Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Volume 56 , Issue 3
Showing 1-50 articles out of 80 articles from the selected issue
  • Isao Tanaka, Naoki Jin-no, Takanori Kushida, Noriyoshi Tsutsui, Tamaic ...
    1983 Volume 56 Issue 3 Pages 657-661
    Published: 1983
    Released: June 27, 2006
    JOURNALS FREE ACCESS
    The crystal structures of (1,5-cyclooctadiene)di-μ-methoxo-dirhodium(I) and tetrakis(η3-allyl)di-μ-hydroxodirhodium(III) were determined by the X-ray method. The former belongs to the triclinic space group P\bar1 with cell dimensions, a=7.347(4), b=6.471(3), c=9.554(6) Å, α=87.06(4), β=82.50(5) and γ=77.98(4)°. The space group of the latter is also P\bar1 but two crystallographically independent molecules exist in a cell with dimensions, a=11.704(7), b=9.793(6), c=7.948(5) Å, α=113.49(5), β=54.59(5), and γ=110.99(5)°. Both structures were determined by the heavy atom method and refined by the block-diagonal least-squares method. The final R values were 0.054 for the former and 0.075 for the latter. The coordination of the rhodium atom in the former compound is square planar, the cyclooctadiene ligand being regarded as a bidentate donor. The latter coordination is, in a formal sense, octahedral.
  • Jun-ichi Hamada, Shigeru Tsunashima, Shin Sato
    1983 Volume 56 Issue 3 Pages 662-666
    Published: 1983
    Released: June 27, 2006
    JOURNALS FREE ACCESS
    The reactions of NH radicals with C4 olefins, trans- and cis-2-butenes, 1-butene, and isobutene, were investigated by the photolysis of hydrogen azide in the liquid olefin at 0 °C and at the temperature of Dry Ice–methanol. Except for nitrogen and ammonia, amines and aziridines were found to be formed in good yield. 2-Butene-1-amine and trans-2,3-dimethylaziridine from trans-2-butene, 2-butene-1-amine and cis-2,3-dimethylaziridine from cis-2-butene, 3-butene-1- and 2-amines and 2-ethylaziridine from 1-butene, and 2-methyl-2-propene-1-amine and 2,2-dimethylaziridine from isobutene. These product formations were successfully explained by the insertion into the C–H bond and the addition to the double bond of olefin by the singlet NH radicals. In the case of 2-butene, no isomerized aziridine formation was observed. This result suggested that the triplet NH radicals rarely add to the double bond of olefin.
  • Toshiya Endo, Ichio Shimada, Fuyuhiko Inagaki, Tatsuo Miyazawa
    1983 Volume 56 Issue 3 Pages 667-670
    Published: 1983
    Released: June 27, 2006
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    The base-catalyzed hydrogen→deuterium exchange rates of the imidazole C-2 protons were measured for the imidazole-bearing molecules with amino groups (N2H2·Im) in 2H2O at various pH. From the pH dependences of the pseudo-first-order rate constants, the second-order rate constants were obtained for the N2H3+·Im2H+ species and for the equilibrium mixtures of the N2H2·Im2H+ and N2H3+·Im species. For both the N2H3+·Im2H+ and N2H2·Im2H+ species, the second-order rate constants and microscopic dissociation constants of the imidazolium rings were found to satisfy the Brφnsted relation, with concomitant estimation of the abundance ratio of the N2H2·Im2H+ and N2H3+·Im species. This abundance ratio was compared with that estimated from the pH dependence of proton chemical shifts.
  • Hitoshi Fujimoto, Masashi Tanaka, Jiro Tanaka
    1983 Volume 56 Issue 3 Pages 671-675
    Published: 1983
    Released: June 27, 2006
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    Infrared and visible absorption spectra of (CH)x, (CD)x, and the copolymers [(C2H2)1−y(C2D2)y]x doped with Br2 or I2 were measured for various values of y between 0 and 1. By the doping, the π→π* band located in the 19000 cm−1 region disappeared while several new bands were observed at 800–900-, 1000–1400-, and 5000-cm−1 regions. The absorption band shapes and the locations of the 5000- and 19000-cm−1 bands did not depend appreciably upon the value of y. The charged soliton induced vibrational bands were found at 870-and 1370-cm−1 in (CH)x and 1230-, 1100-, and 780-cm−1 in (CD)x. In addition, another new bands were found around 570–660 cm−1 region by decreasing the temperature of the doped film to 160 K. These new bands were not shifted by the isotopic substitution. A plausible mechanism for the appearance of this band is suggested as an oscillation of trapped charged soliton around the negatively charged dopant. For the heavily doped (CH)x film, the gapless transition was observed and the optical conductivity was estimated by the Drude formula and was compared with the value obtained by a direct conductivity measurement.
  • Kazuro Kawamura
    1983 Volume 56 Issue 3 Pages 676-679
    Published: 1983
    Released: June 27, 2006
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    Radicals formed spontaneously during the cure reaction of epoxy resins with 2,4,6-trinitrophenol (TNP) or 2,4,6-trinitroresorcinol (TNR) have been investigated using electron spin resonance (ESR) technique. The ESR spectrum of the radicals stabilized in the epoxy resins cured with TNP was a triplet and the other spectrum of the radicals in the epoxy resins cured with TNR was a triplet with high anisotropy. The triplet splittings and g-values were attributed to radicals of the type (Remark: Graphics omitted.). The asymmetric line shapes of the triplet splittings caused by the 14N coupling constant are induced by the slow motion of the radicals in the polymer. The presence of radicals of this type suggests the transfer of an oxygen of a nitro group of TNP or TNR during the cure reaction.
  • Yosuke Yoshimura, Jiro Osugi, Masaru Nakahara
    1983 Volume 56 Issue 3 Pages 680-683
    Published: 1983
    Released: June 27, 2006
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    A high pressure kinetic study was made of the 1,3-dipolar cycloaddition reaction of Ph2CN2 with dimethyl maleate (DMM), dimethyl fumarate (DMF), methyl acrylate (MA), maleonitrile (MN), fumaronitrile (FN), and acrylonitrile (AN) in toluene at 25 °C. The activation volumes (ΔV\ eweq) at 1 bar obtained for DMM, DMF, MA, MN, FN, and AN are −23.4±0.5, −22.3±0.2, −19.8±0.4, −21.5±0.6, −21.0±1.1, and −23.9±0.5 cm3 mol−1, respectively. The reaction volume (ΔV) for the reaction between Ph2CN2 and DMM was determined dilatometrically by taking advantage of supersaturation of the cycloadduct in solution; ΔV=−24.5±0.5 cm3 mol−1 and ΔV\ eweq⁄ΔV=0.955. The present volumetric information coupled with a kinetic analysis shows that Firestone’s biradical mechanism is not the case; the concerted mechanism is supported. The experimental result is compared with that of a recent ab initio molecular orbital calculation with respect to the activation and reaction volumes.
  • Kazuo Kojima, Minoru Saida, Masami Donoue, Jiro Matsuda
    1983 Volume 56 Issue 3 Pages 684-688
    Published: 1983
    Released: June 27, 2006
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    The visible absorption spectra of CoX2 (X=Cl, Br) in pyridine solutions have been measured in the ranges 1 bar—3 kbar at room temperature, and ≈4—≈70 °C at 1 atm. The equilibrium, [CoX2(py)2](tetrahedral)+2py\ ightleftharpoons[CoX2(py)4](octahedral), is found to be followed over these pressure and temperature ranges. High pressure favors the octahedral species, with the volume changes, −41 cm3/mol for the chloride and ≈−30 cm3/mol for the bromide at 1 atm. The pressure dependence of the volume change is less for the bromide than for the chloride. High temperature, however, favors the tetrahedral species, with the heats of reaction, 57.3 and 60.7 kJ/mol for the chloride and the bromide, respectively. Some discussions on both the effects are also presented.
  • Kenzo Kitayama, Daizo Zoshima, Takashi Katsura
    1983 Volume 56 Issue 3 Pages 689-694
    Published: 1983
    Released: June 27, 2006
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    The phase equilibria in the La2O3–V2O3–V2O5 system were established at 1200 °C by changing oxygen partial pressures from −0.68 (air) to −13.00 in terms of logPO2. In this system, 0.81La2O3·0.19V2O5(La1.62V0.38O3.38), 3La2O3·V2O5(La3VO7), 0.71La2O3·0.29V2O5(La1.42V0.58O3.58), LaVO4, LaVO3, VnO2n−1 (n=2–7), and VO2 were stable. LaVO3, LaVO4, La1.62V0.38O3.38, La3VO7, and La1.42V0.58O3.58 have nonstoichiometric compositions. On the basis of the phase equilibria, the Gibbs energies of the reactions:
    31⁄50La2O3+19⁄50LaVO3+19⁄100O2=La1.62V0.38O3.38
    50⁄31La1.62V0.38O3.38+12⁄31LaVO3+6⁄31O2=La3VO7
    21⁄50La3VO7+4⁄25 LaVO3+2⁄25O2=La1.42V0.58O3.58
    LaVO3+1⁄2O2=LaVO4
    were determined to be −64.0, −55.8, −21.6, and −131.5 kJ respectively.
  • Kenzo Kitayama, Chikaaki Mizokuchi, Takashi Katsura
    1983 Volume 56 Issue 3 Pages 695-699
    Published: 1983
    Released: June 27, 2006
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    Phase equilibria in the Nd2O3–V2O3–V2O5 system were established at 1200 °C by changing the oxygen partial pressures from −0.68 (air) to −12.50 in terms of logPO2. In this system, VnO2n−1 (n=2–7), VO2, Nd2O3, NdVO3, NdVO4, 0.81Nd2O3·0.19V2O5 (Nd1.62V0.38O3.38, A), and 3Nd2O3·V2O5 (Nd3VO7, B) were stable under the present experimental conditions. Compounds with Nd2O3/V2O5 mole ratios of 6/1 and 2/1 were not found under the present experimental conditions. Compounds A, Nd3VO7, NdVO3, and NdVO4 have nonstoichiometric compositions. The pattern of the phase diagram is different from those of other Ln2O3–V2O3–V2O5 systems that have previously been established by us. On the basis of the phase diagram, the Gibbs energies of the reactions:
    (1) 31⁄50Nd2O3+19⁄50NdVO3+19⁄100O2=Nd1.62V0.38O3.38
    (2) 50⁄31Nd1.62V0.38O3.38+12⁄31NdVO3+6⁄31O2=Nd3VO7
    (3) NdVO3+1⁄2O2=NdVO4
    were determined to be −61.4, −47.4, and −128.9 kJ respectively. In the Nd2O3–V2O3 system, only NdVO3 is stable under the present experimental conditions.
  • Tatsuya Sekine, Takashi Saitou, Hiroto Iga
    1983 Volume 56 Issue 3 Pages 700-704
    Published: 1983
    Released: June 27, 2006
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    Distribution of six β-diketones between hexane, benzene, carbon tetrachloride, or chloroform and 0.1 mol dm−3 aqueous perchlorate solutions has been measured in the presence of trioctylphosphine oxide (TOPO). The distribution ratio was, in many cases, enhanced by TOPO; this was explained in terms of association of the β-diketones and TOPO. The association constants were greater when the β-diketone was stronger as an acid and also in the following order of the diluent: CHCl3<CCl4<C6H6<C6H14. It was concluded that, even though the effect was not very large, still correction for the decrease in the concentrations of both the β-diketone and TOPO is necessary for an accurate estimation of the equilibrium involved in solvent extraction of metal ions containing these two reagents, as in the synergistic solvent extraction of metal ions.
  • Yasushi Inoue, Yoshimune Yamada
    1983 Volume 56 Issue 3 Pages 705-708
    Published: 1983
    Released: June 27, 2006
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    The sodium isotopic exchange rate between the large crystals of disodium zirconium(IV) bis(orthophosphate) trihydrate and aqueous solutions was determined radiochemically. The exchange proceeded quickly up to 5% of the total, followed by a slow process. The first step was attributed to the instantaneous attainment of the equilibrium between the imperfect surface layers of the crystals and the solution, and the second step was found to be controlled by the diffusion of sodium ions along the direction perpendicular to the layers consisting of zirconium atoms. The diffusion constant, D, was calculated with the equation obtained by Fick’s diffusion law under the conditions of slab geometry and infinite solution volume. From the dependence of D on temperature, the activation energy for the diffusion was evaluated to be 101 kJ mol−1.
  • Shunichi Fukuzumi, Nobuaki Nishizawa, Toshio Tanaka
    1983 Volume 56 Issue 3 Pages 709-714
    Published: 1983
    Released: June 27, 2006
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    A dimeric RhI complex, [Rh2(dicp)4]2+ (dicp=1,3-diisocyanopropane) was found to undergo a photoinduced oxidative addition with butyl iodide and isopropyl iodide in MeCN by 553 nm irradiation in high quantum yields, Φ=25.2 and 22.6, respectively. Electron acceptors (p-dinitrobenzene, p-benzoquinone, and chloranil) and radical scavengers (oxygen and isopentyl nitrite) act as inhibitors for the photoinduced oxidative addition, providing unambiguous evidence for a chain character of this reaction. The fluorescence quenching of [Rh2(dicp)4]2+ by the electron acceptors as well as butyl iodide has also been examined. Based on the kinetics of the photochemical reactions in the absence or the presence of electron acceptors and radical scavengers, an electron transfer chain mechanism has been proposed. The formation of butyl radicals in the photoinitiation step was confirmed by the trap with oxygen to yield equimolar amounts of 1-butanol and butyraldehyde. The nature of the excited state of [Rh2(dicp)4]2+*(1A2u or 3A2u) involved in the photoinitiation step has also been discussed.
  • Minoru Suzuki, Kuniko Koizumi, Hajime Kikuchi, Teruaki Suzuki, Etsuro ...
    1983 Volume 56 Issue 3 Pages 715-718
    Published: 1983
    Released: June 27, 2006
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    A new halogenated nonterpenoid C15-compound, epilaurallene, has been isolated as a major constituent from the title alga along with several known compounds, and its structure was determined by the spectral and chemical methods. Epilaurallene is an epimer at C-4 of laurallene and was shown to possess S-configuration at C-4.
  • Toshiro Chiba, Mitsuhiro Okimoto, Hiroshi Nagai, Yoshiyuki Takata
    1983 Volume 56 Issue 3 Pages 719-723
    Published: 1983
    Released: June 27, 2006
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    The Raney nickel catalyst was employed as a catalytic electrode in the electrohydrogenation of various unsaturated compounds, including ketones, aromatic aldehydes, Schiff’s bases, oximes, nitriles, aromatic nitro compounds, olefins, and acetylenes. The hydrogen generated electrochemically was adsorbed and activated at the surface of the catalyst; it effectively hydrogenated these compounds, affording products which are very similar to those obtained in a normal catalytic hydrogenation with Raney nickel.
  • Nobuo Ishikawa, Tsutomu Yokozawa
    1983 Volume 56 Issue 3 Pages 724-726
    Published: 1983
    Released: June 27, 2006
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    The preparative method for dimethyl (trifluoromethyl)malonate (4) from the adduct of perfluoro-2-methylpropene with methanol was improved, and several reactions of this base-sensitive substance were investigated. Alkylation of 4 was achieved by using CsF as a condensing agent, and the Michael addition on vinyl ketones proceeded in triethylamine–pyridine medium.
  • Takayuki Matsushita, Toshiyuki Shono
    1983 Volume 56 Issue 3 Pages 727-733
    Published: 1983
    Released: June 27, 2006
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    The copper(II) complex of salicylideneamine (salamH) reacts with molecular oxygen in pyridine to give the 2-cyanophenolato complex, [Cu(2-CNphO)2(py)2], in good yield, where 2-CNphOH and py denote 2-cyanophenol and pyridine, respectively. This complex was characterized by the infrared and electronic spectra and by its magnetic susceptibilities, and was compared with the authentic complex, [Cu(2-CNphO)2(py)2]. The mechanism for the oxidation of the coordinated imino groups is discussed.
  • Yoshitsugu Hasegawa, Seiichi Kizaki, Hiroshi Amekura
    1983 Volume 56 Issue 3 Pages 734-737
    Published: 1983
    Released: June 27, 2006
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    The ion-exchange properties of α-zirconium phosphate have been investigated for the H+–[Co(NH3)6]3+ system. The ion-exchange process was examined by means of the variation in the pH values of the supernatant. α-Zirconium phosphate loaded with hexaamminecobalt(III) was also characterized by chemical analysis, X-ray diffractometry, infrared spectroscopy, and thermal analysis. In spite of the steric hindrance in the crystal structure of α-zirconium phosphate, the ion exchange proceeded gradually. About 30% of the hydrogen ions in α-zirconium phosphate were replaced by hexaamminecobalt(III). The interlayer distance of the exchanger expanded from 0.76 to 1.12 nm.
  • Yoshiyuki Hirashima, Koji Kanetsuki, Ikuo Yonezu, Kiyohito Kamakura, J ...
    1983 Volume 56 Issue 3 Pages 738-743
    Published: 1983
    Released: June 27, 2006
    JOURNALS FREE ACCESS
    Lanthanoid nitrates (Ln(NO3)3) formed solid complexes with several polyethylene glycols and glymes. The compositions of the complexes were 1:1 (Ln:ligand) for triethylene glycol(EO3), tetraethylene glycol(EO4), pentaethylene glycol(EO5), and tetraglyme, 1:2 (Ln:ligand) for diethylene glycol, 2:1 for heptaethylene glycol, and 4:3 for pentaglyme and hexaglyme. Solid complexes were deposited also for hexaethylene glycol, but their compositions were not definitely determined. The solid complexes obtained here were all deliquescent. The deposition of the complexes was generally interfered with by water in the solution, and was not observed for some heavier lanthanoids when a small amount of water was present in the solution. The solubilities of the solid complexes with EO4 and EO5 increased with an increase in the atomic number of the lanthanoid, a fact suggesting a unique selectivity of the glycols. The infrared absorption bands of polyethylene glycols or glymes in the 1000–1150 cm−1 region became sharper upon the complexing of the glycols or glymes with lanthanoids; this sharpening can be explained by the change in the conformations in the ligand molecules.
  • Wakako Kanda, Masaaki Nakamura, Hisashi Okawa, Sigeo Kida
    1983 Volume 56 Issue 3 Pages 744-747
    Published: 1983
    Released: June 27, 2006
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    Binuclear iron(III) complexes Fe2(R-R′-sap)2(tcoq) have been prepared by the oxidation of binuclear iron(II) complexes Fe2(R-R′-sap)2 with tetrachloro-o-benzoquinone (TCOQ), where H2(R-R′-sap) represents 2-(salicylideneamino) phenols with the substituent R on the salicylaldehyde ring and the R′ on the o-aminophenol ring. Magnetic measurements indicated the operation of an intramolecular antiferromagnetic spin-exchange interaction between the iron(III) ions, the exchange integrals being evaluated at −6–−10 cm−1. In both polarograms and cyclic voltammograms of these complexes, two redox processes attributable to Fe(III)–Fe(III)\ ightleftharpoonsFe(III)–Fe(II)\ ightleftharpoonsFe(II)–Fe(II) were observed.
  • Jun Saito, Junji Hara, Shozo Toda, Shigeyuki Tanaka
    1983 Volume 56 Issue 3 Pages 748-752
    Published: 1983
    Released: June 27, 2006
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    Measurements were made of field desorption mass spectra of normal and deuterated styrene oligomers synthesized in various alkylbenzenes. Several series of molecular ion peaks are observed in both the spectra. From a comparison between them we have identified oligomers’ end groups and derived formation mechanisms for individual molecular species. It has been clarified that molecular species independent of solvents are produced through chain transfer of propagating radicals to styrene dimers. Analysis for the polymerization mechanism of styrene as well as characterization of polymer molecules has been successfully performed by field desorption mass spectrometry.
  • Shizen Sekiguchi, Noboru Tone, Toshio Takei, Noboru Tomoto
    1983 Volume 56 Issue 3 Pages 753-757
    Published: 1983
    Released: June 27, 2006
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    Reactions of 1-dimethylamino-2,4-dinitronaphthalene with potassium methoxide or ethoxide were carried out in DMSO–CH3OH or DMSO–C2H5OH (90:10 v/v), respectively, where the 1,3-disubstituted anionic σ complexes were first rapidly formed, undergoing isomerizations to the 1,1-disubstituted anionic σ complexes. Rates and activation parameters were determined by kinetic studies using stopped-flow and conventional spectrophotometers. The rate constant (25 °C) for the formation of 1,3-disubstituted one in DMSO–CH3OH is about half that in DMSO–C2H5OH, whereas the rate constant (25 °C) for its decomposition is more than twice that in DMSO–C2H5OH. The apparent pseudo-first-order rate constant for the formation of 1,1-disubstituted anionic σ complex in DMSO–CH3OH depends upon the methoxide ion concentration, whereas that in DMSO–C2H5OH is almost independent of the ethoxide ion concentration. The mechanism is discussed on the basis of activation parameters.
  • Hideo Tomioka, Norihiro Hayashi, Tsuneo Asano, Yasuji Izawa
    1983 Volume 56 Issue 3 Pages 758-761
    Published: 1983
    Released: June 27, 2006
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    Thermolysis and photolysis of 2-diazo-1,3-dicarbonyl compounds were investigated as a function of methanol concentration. As the methanol concentration decreased, methyl group migration increased concomitant with the suppression of O–H insertion into methanol, whereas aryl group migration was essentially unaltered with the methanol concentration. The results are interpreted as indicating that aryl migration occurs directly from the excited state of diazo compounds, but that met hyl migration takes place in the singlet carbene in competition with O–H insertion.
  • Hiroyoshi Kamogawa, Asami Kanzawa, Masahiro Kadoya, Takeshi Naito, Mas ...
    1983 Volume 56 Issue 3 Pages 762-765
    Published: 1983
    Released: June 27, 2006
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    Reins consisting of cross-linked poly(styrene-divinylbenzene) matrices functionalized with hydrazinosulfonyl groups react with aldehydes and ketones to form the sulfonylhydrazone derivatives. The extent of the reaction is sensitive to the type of resin and the bulk of the carbonyl compound. When heated strongly under alkaline conditions, the sulfonylhydrazones release the corresponding alkenes; upon the NaBH4 or LiAlH4 treatment, they also release the corresponding alkanes; and, upon refluxing in methanol with potassium cyanide, they release nitriles containing one additional carbon atom.
  • Hiroshi Fukui, Hidenori Kanehisa, Norio Ishibashi, Ichizo Miyake, Hide ...
    1983 Volume 56 Issue 3 Pages 766-769
    Published: 1983
    Released: June 27, 2006
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    A bitter heptapeptide BPIa was synthesized and compared with the natural peptide, isolated by Minamiura et al. from casein hydrolyzate, by means of thin layer chromatography, paper electrophoresis, and carboxymethylcellulose column chromatography. All results for the two peptides matched very closely each other. The synthetic BPIa has an extremely bitter taste with its threshold value 0.05 mM. It is one of the most bitter compounds such as phenylthiourea and quinine.
  • Seiji Shinkai, Youichiro Hara, Osamu Manabe
    1983 Volume 56 Issue 3 Pages 770-774
    Published: 1983
    Released: June 27, 2006
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    N-Hexadecylthiazolium bromide(HxdT) in the CTAB micelle, which is known as an excellent catalytic system for acyloin condensation of aldehydes, catalyzes the reverse reaction (i.e., retro-acyloin condensation) to give aldehydes from α-ketols via the active aldehyde intermediates. The existence of the novel, HxdT-mediated process was proposed on the basis of an experimental discovery that flavin (3-methyltetra-O-acetylriboflavin: MeFl), which is capable of oxidatively trapping the active aldehyde intermediates, is reduced by α-ketols such as acetoin and 3-hydroxy-3-methyl-2-butanone in the micellized HxdT solution. It was further substantiated by detection of acetaldehyde in the final reaction mixture. Based on the disappearance rate of the absorbance of MeFl, we spectrophotometrically estimated the rate constants for the retro-acyloin condensation. Similarly, biacetyl, the monohydrated species of which is analogous to α-ketol, afforded acetaldehyde and acetic acid in the micellized HxdT solution, the rate constant being greater by factors of 102–103 than those for α-ketols. The relevance of the retro-acyloin condensation to biological systems (e.g., the mechanism of transketolase catalysis) is discussed.
  • Naomi Ueda, Bunji Natsume, Kazumi Yanagiuchi, Yoshiteru Sakata, Toshia ...
    1983 Volume 56 Issue 3 Pages 775-779
    Published: 1983
    Released: June 27, 2006
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    New π-donors containing a pyrene or a tetrahydropyrene ring were synthesized by means of a unique transannular reaction of the corresponding [2.2]metacylcophane derivatives. The CT complexes of these donors with a series of TCNQ derivatives different in electron affinity were prepared, and their electrical conductivities on single crystals were measured. The highest conductivity (0.36 Ω−1 cm−1) was that of the tetrahydropyrene derivative-TCNQ complex. It was reconfirmed that the partial charge-transfer from a donor to an acceptor is very important for high conductivity.
  • Shigeo Nishimura, Yasuhiro Momma, Hideo Kawamura, Michio Shiota
    1983 Volume 56 Issue 3 Pages 780-783
    Published: 1983
    Released: June 27, 2006
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    Effects of the β-methyl group at C-10 and some oxygen functions (=O, OH, OAc) at C-11, C-17, and C-20 on the rates of hydrogenation of 3-oxo-4-ene steroids have been studied with palladium catalyst in pyridine or THF/HBr as solvent. In contrast to the hydrogenation in pyridine, the rate in THF/HBr was greatly depressed by the presence of 10β-methyl group. The reactivity of the steroids was enhanced by the oxygen functions, in particular, by 11, 17-dioxo group. The effects of the substituents are discussed from a mechanistic consideration based on the obtained results.
  • Takayuki Suga, Ym Sook Lee, Toshifumi Hirata
    1983 Volume 56 Issue 3 Pages 784-787
    Published: 1983
    Released: June 27, 2006
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    The biotransformation of c-4-p-menth-8(9)-en-r-l-ol (β-terpineol) and its acetate with the cultured suspension cells of Nicotiana tabacum were tested. It was found that the cultured cells have the ability to hydroxylate not only the allylic positions of the C–C double bond of these substrates, but also their terminal carbon-carbon double bond. The hydroxylation at the 4-position of their allylic positions was stereospecific, affording a trans-1,4-diol.
  • Masao Okubo, Hiroyuki Aratani, Takayuki Gond\={o}, K\={o}ji Koga
    1983 Volume 56 Issue 3 Pages 788-791
    Published: 1983
    Released: June 27, 2006
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    The reactions of p-methylphenyliminodimagnesium reagent (p-MeC6H4N(MgBr)2) with p- and m-dinitrobenzenes, bis(p-nitrophenyl) methane, bis(p-nitrophenyl) sulfide and ether, p- and m-nitrobenzaldehydes as well as 4-nitro-4′-methylbenzophenone were investigated. p-Dinitrobenzene, which is the strongest electron-acceptor among the substrates used, gave ca. 30% combined yield of bis(azoxy) and azoxy azo products. The oxidative coupling product, 4,4′-dimethylazobenzene, was isolated in 20–30% yields. About 60% combined yield of the bis(azoxy) and azoxy azo products was obtained in the same reaction with m-dinitrobenzene, which is less electron-accepting than the p-isomer. In the reaction of bis(p-nitrophenyl)methane, bis(p-nitrophenyl) sulfide and ether with five molar amounts of the reagent, ca. 70% combined yields of bis(azoxy), azoxy azo, and bis(azo) products were obtained. On the treatment of the nitrobenzaldehydes and the nitrobenzophenone, in contrast, the reaction took place exclusively on the nitro group. The results are discussed in terms of the electron-accepting ability of substrates.
  • Katsuhiro Kawashiro, Shiro Morimoto, Hideyuki Yoshida
    1983 Volume 56 Issue 3 Pages 792-795
    Published: 1983
    Released: June 27, 2006
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    The resolution of the six imino derivatives of glycine (Gly) by ion-exchange chromatography is described. The imino compounds included iminodiacetonitrile (1), iminodiacetamide (2), iminodiacetic acid (3), α-(cyanomethylamino)acetamide (4), α-(cyanomethylamino)acetic acid (5), and α-(carbamoylmethylamino)acetic acid (6). A mixture of 16 was chromatographed along with Gly, glycinamide, aminoacetonitrile, and NH3 with an automatic amino acid analyzer using Aminex A-4 resin column (0.25φ×50 cm) and sodium citrate buffers. When the initial buffer of pH 3.25 was changed to pH 6.50 15 min after beginning the analysis, these ten components were completely resolved. The analysis was completed in about 4.5 h. The stability of 1, 4, and 5 in aqueous media at room temperature was also studied.
  • Hidetoshi Iwamoto, Masaji Yoshimura, Takaaki Sonoda, Hiroshi Kobayashi
    1983 Volume 56 Issue 3 Pages 796-801
    Published: 1983
    Released: June 27, 2006
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    Anion-catalyzed phase-transfer catalysis was evidenced in the diazo-coupling reactions of the arenediazonium ion with a range of diazophile components in liquid-liquid- and liquid-solid two-phase systems. The tetrakis[3,5-bis(trifluoromethyl)phenyl]borate ion was effective as an anionic catalyst to accelerate the reactions. Comparisons of the reaction rates in the two-phase system with those in solution systems indicated that the acceleration was due to the increased activity of the cationic reagent, partly by solubilization and partly by the dehydration of such cationic species in the nonpolar organic phase.
  • Yoshio Okahata, Reiko Ando, Toyoki Kunitake
    1983 Volume 56 Issue 3 Pages 802-808
    Published: 1983
    Released: June 27, 2006
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    The reaction with water and amines of the azomethine moiety that is part of single-chain ammonium amphiphiles was examined. These amphiphiles form stable bilayer aggregates when they have the alkyl tail of C7 or C12. The reaction with water of the bilayer-forming amphiphiles ceases at the hydration stage and are 10–2000 times slower than those of the amphiphiles which do not form bilayers and undergo hydrolytic cleavage. The reactivity of the azomethine moiety in bilayers decreases with increasing distance from the membrane surface. The Arrhenius plots for the bilayer-forming amphiphiles show discontinuities at temperatures corresponding to phase transition of the respective bilayer (Tc). The apparent activation energy is larger at temperatures below Tc than at temperatures above Tc. This suggests that water penetration is facilitated in the fluid bilayer. The reaction with amines was affected by their solubility in the bilayer matrix, and poly(ethylenimine) gave a much reduced reaction rate when the azomethine moiety was buried deep in the bilayer matrix.
  • Gaku Yamamoto, Masahiko Suzuki, Michinori Oki
    1983 Volume 56 Issue 3 Pages 809-814
    Published: 1983
    Released: June 27, 2006
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    9-(1,1-Dimethyl-2-phenylethyl)-1,2,3,4-tetrahalotriptycenes (halogen=F, Cl, and Br) were synthesized and the kinetic studies of the rotational isomerization were made. The obtained data were compared with those for the corresponding 1-halo derivatives. The equilibrium constants (±scap) for the tetrahalo compounds are smaller than those for the respective monohalo counterparts. The tetrafluoro compound isomerizes twice slower than the monofluoro one at 240 °C, showing the “positive” buttressing effect. Contrarily, the tetrachloro and the tetrabromo compounds isomerize 13 and 100 times, respectively, faster than the corresponding monohalo compounds at 175 °C, exhibiting the “negative” buttressing effect. These intriguing phenomena are discussed in terms of the molecular deformation in these congested compounds, which affects both the ground state and the transition state for rotation.
  • Yoko Nambu, Takeshi Endo, Makoto Okawara
    1983 Volume 56 Issue 3 Pages 815-817
    Published: 1983
    Released: June 27, 2006
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    Acyl transfer reaction from N-benzyl-8-S-(p-nitrobenzoyl)dihydrolipoamide to benzylamine was enhanced with oxidizing agents such as cobalt(II) ion or a soluble flavin under an oxygen atmosphere or with di-4-pyridyl disulfide, accompanied by the formation of N-benzyllipoamide.
  • Yoshimasa Ishimura, Ken-ichi Maruya, Yoshiyuki Nakamura, Tsutomu Mizor ...
    1983 Volume 56 Issue 3 Pages 818-821
    Published: 1983
    Released: June 27, 2006
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    [NiBr(σ-C6F5)(PPh3)2] and [NiCl(σ-C6Cl5)(PPh3)2] are active for ethylene dimerization in the presence of AgClO4. The activity increases with increase in the amount of AgClO4 and reaches maximum at AgClO4/Ni-complex=2. Addition of excess AgClO4 leads to marked decrease in activity with [NiBr(σ-C6F5)(PPh3)2] but a little decrease with [NiCl(σ-C6Cl5)(PPh3)2]. 31P NMR spectra of the active solution showed new resonance peaks due to [Ni(ClO4)(σ-C6X′5)(PPh3)2] and [Ni(ClO4)(σ-C6X′5)(PPh3)] (X′=F,Cl), accompanying formation of AgX (X=Br,Cl) and [Ag(ClO4)(PPh3)]. Thus the role of AgClO4 is to abstract halide anion and/or triphenylphosphine. The amount of Ni(ClO4)(σ-C6X′5)(PPh3)] is in good correlation with the rate of dimerization, which suggests this species to be catalytically active.
  • Masahiro Kohno, Hiroaki Ohya-Nishiguchi, Kiyoko Yamamoto, Tosio Sakura ...
    1983 Volume 56 Issue 3 Pages 822-826
    Published: 1983
    Released: June 27, 2006
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    The electron-spin-resonance (ESR) spectra of three paramagnetic species trapped in single crystals of chloro(tetraphenylporphyrinato)cobalt(III) have been observed at 77 K. Using the ESR parameters obtained, one of them has been identified as the [CoIII(tpp)]2+·(Cl)2 π cation radical, and the other two species, as [CoII(tpp)] which are influenced by axial ligation. From the angular variations in the hfcc due to the 59Co, 14N, and 35Cl in the π cation radical, it has been found that the unpaired electron resides on the a2u porphyrin π orbital and polarizes the Co and Cl atomic orbitals through a spin-polarization mechanism. Finally, the radical formation mechanisms in solution are briefly discussed, based on the results obtained from the single-crystalline measurements.
  • Koichiro Miyajima, Masahiro Sawada, Masayuki Nakagaki
    1983 Volume 56 Issue 3 Pages 827-830
    Published: 1983
    Released: June 27, 2006
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    Viscosities of aqueous solutions of alkanoic acids including formic acid were measured by an Ostwald type viscometer at 15, 25, and 35 °C, and the viscosity B-coefficient and the temperature dependence of B-coefficient, dBdT, were calculated. From the signs and the magnitudes of Bst, increment of B-coefficient arising from the change of water structure, and dBdT, it was concluded that formic acid was a hydrophilic structure breaker, while acetic acid was neither a structure maker nor a structure breaker. Both propionic acid and butyric acid were the hydrophobic structure makers. The mechanism of structure breaking effect of carboxyl group was briefly discussed.
  • Masahiro Kobayashi
    1983 Volume 56 Issue 3 Pages 831-837
    Published: 1983
    Released: June 27, 2006
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    Self-consistent charge extended Hückel calculations for systems consisting of 1–3 CO molecules chemisorbed on 8-atom and 10-atom clusters of Ru and Pd are reported. The binding energies and overlap populations between Pd and C are always smaller than those between Ru and C. It was found that the multiple types of bondings between 2–3 CO and a surface metal atom were less stable for Pd than for Ru.
  • Tsutomu Masujima
    1983 Volume 56 Issue 3 Pages 838-845
    Published: 1983
    Released: June 27, 2006
    JOURNALS FREE ACCESS
    The overall conformational changes of the macromolecular complex between poly(α-L-glutamic acid), poly(Glu), and Cu(II) in 0.15 M NaCl were investigated by means of the light scattering method at three mixing ratios of Glu residues to Cu2+, R, (32, 16, and 8) in the pH range of 4–7. The root-mean-square radius of gyration and the weight-averaged molecular weight of poly(Glu) were determined by means of the Zimm plot, and those pH dependences show that the poly(Glu) shrinks in the course of the coil-to-helix transition and that it forms aggregates at pH values lower than 4.7, where helix formation is almost completed. In the presence of Cu2+ ions, the bound Cu(II) accelerates the shrinking of the poly(Glu) conformation and induces the aggregation in a high pH region, where the helix is imperfect. With the aid of theoretical treatments in the text, the aggregation scheme in the helix region was disclosed to be side-by-side, in which a 70–95% length of a helix overlaps one another. All these results and the pH dependence of the radius of gyration per poly(Glu) molecule were discussed in relation to the complex formation between Cu(II) and poly(Glu).
  • Masakatsu Ueno, Sh\={o}go I, Kiyoshi Shimizu
    1983 Volume 56 Issue 3 Pages 846-849
    Published: 1983
    Released: June 27, 2006
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    Cation transference numbers for 0.02 mol dm−3 KCl in 0-, 5-, 10-, 15-, 20-, and 30-mol% ethanol–water mixtures were determined by the moving boundary method at 25 °C up to 1500 kg cm−2 (1 kg cm−2=0.9807×105 Pa). The cation transference number, t+, initially increases with increasing ethanol content up to 10–15 mol% and then decreases at all the pressures studied. In water and ethanol–water mixtures below 20 mol%, t+ at the definite solvent decreases with increasing pressure. The decreasing rate becomes smaller as the ethanol content increases, and the tendency is reversed finally at 30 mol%. To account for the variation of t+ with solvent composition and pressure, specific interactions between the ions and solvent have been taken into consideration.
  • Koichi Hirano
    1983 Volume 56 Issue 3 Pages 850-854
    Published: 1983
    Released: June 27, 2006
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    The excited states of the organic dye anions of Uranine and Eosin Y are invesitigated by the semi-empirical SCF-MO-CI calculations. The two-center core integral values of the C–Br bond (−0.20 eV) were determined. Agreement between the calculated and observed spectra was satisfactory. The first intense bands of these dye anions can be assigned to the HOMO→LUMO transition band arising from the local excitation of xanthene ring. The second bands are interpreted as the overlap of the two transition bands for the xanthene ring and for the residual π-systems.
  • Osamu Ikeda, Hiroyuki Jimbo, Hideo Tamura
    1983 Volume 56 Issue 3 Pages 855-861
    Published: 1983
    Released: June 27, 2006
    JOURNALS FREE ACCESS
    The adsorption of tetramethylurea (TMU) at the mercury/water interface was studied by means of differential capacity measurements. TMU was found to take three different orientations, depending on the surface excess and the charge sign of the electrode. These orientations could not be explained simply by the orientation of the TMU dipole in the electric field or by the hydrophobic interaction between the methyl groups of TMU and the electrode, but it was explained on the basis of interactions between TMU and water molecules, and on the basis of the TMU molecules themselves in the adsorption layer and an electronic polarization effect of the nitrogen atoms in TMU. A few water-adsorption models were compared in an attempt to estimate the dipole moment of the TMU molecule at the interface.
  • Mamoru Ai
    1983 Volume 56 Issue 3 Pages 862-865
    Published: 1983
    Released: June 27, 2006
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    The effect of the difference in the oxidation state of the second component added to MoO3 on the generation of acidic sites was studied with regard to Sn2+—Sn4+, Fe2+—Fe3+, Cr3+—Cr6+, and Cu+—Cu2+. It was found that a markedly lager amount of acidic sites is generated by the combination of Sn2+, Fe2+, or Cr3+ with MoO3 than by that of Sn4+, Fe3+, or Cr6+ respectively. As a general feature of metal-oxide combination, it is proposed that the addition of a metal ion in a lower oxidation state to MoO3 brings about a markedly more significant acidity generation than that of a metal ion in a higher oxidation state. An explanation to account for the results was attempted in relation to the reducing function of the second component.
  • Yasuyuki Takeda
    1983 Volume 56 Issue 3 Pages 866-868
    Published: 1983
    Released: June 27, 2006
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    Limiting ionic molar conductivities (λ°) of 18-crown-6 (18C6) and dibenzo-18-crown-6 (DB18C6) complexes with K+ in several protic and aprotic solvents have been determined at 25 °C. The crystal ionic radius of 18C6 complex with K+ is nearly identical with that of tetrabutylammonium ion ((n-C4H9)4N+). For CH3OH, the mobility of the 18C6 complex with K+ is nearly equal to that of (n-C4H9)4N+. However, for H2O, the former is much larger than the latter, but the contrary is true for aprotic solvents. Walden products of 18C6 complexes with K+ for the solvents are nearly equal to each other. For acetonitrile and DMSO, the λ° value of the DB18C6 complex with K+ is smaller than those for the tetrapentylammonium ion ((n-C5H11)4N+) and for the tetraisopentylammonium ion ((i-C5H11)4N+). For nitrobenzene and propylene carbonate, that of the DB18C6 complex with K+ is smaller than those of (n-C5H11)4N+ and (i-C5H11)4N+, respectively. In contrast to the case of the aprotic solvents, the λ° value of the DB18C6 complex with K+ for CH3OH is nearly equal to those of (n-C5H11)4N+ and (i-C5H11)4N+. Walden products of the DB18C6 complexes with K+ for the solvents are nearly equal to each other. From the above data, it appears that a solute which contains a unit of 18C6 in its structure does not enforce a hydrogen-bonded structure for a protic solvent.
  • Tomohiro Ohta
    1983 Volume 56 Issue 3 Pages 869-872
    Published: 1983
    Released: June 27, 2006
    JOURNALS FREE ACCESS
    The mechanism of the title reaction is determined under steady state conditions by the irradiation of the mixtures of Cl2, CO, O2, and N2 at 300 K with black blue fluorescence lamps using infrared spectroscopy. The pressure dependence of the ratio of the formation rate of carbon dioxide to that of phosgene (COCl2) and the other results indicated that the oxidation of CO proceeded via intermediates ClCO and ClC(O)O2 as the termolecular process rather than the bimolecular oxidation by ClOO and/or ClO. The ratio of the competitive reactions of chloroformyl radicals, k8k9a, was found to be (6.5±0.4)×10−2 in the total pressure range from 30 to 755 Torr (1 Torr=133 Pa); ClCO+Cl2→COCl2+Cl (8), ClCO+O2→ClC(O)O2* (9a). And also, the ratio of the competitive reactions of the vibrationally excited intermediates, k9bk9c, was (3.4±0.3)×1018 molecule/cm3; ClC(O)O2*→ClCO+O2 (9b), ClC(O)O2*+M→ClC(O)O2+M (9c). The role of this reaction in the stratosphere is discussed and estimated to be unimportant.
  • Shunzo Katayama, Kazuko Tanaka, Reita Tamamushi
    1983 Volume 56 Issue 3 Pages 873-876
    Published: 1983
    Released: June 27, 2006
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    The conductance behavior of electrolyte mixtures was investigated for the systems of bivalent metal nitrates and sodium sulfate in aqueous solutions of high ionic strengths (I≥0.3 mol dm−3) at 25 °C. Significant deviations of the measured conductivities from the additivity were observed in all the systems, which can be attributed to the ion pair formation of the bivalent metal ion with sulfate ion. The conditional formation constants, Kc, were determined by means of computer analysis of the deviation; Kc-values at each ionic strength were found to decrease in the sequence Cd>Mn\simeqNi\simeqCo\simeqZn>Mg.
  • Haruo Nakayama
    1983 Volume 56 Issue 3 Pages 877-880
    Published: 1983
    Released: June 27, 2006
    JOURNALS FREE ACCESS
    Phase diagrams of the binary mixtures of tetrabutylammonium salt [(n-C4H9)4N]nX (X=NO2, NO3, BrO3, ClO3, IO3, ClO4, MnO4, and NCS for n=1; X=CO3, SO4, WO4, and CrO4 for n=2; and X=PO4 for n=3) with water were determined over the temperature range between −10 and +50 °C. From these diagrams the following results were obtained: (1) the formation of a clathrate-like hydrate for salts having such anions as NO2, NO3, BrO3, ClO3, IO3, SO42−, and PO43− was newly confirmed; (2) the melting point of the clathrate hydrate of the salt with monovalent anion was appreciably influenced by the kind of anion; (3) in the hydrates of the salt having either di- or trivalent anions, the melting points were relatively high and were only slightly affected by the kind of anion; (4) the crystal structure of these hydrates was essentially the same as that of the tetrabutylammonium fluoride hydrate, judging from the hydration numbers; (5) the solubilities in water of both permanganate and perchlorate were markedly lower than that of the iodide; and (6) in the thiocyanate system a phase separation into two liquid phases was observed at temperatures higher than +3.5 °C. The effect of a monovalent anion on the stability of the clathrate hydrate was discussed in connection with the conventional partial molal volume of the anion.
  • Yoshihiro Sasaki
    1983 Volume 56 Issue 3 Pages 881-887
    Published: 1983
    Released: June 27, 2006
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    The reactions of bis(α-diketone dioximato)iron(II) coordinated by two nitrogeneous base molecules (X) with carbon monoxide and benzyl isocyanide were studied kinetically in chloroform; here α-diketone dioxime=2,2′-difurylglyoxime (H2fr) and dimethylglyoxime (H2dg). The reactions proceeded reversibly through a dissociative mechanism. For the reaction Fe(Hfr)2(X)2\oversetk1\undersetk−1\ ightleftharpoonsFe(Hfr)2(X)+X, plots of logk1 vs. pKa (Ka : dissociation constant of conjugate acid of base) for pyridines gave a negative correlation. The logk1 values of 4-cyanopyridine and 4-acetylpyridine systems were smaller and that of 2,6-dimethylpyridine system larger than predicted by their pKa values. Imidazole and 1-methylimidazole were more inert than pyridines. For the reaction Fe(Hfr)2(X)+(CO)\oversetk2\undersetk−2\ ightleftharpoonsFe(Hfr)2(X)(CO), logk−2 vs. pKa plots for sterically unhindered pyridines showed a linear relationship, but the basicity of pyridine bases did not affect the CO dissociation processes very much. 2-Methylpyridine, 2,4-dimethylpyridine, and 2,6-dimethylpyridine facilitated the dissociation of CO slightly as compared with pyridine. Imidazole and 1-methylimidazole allowed CO to be more inert and piperidine more labile than pyridines. The dissociation of the base was significantly affected by the change of substituents in α-diketone dioxime, and the dissociation of CO was slightly affected by the change of substituents. The reaction behavior was discussed on the basis of the activation parameters and infrared data.
  • Masao Kiyama, Toshio Takada
    1983 Volume 56 Issue 3 Pages 888-890
    Published: 1983
    Released: June 27, 2006
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    An experimental study was made of the oxidation with air of alkaline suspensions containing needle-like Fe3O4 particles and slight amounts of Co1⁄3/Fe2⁄3(OH)2 at temperatures between 60 and 90 °C, together with the properties of the resulting oxidation products. It has been found that the Hc (coercivity) values of the products were greatly affected by both the excess NaOH concentration and the oxidation temperature—i.e., the two essential factors in determining the difference in the properties of a cobalt ferrite layer coated on the Fe3O4 particles, that these values increased with the heat treatment in vacuo of the products within the temperature range of 200 to 450 °C, without decreasing the saturation magnetization values, and that the Hc increment was mainly governed by the Co content.
  • Naohide Matsumoto, Akira Hirano, Akira Ohyoshi
    1983 Volume 56 Issue 3 Pages 891-894
    Published: 1983
    Released: June 27, 2006
    JOURNALS FREE ACCESS
    A new family of binuclear nickel(II) complexes with a terephthaloyl or isophthaloyl bridge have been prepared by the electrophilic substitution reaction of (11,13-dimethyl-1,4,7,10-tetraaza-10,12-cyclotridecadienato)nickel(II) (Ni(Me2[13]dienatoN4)]+) or (12,14-dimethyl-1,4,8,11-tetraaza-11,13-cyclotetradecadienato)nickel(II) ([Ni(Me2[14]dienatoN4)]+) containing a nucleophilic center at the γ-carbon and terephthaloyl chloride or isophthaloyl chloride. The complexes were characterized by elemental analyses, infrared spectra, 1H NMR spectra, electronic spectra, and conductivity measurements.
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