electron of A1 representation. This molecular orbital has also bonding character between Mo4d and S3d.
  • Yuzo Tamari, Yukiharu Inoue, Haruo Tsuji, Yuzuru Kusaka
    1982 Volume 55 Issue 12 Pages 3760-3765
    Published: 1982
    Released: June 27, 2006
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    The chemical composition of groundwaters from granitic alluvial plains is different from that from the clayey “Kobe-group” strata surrounding the Rokko mountains. The former groundwaters are dominantly rich in Ca and HCO3, while the latter are rich in Na and HCO3. In order to investigate the difference in the groundwater compositions, a chemical leaching technique was applied to samples of soils, well-sediments, and rocks collected from the Rokko mountains and their surroundings. Three leaching solutions used were as follows. CO2 saturated water to investigate the effect of chemical weathering; a 0.1 M HNO3 solution to remove hydroxide, sulfide, and colloidal matters; and a 1 M CH3COONH4 solution to leach exchangeable ions from the samples. In the leaching, leachable amounts of Na, K, Ca, and Mg as the major species and Fe and Mn as the minor species in groundwaters were determined. From the results of leaching and adsorption experiments for cations, and from a comparison of the analytical values of the cations in groundwaters with the data of the leaching experiments on the key diagram, the association of the chemical species dissolved in groundwaters with the geological characters was analysed.
  • Makoto Watanabe
    1982 Volume 55 Issue 12 Pages 3766-3769
    Published: 1982
    Released: June 27, 2006
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    The effect of cations on the rate of the hydrolysis of cyclo-tri- and cyclo-tetraphosphates was studied by adding metal chlorides to aqueous solutions of the ring phosphates. The concentrations of the phosphates and metal chlorides were 0.025 mol dm−3 and 0.1 mol dm−3 respectively. Alkali-metal cations retarded the hydrolysis of both the cyclo-phosphates in acidic media and accelerated it in basic media. The following sequence of efficiency resulted:
    Li+>Na+>K+.
    Magnesium, calcium, and nickel(II) cations retarded the hydrolysis of the cyclo-phosphates in the pH range of 1.0–2.0 or 1.0–2.7, while they accelerated it in the pH regions higher than 2.7 or 3.5. A copper(II) ion retarded the hydrolysis at pH 1.0, and accelerated it in the pH ranges higher than 2.0. An aluminium ion highly accelerated the hydrolysis of both the ring phosphates at pH 1.0 and 2.0.
  • Ryokichi Tsuchiya, Akira Uehara, Yoshinori Muramatsu
    1982 Volume 55 Issue 12 Pages 3770-3772
    Published: 1982
    Released: June 27, 2006
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    By measuring calorimetrically the heats of reaction of solid cis- and trans-[CoX2en2]X (X=Cl, Br) with alkaline sodium sulfide solution, the heats of isomerization were obtained as −11.4 kJ mol−1 for cis-[CoCl2en2]Cl(s)=trans-[CoCl2en2]Cl(s) and −6.4 kJ mol−1 for cis-[CoBr2en2]Br(s)=trans-[CoBr2en2]Br(s). Assuming the entropy changes from cis- to trans-form, ΔS, to be −0.0116 kJ mol−1 K−1 at 25 °C statistically, the free energy changes were calculated as ΔG°=8.0 kj mol−1 and −3.0 kJ mol−1 for the isomerization of cis-[CoCl2en2]Cl and cis-[CoBr2en2]Br respectively. From these thermodynamic data, cis-to-trans isomerization was expected to occur in [CoX2en2]X (X=Cl or Br), which was verified experimentally by thin-layer chromatography and the spectral measurement.
  • Tatsuya Sekine, Kazuho Inaba
    1982 Volume 55 Issue 12 Pages 3773-3777
    Published: 1982
    Released: June 27, 2006
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    The rate of the extraction of iron(III) in aqueous 4 mol dm−3 sodium perchlorate solutions with 1,1,1-trifluoro-2,4-pentanedione (Htfa) into carbon tetrachloride was measured, and the rate constants for the controlling reactions in the aqueous phase:
    Fe3++Htfa→Fe(tfa)2++H+and Fe(OH)2++Htfa→Fe(tfa)2++H2O,
    were calculated. These constants were also determined from spectrophotometric measurements of the aqueous solutions in the absence of the organic phase. The two series of rate constants obtained by the independent experiments agreed well. It was pointed out that equilibrium constants among the complexes in the aqueous and organic phases are indispensable in order to make a precise discussion of the solvent extraction of metal ions when aqueous-complex formation controls the whole process.
  • Akifumi Yamada, Yoshikiyo Kato, Yasuo Nakabayashi, Nobuyuki Tanaka
    1982 Volume 55 Issue 12 Pages 3778-3781
    Published: 1982
    Released: June 27, 2006
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    A modified technique for the potentiostatic method has been applied to the study on the outer-sphere association of some substitution-inert complex cations with sulfate ions. The association constants were determined from the change in limiting time as function of the concentration of sulfate ions at ionic strength 0.2 and 25 °C: 29±3 for [Co(NH3)6]3+–SO42−, 23±2 for [Co(en)3]3+–SO42−, 34±3 for [Co(H2O)(NH3)5]3+–SO42−, 18±2 for [Cr(NH3)6]3+–SO42−, 21±2 for [Cr(en)3]3+–SO42−, 19±2 for [Cr(H2O)(NH3)5]3+–SO42−, 13±2 for [Cr(urea)6]3+–SO42−. The ratios of the diffusion coefficient of the univalent ion pairs to that of tervalent substitution-inert complex cations were also obtained. From these ratios, the diffusion coefficients of the univalent ion pairs were calculated; these were found to be close to those of univalent complex ions with similar structures.
  • Yasushi Inoue, Hiromichi Yamazaki
    1982 Volume 55 Issue 12 Pages 3782-3788
    Published: 1982
    Released: June 27, 2006
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    A comprehensive study of the preparation of hydrous tin(IV) oxide ion-exchangers was made by using eight systems: (1)Na2[Sn(OH)6]–H2SO4, (2)Na2[Sn(OH)6]–H2SO4(boiling), (3)Na2[Sn(OH)6]–HCl, (4)Na2[Sn(OH)6]–CH3COOH, (5)SnCl4–NaOH, (6)SnCl4–NH3aq, (7)SnCl4–NH3aq(boiling), and (8)SnCl4-pyrohydrolysis. From a detailed examination of the dependency of the yield, the ion-exchange behavior toward Na+ and Cl ions, the composition, and some other properties on the conditions for precipitation, it was found that the ion-exchange characteristics are similar among materials produced from the systems from (1) through (7) if we neglect some aging effect of boiling, while the difficulty of synthesis differs according to the systems. The materials obtained from the (8) system, however, showed titration curves different from those for the exchanges obtained from the other systems and had less cation-exchange capacity for Na+ by 20 per cent. From these results, it is concluded that the simplicity of the synthetic procedures in the most important criterion for choosing the best conditions for preparing the exchanger.
  • Yuriko Abe, Goro Wada
    1982 Volume 55 Issue 12 Pages 3789-3794
    Published: 1982
    Released: June 27, 2006
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    The substitution reaction rates of hexamethylphosphoric triamide (HMPA) for NN (NN=2,2′-bipyridine (bpy), 4,4′-dimethyl-2,2′-bipyridine (dmbpy), or 1,10-phenanthroline (phen)) on tetrahedral complexes [Co(NN)(hmpa)2]2+ were determined spectrophotometrically in pure HMPA or in nitrobenzene, acetone, 1,2-dichloroethane, and nitromethane at various concentrations of HMPA, for the purpose of clarifying the reaction mechanism and the effect of the bulkiness of HMPA. The ligand substitution reaction on bpy and dmbpy complexes proceeds simply via a dissociative mechanism in nitrobenzene. In inert solvents other than nitrobenzene, it proceeds in parallel via two simultaneous paths of both dissociative and associative mechanisms. In the case of the phen complex, the reaction proceeds only by a dissociative mechanism in pure HMPA and in all the inert solvents used. The activation enthalpies and the activation entropies of the dissociative mechanism of bpy and dmbpy complexes were (80–90) kJ mol−1 and approximately zero J K−1 mol−1, respectively, in all the solvents used. Those for the phen complex were (86–101) kJ mol−1 and (−16–+36) J K−1 mol−1, respectively, while those of the associative mechanism for bpy and dmbpy complexes in all the solvents used except nitrobenzene were (50–65) kJ mol−1 and large negative values, respectively. Whether the substitution proceeds by the dissociative mechanism or by the associative one, both the steric and the solvent effects appear seriously, because HMPA is a bulky ligand and had a large dipole moment.
  • Tsutomu Sekine, Masanobu Sakanoue, Takashi Nakamura, Kenji Yoshihara
    1982 Volume 55 Issue 12 Pages 3795-3799
    Published: 1982
    Released: June 27, 2006
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    Chemical effects of the 59Co(γ,n)58m,gCo reaction and of the isomeric transition of 58mCo in Co(acac)3, Co(acac)2, and Co(acac)2·2H2O were studied by using a vacuum sublimation technique. In the isomeric transition, highly enriched 58gCo(acac)2 was separated from 58mCo(acac)3. By the (γ,n) reaction, about a half of the radioactive nuclides produced were found in the form of Co(acac)2 after irradiation of Co(acac)3. The present results were compared with those obtained by other authors.
  • Tadashi Hara, Kaoru Fujinaga, Fujio Okui
    1982 Volume 55 Issue 12 Pages 3800-3805
    Published: 1982
    Released: June 27, 2006
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    In order to clarify the effect of the coexistent elements on the determination of the atomic ratio between C, H, O, and N by the pyrolytic sulfurization gas chromatography (PSGC), compounds containing 25 kinds of elements were investigated. Only 7 of these interfered the determination of the atomic ratio. Several organophosphorus, lithium-, and boron-containing compounds were also analyzed. The results obtained by the present work are summarized in the periodic table together with those from previous work.
  • Kozo Sone, Haruo Ohashi
    1982 Volume 55 Issue 12 Pages 3806-3807
    Published: 1982
    Released: June 27, 2006
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    The X-ray structure of the CoO8 unit in cobalt garnet, a new synthetic silicate of the composition Co3Al2Si3O12, is presented. The unit can be taken as a deformed cube, but its central CoII is more regularly 8-coordinated than that in [Co(NO3)4]2− studied formerly by Bergman and Cotton. The electronic spectrum and magnetic moment of cobalt garnet are discussed in comparison with those of two other silicates containing CoO4 units.
  • Toshimi Shimizu, Yoshio Tanaka, Keishiro Tsuda
    1982 Volume 55 Issue 12 Pages 3808-3816
    Published: 1982
    Released: June 27, 2006
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    A bis(cyclic tetrapeptide), S,S′-bis[cyclo(Gly–L-hemiCys–Sar–L-Pro)] (BCGCSP), was prepared by coupling two homodetic cyclotetrapeptide. The conformations of BCGCSP in solutions were investigated by means of NMR, Raman, and CD spectroscopy. The 1H-NMR data in dimethyl-d6 sulfoxide (Me2SO-d6) demonstrated that the two cyclic skeletons of BCGCSP take the same conformations as that of an authentic cyclic tetrapeptide, cyclo[Gly–L-Cys(Bzl(OMe))–Sar–L-Pro] (CGCSP). The 1H-NMR spectrum of CGCSP contains three sets of resonances, corresponding to three different molecular conformations. From the Raman lines of BCGCSP at 529 cm−1 and 683 cm−1 in Me2SO-d6, it is deduced that the two HCα-CβS dihedral angles are 180°(trans), while one of the SS–CβCα dihedral angles is 20–30° and the other is either near 90° or near 180°. In addition, the values of two Raman lines predict that the CβS–SCβ dihedral angle is in the range of near 90°. Such a conformation around the CβS–SCβ bond is also reasonable in the light of the presence of a CD transition (CS–SC) at λ>250 nm in water. By combining the above data, the CPK molecular model of BCGCSP was constructed. An inspection of the model reveals that this bis(cyclic tetrapeptide) is likely to adopt a “castanet-type” structure in Me2SO-d6. At the same time the individual cyclic skeleton is considered to take three different ring conformations in equilibrium.
  • Toshimi Shimizu, Yoshio Tanaka, Keishiro Tsuda
    1982 Volume 55 Issue 12 Pages 3817-3823
    Published: 1982
    Released: June 27, 2006
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    The conformations of the cyclic tetrapeptide, cyclo[Gly–L-Cys(Bzl(OMe))–Sar–L-Pro] (CGCSP), in solution, were studied by means of 1H-, 13C-nuclear magnetic resonance (NMR), and circular dichroism (CD). The CGCSP equilibrates among three conformers, M, m, and n, in acetonitrile, providing three sets of resonances for each proton in the 1H-NMR spectrum. An inspection of a CPK model indicated that the three structures were sterically allowed to occur by the cis-trans isomerism around the Cys-Sar and Sar-Pro peptide bond. The temperature dependence of the amide proton resonances in 1H-NMR suggested that one γ-turn (1←3 hydrogen bond from the Cys to the Pro) is present in the two conformers, M and m. Thus, the three conformations in acetonitrile were deduced from all of the spectral data. This cyclic tetrapeptide is capable of binding a monovalent cation, Li+, and divalent cations, Mg2+, Ca2+, and Ba2+. Its CD titration curves demonstrated that at least three types of complexes with Ca2+ and Ba2+ were formed. In contrast, Li+ and Mg2+ were shown to form the 1 : 1 complex with this pep tide. The NMR data suggest that the conformational change of the cyclic backbone takes place by changing the geometry of the peptide bonds around the Cys–Sar–Pro sequence on the addition of a metal cation.
  • Hiroyoshi Kamogawa, Shuji Yamamoto, Masato Nanasawa
    1982 Volume 55 Issue 12 Pages 3824-3827
    Published: 1982
    Released: June 27, 2006
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    Vinyl monomers containing saccharin or cyclamate residues were synthesized. 6-Acrylamido-, 6-methacrylamido-, 6-(4-styrenesulfonamido)-, and 6-(vinylbenzylamino)saccharins were synthesized from 6-aminosaccharin. N-[2-(4-Styrenesulfonamido)cyclohexyl] and N-[2-(vinylbenzylamino)cyclohexyl]sulfamic acids were synthesized starting with 1,2-cyclohexanediamine via sodium N-(2-aminocyclohexyl)sulfamate. All monomers thus synthesized were found to polymerize or copolymerize with N-vinyl-2-pyrrolidone to afford vinyl polymers with pendant saccharin and cyclamate units.
  • Noriko Hasaka, Masayoshi Okigawa, Isao Kouno, Nobusuke Kawano
    1982 Volume 55 Issue 12 Pages 3828-3830
    Published: 1982
    Released: June 27, 2006
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    Optically active (−)- and (+)-2,2′,6,6′-tetrafluorobiphenyl-3,3′-dicarboxylic acids were obtained through brucine salts. The half-life times for racemization of their dimethyl esters were estimated at various temperatures and the activation energy was calculated to be 25.6 kcal/mol.
  • Takashi Matsumoto, Koji Iyo, Shigekazu Miuchi
    1982 Volume 55 Issue 12 Pages 3831-3835
    Published: 1982
    Released: June 27, 2006
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    Catalytic hydrogenation of 19-norabieta-4(18),8,11,13-tetraen-3α-ol over Raney Ni and subsequent dehydration afforded 18-norabieta-2,8,11,13-tetraene, which was converted into 3α-bromo-18-norabieta-8,11,13-trien-2-one (8) via a bromohydrin. Acetalization of 8 with 1,2-ethanediol in the presence of p-toluenesulfonic acid afforded a mixture of 3α-bromo-2,2-ethylenedioxy-18-norabieta-8,11,13-triene (10) and its 3β-bromo isomer (11) in a ratio of ca. 2 : 3. Oxidation of 10 and 11 with chromium trioxide in acetic acid gave the corresponding ketones 12 and 13. The ketone 13 was then converted into a diosphenol derivative, 3β-bromo-2,2-ethylenedioxy-6-hydroxy-18-norabieta-5,8,11,13-tetraen-7-one (14), by treatment with oxygen in the presence of potassium t-butoxide. Hydrolysis of 14 with dilute hydrochloric acid followed by dehydrobromination afforded the desired analog, 6-hydroxy-19-norabieta-3,5,8,11,13-pentaene-2,7-dione. A related A/B ring oxygenated compound, 19-norabieta-3,5,8,11,13-pentaene-2,7-dione was also synthesized from 12 and 13 via the corresponding 6α-bromo derivatives.
  • Takashi Matsumoto, Sachihiko Imai, Shuhei Yuki
    1982 Volume 55 Issue 12 Pages 3836-3839
    Published: 1982
    Released: June 27, 2006
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    Oxidation of 11-acetoxyabieta-8,11,13-triene, derived from methyl 11-methoxyabieta-8,11,13-trien-18-oate, with chromium trioxide afforded 11,15-diacetoxyabieta-8,11,13-trien-7-one and 11-acetoxy-13-acetylpodocarpa-8,11,13-trien-7-one (11) in a ratio of ca. 2 : 1. The acetyl compound 11 was converted into a quinone, 13-(hydroxymethyl)podocarpa-8,12-diene-11,14-dione (18), by a series of reactions : iodoform reaction, esterification, acetylation, sodium borohydride reduction, dehydration, catalytic hydrogenation, lithium aluminium hydride reduction, and oxidation with Fremy’s salt. Reductive acetylation of 18 produced 11,14-diacetoxy-13-(acetoxymethyl)-podocarpa-8,11,13-triene (2). The 1H NMR spectrum of 2 was different from that of 15-acetoxypremnol diacetate which was prepared from natural premnolal. Based on this fact a corrected structure of premnolal is proposed.
  • Kin-ichi Tadano, Tohru Tsuchiya, Tetsuo Suami, Kenneth L. Rinehart
    1982 Volume 55 Issue 12 Pages 3840-3846
    Published: 1982
    Released: June 27, 2006
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    Three potential biosynthetic intermediates for aminocyclitol antibiotics, neosamine C-CDP, -UDP, and -ADP, have been synthesized from D-glucosamine by chemical means. 2,6-Diamino-2,6-dideoxy-α-D-glucopyranosyl phosphate, derived from the corresponding glycosyl bromide, was condensed with three nucleosides (CMP, UMP and AMP) by a known procedure. The configurations of the neosamine C nucleoside diphosphates have been confirmed by 13C NMR spectra.
  • Takamitsu Yoshioka, Toshifumi Hirata, Tadashi Aoki, Takayuki Suga
    1982 Volume 55 Issue 12 Pages 3847-3851
    Published: 1982
    Released: June 27, 2006
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    On the basis of the 1H NMR spectroscopy and the X-ray crystallography, the configuration at C-4 of herqueinone was determined to be S and the configurations at C-3 and C-4 of dihydroherqueinone monomethyl ether were elucidated to be R and S, respectively, with relation to the previously established R-configuration at the 2′-position of herqueinone.
  • Shigeru Futamura, Kazuhiro Yamazaki, Hiroyuki Ohta, Yoshio Kamiya
    1982 Volume 55 Issue 12 Pages 3852-3855
    Published: 1982
    Released: June 27, 2006
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    9,10-Dicyanoanthracene (DCA)-sensitized photooxidation reactions of hindered phenols and catechols (1) proceed via the initial electron transfer from 1 to 1DCA*. 4-Hydroperoxy-2,5-cyclohexadien-1-ones and 4-hydroxy-2,5-cyclohexadien-1-ones are obtained from 2,4,6-trialkyl-substituted phenols, and an o-benzoquinone and furanone derivatives are afforded from 3,5-di-t-butylcatechol.
  • Hideo Kise, Kazutoshi Iwamoto, Manabu Sen\={o}
    1982 Volume 55 Issue 12 Pages 3856-3860
    Published: 1982
    Released: June 27, 2006
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    The infrared spectra of the solutions of dodecylammonium propionate (DAP), hexadecyltrimethylammonium bromide (HTAB), and sodium bis(2-ethylhexyl) 2-sulfonatosuccinate (SBSS) in organic solvents were recorded in Fourier transform mode. Difference concentration spectra of DAP in dichloromethane exhibited the change in the stretching bands of the carboxylate ions, which was attributed to the formation of micellar aggregates. Difference hydration spectra were also obtained for water-containing DAP–CH2Cl2, HTAB–CH2Cl2, and SBSS–benzene systems, and the spectra in the region of 3000–3700 cm−1 and 1600–1650 cm−1 revealed the existence of free water dispersed in the organic phase and water bound to the micelles. The diffreence spectra also revealed the change in the bands of DAP and SBSS due to hydration of the ionic head groups. The absorption frequency of the O–H stretching bands was discussed in terms of the water-surfactant-interaction.
  • Toshio Itahara, Hiroshi Ouya, Kiyotake Kozono
    1982 Volume 55 Issue 12 Pages 3861-3864
    Published: 1982
    Released: June 27, 2006
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    The autoxidation of 3-alkyl-2-methylindoles in carboxylic acids, such as propionic acid and acetic acid, at the reflux temperature resulted in the selective oxidation of the 2-methyl group and the formation of 3-alkyl-2-formylindoles. The formation of the 2-formylindoles was dependent on the nature of the solvent used. The treatment of 3-benzoyl-1,2-dimethylindole with silver acetate gave 2-acetoxymethyl-3-benzoyl-1-methylindole and 3-benzoyl-2-formyl-1-methylindole. The mechanistic implications for the autoxidation and the oxidation with silver acetate are presented.
  • Masaru Tada, Hirohide Hamazaki, Hideki Hirano
    1982 Volume 55 Issue 12 Pages 3865-3869
    Published: 1982
    Released: June 27, 2006
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    The irradiation of 4′-(5,6-dicyano-2-pyrazinyl)benzo-15-crown-5 and 5,6-dicyano-2-(3,4-dimethoxyphenyl)pyrazine in the presence of a tertiary or secondary amine caused reductive decyanation to give 5-decyano derivatives, which in turn gave bis(decyano) derivatives on further irradiation. Free-energy changes upon single-electron transter from the amine to the excited state of dicyanopyrazine derivatives are exothermic for triethylamine and diethylamine, but endothermic for butylamine. The single-electron transfer was evidenced by the effect of the sodium ion on the quantum yields of the reaction products and the fluorescence quenching.
  • Yasuo Kitajima, Michinori Waki, Nobuo Izumiya
    1982 Volume 55 Issue 12 Pages 3870-3872
    Published: 1982
    Released: June 27, 2006
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    Four isomers of histopine, N2-(1-carboxyethyl)histidine, were prepared to provide their physicochemical properties. A diastereomeric mixture, (RS),(S)-histopine (N2-[(RS)-1-carboxyethyl]-(S)-histidine), was synthesized from 2-oxopropionic acid and (S)-histidine by reduction with sodium cyanoborohydride. The mixture was separated into its components, (S),(S)-histopine and (R),(S)-histopine, by an ion-exchange column chromatography. In a similar manner (R),(R)-histopine and (S),(R)-histopine were prepared. Configurations of the four isomers obtained were assumed from their ORD data by comparison with those of the isomers of octopine (N2-(1-carboxyethyl)arginine) with a definite configuration.
  • Yoshio Kamiya, Tadashi Yao, Shinichi Nagae
    1982 Volume 55 Issue 12 Pages 3873-3877
    Published: 1982
    Released: June 27, 2006
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    In order to study the effect of solvent on the liquefaction of coal as a function of coal rank, the liquefaction of five kinds of coals from carbon content of 66% to 83% were carried out in the presence of various aromatic solvents. It was found that three ring aromatic hydrocarbons were more powerful solvent for the liquefaction. Hydrogen donor solvents such as tetralin and hydrophenanthrenes were most effective of all solvents tested independent of coal rank. A mixture of hydrogen donor and polar compounds such as phenol and quinoline was confirmed to be effective to bituminous coal but not so effective to brown coal. It should be stressed that hydrogen donating property of solvent is most important for low rank coals. The chemical analyses of products have shown that the properties of solvent refined coal are a little affected by the quality of solvent.
  • Tateaki Wakamiya, Kuniaki Shimbo, Tetsuo Shiba, Kiichiro Nakajima, Mas ...
    1982 Volume 55 Issue 12 Pages 3878-3881
    Published: 1982
    Released: June 27, 2006
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    threo-3-Methyl-D-cysteine as a moiety of β-methyllanthionine in the peptide antibiotic nisin was synthesized stereospecifically. The reaction of (2R,3R)-3-methyl-2-aziridinecarboxylic acid derivative prepared from D-threonine with thiobenzoic acid gave the β-mercapto α-amino acid derivative of the same configuration as the starting material. A stereochemistry of the product was retained as a result of double inversion mechanism through the reactions. Thus, we could prepare threo-3-methyl-D-cysteine, i.e., (2S,3S)-2-amino-3-mercaptobutanoic acid which is required for the synthetic study of nisin.
  • Hiroshi Tsukube
    1982 Volume 55 Issue 12 Pages 3882-3886
    Published: 1982
    Released: June 27, 2006
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    A variety of crown ethers and their analogs which contain powerful hydrogen bonding sites such as pyridine and quinoline moieties were examined as new synthetic carrier. Among the examined carriers, acyclic crown ethers and their polymers having pyridine groups were found to be selective and efficient carriers for some organic ammonium cations of great biological significances. Their transport properties were largely different from those of usual crown ether compounds, and essentially dependent on the combined characteristics of polyether sequence, hydrogen bonding site, co-transported anion, and others.
  • Hideki Masuda, Tooru Taga, Kenji Osaki, Hiroshi Sugimoto, Masayasu Mor ...
    1982 Volume 55 Issue 12 Pages 3887-3890
    Published: 1982
    Released: June 27, 2006
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    The crystal structure of μ-oxo-bis[(octaethylporphinato)ruthenium(IV) chloride] benzene solvate, [Ru(IV)(oep)Cl]2O–C6H6, was determined by the X-ray method. The complex crystallizes in the tetragonal space group P4/nnc, a=13.912(2) Å, c=17.821(4) Å, and Z=2. The structure was solved by the heavy-atom method and refined to R=0.084 for 958 reflections. The [Ru(IV) (oep)Cl]2O complex has the crystallographic D4-422 symmetry and contains the binuclear (Cl)N4Ru–O–RuN4(Cl) coordination group with the Ru–O(μ) distance of 1.793(2) Å, the Ru–Cl distance of 2.320(6) Å, and the Ru–N distance of 2.038(9) Å. The Ru–O–Ru bond is explicitly linear, and the two porphinato cores rotate around the Ru–O–Ru bond by 21.0° from the eclipsed form. The porphinato core is planar within 0.04 Å, and the Ru atom is displaced only by 0.07 Å out of the plane defined by the four porphinato nitrogen atoms toward the bridging O atom. These results are compared with those of the previously reported [Ru(IV)(oep)(OH)2]O–CH3OH crystal.
  • Hideki Masuda, Tooru Taga, Kenji Osaki, Hiroshi Sugimoto, Zen-ichi Yos ...
    1982 Volume 55 Issue 12 Pages 3891-3895
    Published: 1982
    Released: June 27, 2006
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    The crystal structure of (octaethylporphinato)bis(tetrahydrofuran)iron(III) perchlorate was determined by the X-ray method. The complex crystallizes in the monoclinic space group C2/m, a=13.916(3) Å, b=16.509(3) Å, c=10.659(5) Å, β=118.18(1)°, and Z=2. The structure was solved by the direct method and refined by the full-matrix least-squares method. The final R value was 0.079 for 597 reflections. The complex has a crystallo-graphically imposed twofold axis and a mirror of symmetry. The porphinato core is planar within 0.06 Å. The iron(III) ion lies at the center of the octahedron formed by the four porphinato nitrogen atoms and the two tetrahydrofuran oxygen atoms. The axial Fe–O distance, 2.187(11) Å, is considerably longer than the reported distances for high-spin porphinatoiron(III) complexes, while the equatorial Fe–N distance, 1.978(12) Å, is comparable to those for low-spin and intermediate-spin porphinatoiron(III) complexes. The Fe–O and Fe–N bond distances are well explained in terms of an intermediate-spin state of the iron(III) ion.
  • Atsushi Terahara, Hiroaki Ohya-Nishiguchi, Noboru Hirota, Yoshiteru Sa ...
    1982 Volume 55 Issue 12 Pages 3896-3898
    Published: 1982
    Released: June 27, 2006
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    The cation radicals of three [2.2]pyrenophanes in which two pyrene moieties are twisted each other by 0°, 35°, and 60° were investigated by ESR, ENDOR, and cyclic voltammetry. Considerable variations of the spin density distribution and the stabilization energy with the twisting angle have been observed. The obtained results are discussed in terms of modified Hückel-McLachlan type calculation.
  • Hiroyasu Nomura, Hayao Shimizu, Yasuharu Tanaka, Shinobu Koda, Toshio ...
    1982 Volume 55 Issue 12 Pages 3899-3903
    Published: 1982
    Released: June 27, 2006
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    An apparatus for the accurate measurement of Brillouin scattering of liquids and solutions was constructed using a multi-pass Fabry-Perot interferometer. The Brillouin scattering spectra of chloroform–eicosane mixtures were obtained at various concentrations. The sound velocity dispersion curves of this system could be expressed by a single relaxation equation. With increasing concentration of eicosane, the relaxation frequency shifted to the higher frequency side, but the relaxation strength was independent of concentration. It is concluded that this relaxation was due to the vibrational-translational energy transfers of chloroform molecules due to the collisions between chloroform and eicosane molecules.
  • Kazuaki Harata, Kaneto Uekama, Masaki Otagiri, Fumitoshi Hirayama
    1982 Volume 55 Issue 12 Pages 3904-3910
    Published: 1982
    Released: June 27, 2006
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    The crystal structure of the hexakis(2,3,6-tri-O-methyl)-α-cyclodextrin (abbreviated to methyl-α-CDx) complex with p-nitrophenol, C54H96O30·C6H5NO2·H2O, was investigated by the X-ray method. The crystal is monoclinic, the space group being P21 with Z=2; the cell dimensions are a=11.307(1), b=14.578(1), c=22.118(2) Å, and β=93.62(1)°. The structure was determined by means of the Patterson map and the trial-and-error method combined with the rigid-body least-squares technique, and refined by the block-diagonal least-squares method to the final R-value of 0.048 for 4976 reflections (sinθ⁄λ<0.54). The methyl-α-CDx molecule has the shape of a truncated hexagonal cone, into which the p-nitrophenol molecule is inserted. The phenolic hydroxyl group is located at the center of the methyl-α-CDx cavity, while the nitro group protrudes outside from the base-side of the host cone and is in contact with the adjacent methyl-α-CDx molecule. The water molecule, which is also located within the cavity, links the methyl-α-CDx and p-nitrophenol molecules by hydrogen bonds. Methyl-α-CDx molecules are stacked along the crystallographic a axis in a heat-to-tail mode to form a channel-type structure.
  • Masaharu Nomura, Kiyotaka Asakura, Ukyo Kaminaga, Tadashi Matsushita, ...
    1982 Volume 55 Issue 12 Pages 3911-3914
    Published: 1982
    Released: June 27, 2006
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    A dispersive-type in-laboratory EXAFS spectrometer was constructed by combining a transmission-type dispersing crystal and a position-sensitive proportional counter. FeK absorption spectra were measured by use of this apparatus on FeCl3·6H2O, Fe(ClO4)3·6H2O and anhydrous FeCl3. Discussion is given on the results obtained from the analyses of observed EXAFS data concerning the structure around Fe ions in these compounds. AsI3-like structure is proposed for anhydrous FeCl3.
  • Tsunetoshi Kobayashi, Tanekazu Kubota, Kiyoshi Ezumi, Chikatoshi Utsun ...
    1982 Volume 55 Issue 12 Pages 3915-3919
    Published: 1982
    Released: June 27, 2006
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    Photoelectron spectra of isoxazole, 5-methylisoxazole, and 3,5-dimethylisoxazole were studied by the technique of photoelectron angular distribution measurements combined with a first order perturbation theoretic approach. Photoelectron spectra of oxazole, 4-methyloxazole, furan, and 2-methylfuran, which are closely related to isoxazole, were also discussed at the same time for the sake of comparison. The first three bands of the isoxazoles were assigned to the π, π, and n bands from the top, respectively, while those of the oxazoles were identified as the π, n, and π bands from the top.
  • Masaaki Ito, Kazuo Abe, Teruji Sasaki, Norimitsu Wakabayashi, Kenzo Mi ...
    1982 Volume 55 Issue 12 Pages 3920-3922
    Published: 1982
    Released: June 27, 2006
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    The chemical desalting technique was applied to the concentrated Steffen fluid using concd sulfuric acid and methanol. The chemical components of the isolated salt were studied by scanning electron microscopy, infrared spectroscopy, X-ray diffraction, and fluorescence analyses. The main constituent of the salt was determined to be K3Na(SO4)2 and then synthesized.
  • Kenichi Nakashima, Motohiko Koyanagi
    1982 Volume 55 Issue 12 Pages 3923-3924
    Published: 1982
    Released: June 27, 2006
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    The near ultraviolet absorption spectra of benzaldehyde have been studied in various fluid solutions at room temperature. The intensity enhancements observed are explainable in terms of perturbation of dispersion forces between solute and solvent molecules.
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