Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Volume 47 , Issue 10
Showing 1-50 articles out of 74 articles from the selected issue
  • Yoshihisa Suzuki, Setsuko Yatabe
    1974 Volume 47 Issue 10 Pages 2353-2359
    Published: 1974
    Released: March 27, 2006
    JOURNALS FREE ACCESS
    A further study of the isomerization of inosine (1a) in a dilute alkaline solution has revealed the formation of α-pyranbsyl isomer (4a) and its β-isomer (3a). Adenosine (1b) was isomerized at 130 °C for 12 hr at pH 10, giving α-furanosyl (2b) (2% yield), β-pyranosyl (3b) (11%), and the α-pyranosyl isomer (4b) (0.8%), respectively; 65% of the 1b also remained. 9-β-D-Ribopyranosyl-6-mercaptopurine (3c) was prepared through this reaction from the corresponding β-furanoside (1c). Arabinosyl or xylosyl purine nucleosides were also isomerized, whereas neither 2′-deoxy nor 2′-substituted nucleoside showed any clear evidence of isomerization. In conclusion, the purine base and the 2′-hydroxyl anion are essential to the alkaline isomerization of nucleosides. By means of NMR, both 4a and 4b were found to have a 1C conformation, while 3a and 3b have a Cl conformation.
  • Masahiro Nitta, Kazuo Aomura, Katsumi Yamaguchi
    1974 Volume 47 Issue 10 Pages 2360-2364
    Published: 1974
    Released: March 27, 2006
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    The alkylation of m-cresol with propylene was carried out over a γ-alumina catalyst in a flow system under atmospheric pressure. It was found that the composition of the thymol mixture thus obtained was greatly ortho-rich. It was also observed that the catalytic activity varied with the temperature and the atmosphere for the calcination of the catalyst, whereas the selectivity for thymol formation was almost constant at about 90% at the reaction temperature of 250 °C. It has been established that thymol can be obtained selectively by vaporphase alkylation over a commercial γ-alumina catalyst under appropriate reaction conditions. Furthermore, the active sites of γ-alumina for this reaction were investigated by the poisoning technique with acids and bases. It was suggested that, for the alkylation, the Lewis-acid sites (surface aluminum) and the adjacent acid sites (surface hydroxyl) are necessary. The mechanism of the alkylation on those sites is also discussed.
  • Hisashi Miyata, Mitsuhiko Minobe, Yutaka Kubokawa
    1974 Volume 47 Issue 10 Pages 2365-2368
    Published: 1974
    Released: March 27, 2006
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    The hydrogenation of acetone adsorbed and the dehydrogenation of isopropanol adsorbed on silica-supported nickel catalyst have been studied by following the changes of hydrogen pressure and the reaction products as well as the IR spectra of adsorbed species. It was found that the formation of isopropanol proceeds via a precursor composed of acetone and hydrogen. The activation energies of hydrogenation of acetone adsorbed and of dehydrogenation of isopropanol adsorbed were 11–13 and 4–8 kcal/mol, respectively. The activation energy of the desorption was 13 kcal/mol for isopropanol and 19 kcal/mol for acetone. From the results the potential energy change during the hydrogenation of acetone was determined.
  • Nagao Azuma, Hiroaki Ohya-Nishiguchi, Jun Yamauchi, Kazuo Mukai, Yasuo ...
    1974 Volume 47 Issue 10 Pages 2369-2375
    Published: 1974
    Released: March 27, 2006
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    Single-crystal ESR studies have been carried out on symmetrical triphenylverdazyl (TPV) doped in a diamagnetic 1,3,5-triphenylbenzene (TPB) crystal at room temperature. There have appeared seven pairs of fine-structure absorptions in addition to the hyperfine splittings. Three out of the seven pairs have been assigned as zero-field splittings due to radical pairs, while the other three pairs have been identified as from radical triads. The six fine structure tensors have been determined through the angular variation of the resonance-field separations. The structures of the pairs and triads of TPV were discussed on the basis of the fine structure tensors, the crystal structures of TPB and TPV, and the spin distribution in the radical molecule, assuming that the unit cell of the mixed crystal with the radical concentration of less than 11.1% is identical with that of the host crystal, TPB. Within the limits of the X-ray examination, this assumption was found to be reliable. It was found that the molecular planes in each species are almost parallel to the bc-plane and that all the C-phenyl rings lie in the c-direction.
  • Jiro Tanaka, Tohru Kishi, Masashi Tanaka
    1974 Volume 47 Issue 10 Pages 2376-2381
    Published: 1974
    Released: March 27, 2006
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    The electronic absorption and emission spectra of α and β forms of perylene have been investigated. The lowtemperature spectra have been studied with the (001) plane, and adetailed vibrational analysis is presented. The reflection measurements with the (001) plane and the (110)or (1\bar10) plane are carried out, and the Kramers-Kronig transformation is carried out in order to obtain the absorption coefficient. The results present reasonable evidence for the existence of the intermolccular CT transition in the 27000 cm−1 region. The emission spectra at 4.2 K present several novel features of the mechanism of a monomer-like emission of the α-crystal.
  • Michiro Hayashi, Hisae Imaishi, Kazunori Kuwada
    1974 Volume 47 Issue 10 Pages 2382-2388
    Published: 1974
    Released: March 27, 2006
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    The microwave spectra of trans-ethanethiol and its isotopic species were measured. The rs structure of the trans isomer was determined from the observed moments of inertia. The trans isomer has a symmetrical CH3group, the parameters for the CH2SH part of the molecule being approximately equal to those of methanethiol. The C-C bond length, found to be 1.529±0.006Å, is close to that of propane. The angle α(CCS), obtained as 108°34′±19′, is much smaller than that of analogous molecules. Discussion is given for this anomalously small α(CCS) angle. From the Stark shifts, the dipole moment of the trans isomer was determined to be μa=1.058±0.023, μb=1.146±0.002 and μtotal=1.560±0.032 D, an angle of 28°46′ being made with the bisector of the α(CSH) angle inclining towards the ethyl group. Since the dipole moment of methanethiol makes an angle of 18°30′ with the bisector of the α(CSH) angle, the increase of the angle with the bisector for ethanethiol was concluded to arise from the induction moment of the ethyl group. A brief description is given for the spectra due to the gauche isomer.
  • Yoshitsugu Hasegawa, Isao Tomita
    1974 Volume 47 Issue 10 Pages 2389-2392
    Published: 1974
    Released: March 27, 2006
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    The distribution coefficients of Ag+, Tl+, K+, NH4+, Mg2+, Ca2+, Sr2+, Ba2+, Co2+, Zn2+, Y3+, and Ce3+ have been determined on a crystalline zirconium phosphate ion-exchanger in chloride solution media, and the affinity sequences are presented. pH titration curves and X-ray powder diffraction data were obtained for calcium and barium ions. The ion-exchange capacity of the exchanger for barium ions was found to be 4.4 meq/g, but the X-ray powder patterns were rather unusual as compared to those of other ions studied previously.
  • Takaji Yasui, Hiroshi Kawaguchi, Zenjiro Kanda, Tomoharu Ama
    1974 Volume 47 Issue 10 Pages 2393-2397
    Published: 1974
    Released: March 27, 2006
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    Some binuclear and trinuclear complexes containing μ-L-aminocarboxylato ligands, (+)D- and (−)D-[en2-Co(OCOCH(NH2)(CH2)nCOO)Co(OH2)en2](ClO4)4, (+)D-[en2Co(OCOCH(NH2)(CH2)nCOO)Co(NH3)5]-(ClO4)4 and (+)D- and (−)D-[en2Co{(OCOCH(NH2)(CH2)nCOO)Co en2}2](ClO4)5 (n=1 for L-aspartato and n=2 for L-glutamato), have been newly prepared. The structure and vicinal CD effect of these complexes were discussed on the basis of their absorption, 13C NMR and CD spectra data. Their geometrical structures were assigned as cis to the μ-L-aminocarboxylato-OH2 binuclear complexes (with respect to the β-COO or γ-COO end of μ-aminocarboxylato bridge and the aquo ligand), and as trans to the di-μ-L-aminocarboxylato trinuclear complexes (with respect to the β-COO or γ-COO ends of two μ-aminocarboxylato bridges).
  • Taichi Negi, Takahiro Kaneda, Hiroshi Mizuno, Toshihiro Toyoda, Yoshit ...
    1974 Volume 47 Issue 10 Pages 2398-2405
    Published: 1974
    Released: March 27, 2006
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    Novel cyclic 1,2,3,4,5-hexapentaene compounds were synthesized from cyclic diyne-diol IX via diallene-dibromide X in order to study transannular electronic interaction. A diallene-dibromide Xc-I obtained from a diyne-diol isomer IXc-I was debrominated with active zinc to give cyclic hexapentaene IIc, whereas the other diallene-dibromide Xc-II derived from the second diyne-diol isomer IXc-II was not. The X-ray crystallographic analysis of the dibromide Xc-I was then carried out, and the s-trans structure was assigned to the dibromide. On the basis of this result, the stereochemistry of the transformation from diyne-diol to the hexapentaene group was discussed. The electronic spectrum of a cyclophane IIa containing the hexapentaene group showed a transannular π-electronic interaction between the benzene ring and the hexapentaene group, unlike those of the other hexapentaene derivatives, IIc and XV.
  • Kiyonori Shinoda
    1974 Volume 47 Issue 10 Pages 2406-2409
    Published: 1974
    Released: March 27, 2006
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    Co-pyrolysis of chloroethanes and methanol on activated alumina was carried out in order to elucidate the reaction mechanism. The reaction rate was of first order in chloroethanes in the presence of excess methanol. A linear free energy relationship was found to exist between the reactivities of chloroethanes (at 230°C) and Taft’s σ* constants, ρ* values for reactions of RCH3, RCH2Cl and RCHCl2 series were 0.24, 0.45 and 0.70, respectively. It could be assumed that a β-hydrogen of chloroethanes was abstracted by the nucleophilic attack of methanol, chlorine being removed at the same time. E2 reaction seems to dominate in co-pyrolysis of chloroethanes and methanol on activated alumina.
  • Kazuo Sakane, Yoshio Otsuji, Eiji Imoto
    1974 Volume 47 Issue 10 Pages 2410-2414
    Published: 1974
    Released: March 27, 2006
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    Treatment of 4-nitrol,3-indandione (1) with an equivalent of ethylene glycol in benzene in the presence of p-toluenesulfonic acid afforded 4-nitro-1,3-indandione-1-ethylene acetal (2), 3-ethylene acetal (3) and 1,3-bisethylene acetal (4). Kinetic studies revealed that 2 is a kinetically preferred product and 3 is a thermodynamically preferred product. However, the reaction of 4-acetamido-1,3-indandione (5) with ethylene glycol under similar conditions gave 4-acetamido-1,3-indandione-1-ethylene acetal (6) as a product both kinetically and thermodynamically controlled. Thioacetalization of 1 with an equivalent of 1,2-ethanedithiol afforded selectively 4-nitro-1,3-indandione-1-ethylene thioacetal (9).
  • Mikio Nakamura, Michinori Oki, Hiroshi Nakanishi, Osamu Yamamoto
    1974 Volume 47 Issue 10 Pages 2415-2419
    Published: 1974
    Released: March 27, 2006
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    Several 9-methyltriptycene derivatives have been synthesized and the PMR spectra examined at low temperatures. The compounds which have a methoxy or a methyl group at a peri position showed only broadening of methyl signals, whereas those with a chlorine at a peri position and another substituent at some other peri position showed a splitting of methyl signals. The compounds which have a halogen atom at a peri position are the intermediary cases in a sense that they show separation of the signal into two with 1 : 2 relative intensities but fail to show fine splittings. Activation parameters for the rotation were obtained by total line shape analysis. Substituent effects have been discussed.
  • Shun-ichi Murahashi, Kazuo Okumura, Yusuke Maeda, Akio Sonoda, Ichiro ...
    1974 Volume 47 Issue 10 Pages 2420-2425
    Published: 1974
    Released: March 27, 2006
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    endo-Tricyclo[3.2.1.02,4]octan-8-ylidene (2) generated by the thermolysis of sodium salt of endo-tricyclo[3.2.1.02,4]octan-8-one tosylhydrazone (5) gave toluene (3.9%), cyclohepta-1,4-diene(6, 14%), cyclohepta-1,3-diene(7, 3.5%), bicyclo[3.3.0]octa-1,6-diene(8, 4.8%), bicyclo[3.3.0]octa-1,7-diene(9, 9.0%), and endo-tricyclo[3.2.1.02,4]octane (10, 21%). In sharp contrast, exo-tricyclo[3.2.1.02,4]oct-8-ylidene (1) gave toluene (1.5%) and tricyclo[5.1.01,7]oct-5-ene (14, 57%). The results indicate significant homoconjugative interaction between the p-orbital of the divalent carbon and the symmetric Walsh orbital of the cyclopropane. This is in line with the results of 7-norbornenylidene (3) in which the interaction between the divalent carbon and the carbon-carbon double bond stabilizes the nonclassical methylene. Thermolysis of sodium salt of 7-norbornenone tosylhydrazone (18) gave rise to cyclohexa-1,3-diene (3%), norbornene (6%), toluene (5%), spiro[2.4]hepta-4,6-diene (19, 10%), and bicyclo[3.2.0]hepta-1,6-diene (21, 56%).
  • Kunio Okamoto, Koichi Komatsu, Masami Fujimori, Sumio Yasuda
    1974 Volume 47 Issue 10 Pages 2426-2430
    Published: 1974
    Released: March 27, 2006
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    A series of substituted phenyltropylium (I) and n-alkyltropylium ions (II) has been synthesized, and the kinetic measurements for the one-electron reduction of these ions have been carried out with Cr(II) in 10% HCl at 25°C. A linear correlation is observed between the logk2 values, for I (X-C6H4-C7H6+, X=p-OH, p-OCH3, p-CH3, H, p-Cl, p-Br, p-CN, m-OCH3) and for II (CnH2n+1-C7H6+, n=0,1–6), and the transition energy of the charge-transfer band of these ions, with pyrene as a donor. In addition, the values of logk2 for I exhibit a good linear free-energy relationship with pKR+ and also with the σ -value (ρ=+1.31), but not with σ+. The n-alkyl group is shown to diminish the reducibility of the tropylium ion, and a slight alternation effect of the length of the n-alkyl chain on the K2’s is observed.
  • Kunio Okamoto, Koichi Komatsu, Osamu Sakaguchi
    1974 Volume 47 Issue 10 Pages 2431-2436
    Published: 1974
    Released: March 27, 2006
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    A series of hetero-substituted tropylium salts (X-C7H6+·Y), including three new compounds, have been synthesized. Their relative reactivities in one-electron reductions with zinc powder have been determined by the use of a competitive-reaction method, which gave the following reactivity sequence: CH3O-C7H6+ (krel.=0.0295), t-C4H9-C7H6+ (0.146), CH3S-C7H6+ (0.255), C7H7+ (1.00), C6H5-C7H6+ (2.50), (C6H5)3Si-C7H6+ (7.50), Cl-C7H6+ (16.8), CH3OCO-C7H6+ (35.7), NC-C7H6+ (163). The values of logkrel. for the t-C4H9, H-, and C6H5-C7H6+ ions exhibit a good linear relationship with those of logk2 in the chromous-ion reduction. A linear correlation is also observed between logkrel. and the transition energy for the charge-transfer band of the respective cations, with pyrene as a donor. A plot of logkrel. against σp (for the ring substituent, X) gives a greater ρ-value (+4.0) than in the case of X-C6H4-C7H6+ (+1.31), reflecting the influence of the direct substitution on the tropylium ring.
  • Hitoshi Takeshita, Akira Mori, Shumei Ohta
    1974 Volume 47 Issue 10 Pages 2437-2439
    Published: 1974
    Released: March 27, 2006
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    Singlet oxygen was allowed to react with three 3-hydroxypyridine derivatives, I, II, and III, in order to investigate its general behavior toward dipolar substrates. The occurrence of an easy C=C cleavage process to give furanones (V and XI) through the dioxetones was a characteristic feature. In addition, maleimides (IV and IX), oxamates (VIII, XII and XIV), and a carbamate (XIII) were isolated as highly oxidized products.
  • Akira Takeda, Sadao Tsuboi, Takashi Sakai
    1974 Volume 47 Issue 10 Pages 2440-2443
    Published: 1974
    Released: March 27, 2006
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    The reaction of 2-chloro-2-methylpropanal with benzoylacetonitrile in aqueous K2CO3 has been studied. When 2-chloro-2-methylpropanal was added to a stirred suspension of benzoylacetonitrile in aqueous K2CO3, 2-hydroxy-3,3-dimethyl-4-cyano-5-phenyl-2,3-dihydrofuran (7) was obtained. The oxidation of 7 with CrO3gave α,α-dimethyl-β-cyano-γ-phenyl-Δβ,γ-butenolide (8). When benzoylacetonitrile was added to a suspension of 2-chloro-2-methylpropanal in aqueous K2CO3 stirred beforehand for 60 min, the reaction proceeded in a different manner to give the enol tautomer (9b) of 2,4-dibenzoyl-3-(α-hydroxyisopropyl)glutaronitrile (9a) at room temperature, and 2,2-dimethyl-3-(α-carbaminophenacyl)-4-cyano-5-phenyl-2,3-dihydrofuran (11) at 80–90 °C. The alkaline hydrolysis of the nitrile 9 conducted at 70 °C also afforded the amide 11. The nitrile 9 eliminated one mol of benzoylacetonitrile on treatment with H2SO4 to afford 2,2-dimethyl-3-hydroxy-4-cyano-5-phenyl-2,3-dihydrofuran (12). Chromic acid oxidation of 12 gave 2,2-dimethyl-3-oxo-4-cyano-5-phenyl-2,3-dihydrofuran (14), which can be derived from bullatenone in two steps. Structures of compounds 11, 12, and 14, which all possess 2,2-dimethyl-4-cyano-5-phenyl-2,3-dihydrofuran ring, have been confirmed and well correlated by both chemical transformations and spectral data.
  • Takayuki Kawashima, Naoki Inamoto
    1974 Volume 47 Issue 10 Pages 2444-2448
    Published: 1974
    Released: March 27, 2006
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    Aryliminotriphenylphosphoranes reacted with methanesulfonyl, ethanesulfonyl and α-toluenesulfonyl chlorides in the presence of triethylamine to give 1 : 2 adducts [α-(N-alkanesulfonyl-N-arylsulfamoyl)alkylidenephosphoranes] and the decomposition products, instead of 1 : 1 adducts [α-(N-arylsulfamoyl)alkylidenephosphoranes). They were obtained under ice-cooling, the structure being of betaine type. In the case of methanesulfonyl chloride, isomeric 1 : 2 adduct [α-(N-arylsulfamoyl)methanesulfonylmethylenephosphorane] was also obtained. 2-Propanesulfonyl chloride gave N-triphenylphosphonio-N-arylsulfamate instead of expected adduct. In the absence of triethylamine, α-(N-arylsulfamoyl) alkyltriphenylphosphonium chlorides were obtained in good yields. Possible mechanisms of these reactions have been discussed.
  • Tateki Emoto, Hideyuki Gomi, Masaaki Yoshifuji, Renji Okazaki, Naoki I ...
    1974 Volume 47 Issue 10 Pages 2449-2452
    Published: 1974
    Released: March 27, 2006
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    Lithium diphenylphosphinylide or diphenylphosphinothioylide ([Ph2PX]Li; X=O, S), prepared from diphenylphosphine oxide or sulfide and n-butyllithium, reacted with methyl iodide, acetaldehyde and benzaldehyde to give the corresponding phosphine oxides or sulfides in good yields, indicating the formation of C–P bond. Formation of [Ph2PS]MgCl from diphenylphosphinothioyl chloride (1) and magnesium was confirmed by the similar reactions. When 1 was allowed to react with magnesium or sodium for a long time, diphenylphosphides ([Ph2P]M) were produced by desulfurization, together with [Ph2PS]M (M=MgCl, Na). Reaction of 1 with [Ph2PS]M gave tetraphenyldiphosphine disulfide through formation of P-P bond, while diphenylphosphinyl chloride and [Ph2PO]M reacted through formation of P–O bond. The difference has been explained by soft-hard-acid-base concept.
  • Koshiro Goda, Hideyuki Gomi, Masaaki Yoshifuji, Naoki Inamoto
    1974 Volume 47 Issue 10 Pages 2453-2456
    Published: 1974
    Released: March 27, 2006
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    Reactions of [Ph2PO]M with benzaldehyde gave benzyl benzoate and benzyldiphenylphosphine oxide (3) in the case of M=Na, 3, α-hydroxybenzyldiphenylphosphine oxide, benzyl alcohol, benzoin and benzil in the case of M=MgCl, and 3 in the case of M=ZnCl. Reactions of [Ph2PX]M with p-benzoquinone gave 2,5-dihydroxyphenyldiphenylphosphine oxide or sulfide and p-hydroxyphenyl diphenylphosphinate in the cases X=O, S and M=Li, MgCl, Al, and 1,4-phenylene bis(diphenylphosphinate) or bis(diphenylphosphinothioate) in the cases X=O, S and M=FeCl. The reaction mechanisms have been discussed.
  • Michinori Oki, Tadashi Sugawara, Hiizu Iwamura
    1974 Volume 47 Issue 10 Pages 2457-2462
    Published: 1974
    Released: March 27, 2006
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    Conformational analysis of 1,3,5-trithiane derivatives with sulfur-substituents was carried out with the aid of PMR spectra at various temperatures. 2-Phenylthio-1,3,5-trithiane exhibited the strong anomeric effect whereas 2-phenylthiothiane the moderate. This enhanced anomeric effect in trithiane derivatives was attributed to both the stabilization of the axial form and the destabilization of the equatorial form. cis-2,4-Bis(phenylthio)-1,3,5-trithiane was found to possess a diaxial conformation to a fair extent in support of the presence of the strong anomeric effect. Equilibration between cis and trans forms of 2,4-bis(phenylthio)-1,3,5-trithiane was carried out to show that the trans form was more stable than the cis. The barrier to inversion of trans-2,4-bis(phenylthio)-1,3,5-trithiane was obtained as ca. 11 kcal/mol.
  • Tsuneo Suga
    1974 Volume 47 Issue 10 Pages 2463-2465
    Published: 1974
    Released: March 27, 2006
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    Als Fortsetzung früherer Mitteilungen, in welchen der Autor auf die oxydative Wirkung der Oxydationsprodukte des Hydrochinons bei der Lithentwicklung hinwies, wurde hier der Oxydationseffekt eingehender untersucht und der Mechanismus der Lithentwicklung diskutiert, obwohl einige Arbeiten keinen Oxydationseffekt vertreten. Die Lithentwicklung hat eine beträchtliche Induktionsperiode, in der man keine Schwärzung bemerken kann. Durch physikalische Entwicklung, die der chemischen Entwicklung und dem Fixieren nachfolgte, bemerkte man eine sichtbare Schwärzung. Diese Versuchsmethode führte zu folgenden Ergebnissen. Während der Induktionsperiode konnte man das Wachstum von Entwicklungskeimen experimentell finden. Der Oxydationseffekt angesammelter Oxydationsprodukte auf die Entwicklungskeime wurde im Entwicklungsverlauf nach der Induktionsperiode als wirksam betrachtet. Während der Induktionsperiode wurde aber eine Oxydation der Entwicklungskeime durch die diffundierenden Oxydationsprodukte als Saumeffekt beobachtet. Durch die Feststellung des Oxydationseffekts ist die Folgerung über den Mechanismus der Lithentwicklung die gleiche wie in früheren Arbeiten, kann aber ausführlicher beschrieben werden.
  • Takeshi Kotanigawa
    1974 Volume 47 Issue 10 Pages 2466-2468
    Published: 1974
    Released: March 27, 2006
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    As a result of a series of studies, ZnO–Fe2O3 catalysts have been shown to promote the selective methylation (k1) of phenol at the ortho position and also to promote the decomposition of methanol (k2). The activation energies were determined to be 22±2 kcal/mol for the methylation and 27 ±3 kcal/mol for the decomposition. The selectivity factor (S=k1k2) of the simultaneous reaction was determined for five types of catalysts in order to estimate the most favorable catalyst for the methylation. The selectivity factor of these catalysts decrease with the rise in the calcination temperature. For example, the S on the catalysts calcined at 500 °C is approximately at unity but the S on the catalysts calcined at 800 °C is at about 0.4. These results suggest that the calcination using the present catalysts should be controlled at a low temperature.
  • Yoshihisa Suzuki
    1974 Volume 47 Issue 10 Pages 2469-2472
    Published: 1974
    Released: March 27, 2006
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    The rate constants of the decrease in inosine at several temperatures between 50 °C and 140 °C in water were determined over the pH range from 1 to 13. They can be expressed as a sum of four simultaneous bimolecular reactions. Their thermodynamic parameters were obtained.
  • Masuzo Nagayama, Osamu Okumura, Katsumi Yaguchi, Akira Mori
    1974 Volume 47 Issue 10 Pages 2473-2475
    Published: 1974
    Released: March 27, 2006
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    2-Dimethylsulfonioalkane-1-sulfonates were formed by the reaction of α-olefins with the dimethyl sulfide-sulfur trioxide complex. The treatment of these products with alkali gave Δ1-alkene-1-sulfonates quantitatively. In the reaction between 1,2-epoxyalkanes and the dimethyl sulfide-sulfur trioxide complex, 1-dimethylsulfoniomethyl-1-alkyl sulfate was formed exclusively. 1-Dimethylsulfonio-1-alkenes were quantitatively formed upon the treatment of these products with alkali. The chemical structures of these compounds have been established, and the reaction routes were discussed.
  • Takeshi Takemura, Masayuki Aikawa, Hiroaki Baba
    1974 Volume 47 Issue 10 Pages 2476-2481
    Published: 1974
    Released: March 27, 2006
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    The mechanism of triplet-triplet (T-T) energy transfer in fluid solution has been studied by means of phosphorimetry in the temperature range 0–60 °C with acetophenone as energy donor, 1,4-dibromonaphthalene as acceptor and isooctane, isopentane or carbon tetrachloride as solvent. From the temperature dependence of the energy transfer, α and kdif could be evaluated separately, kdif denoting the diffusion-controlled rate constant for the encounter of donor and acceptor molecules and αkdif corresponds to the rate constant for the overall energy transfer reaction. The α values are 0.28 at 25 °C in isopentane and 0.43 at 21 °C in isooctane, indicating that the T-T energy transfer process is not strictly diffusion-controlled. The kdif values are nearly equal to those predicted by a modified Debye equation.
  • Masayuki Nakagaki, Noriaki Funasaki
    1974 Volume 47 Issue 10 Pages 2482-2485
    Published: 1974
    Released: March 27, 2006
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    The surface pressure-area curves of mixed monolayers of triolein and tricaprylin and the equilibrium spreading pressures of these liquid mixtures were measured at 25 °C. The surface pressures of the monolayers of the pure components, triolein and tricaprylin, did not vary when the monolayer was compressed below its collapse area, but the surface pressure of their mixed monolayers increased with the compression; the surface pressure at a zero area agreed well with the value of the equilibrium spreading pressure. From the two curves, the one representing the relation between the collapse pressure and the composition of the mixed monolayer, and the other representing the relation between the equilibrium spreading pressure and the composition of the liquid mixture, the compositions of the mixed monolayer and the liquid mixture coexisting in the equilibrium were obtained. Consequently, it was found that the component whose collapse pressure was lower was richer in the liquid mixture than in the mixed monolayer, while the other component, whose collapse pressure was higher, was poorer in the liquid mixture than in the mixed monolayer. It was concluded, on the basis of the phase rule and thermodynamics for a plane interface, that triolein and tricaprylin form a regular mixture in the monolayer as well as in a liquid.
  • Michio Hirota, Yoshio Umezawa, Hiroyuki Kojima, Shizuo Fujiwara
    1974 Volume 47 Issue 10 Pages 2486-2489
    Published: 1974
    Released: March 27, 2006
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    The on-line Fourier analysis of the AC polarographic current was found to give accurate results for electrode kinetics provided that the compensation of the iR drop and of the non-faradaic current was attained: The iR drop was compensated by a positive feedback technique. The charging current was cancelled by addition of a pseudo-charging current, inverse in phase to the former. Both the phase angles and amplitudes of the fundamental and second harmonic AC responses for the system of Pb(II) in 1M NaClO4 ([H+]=12 mM) agreed with theoretical prediction. As an illustration, the kinetic parameters of Cd(II)-1 N Na2SO4 system have been determined to be ks=(0.20±0.03) cm/s and α=0.30 (0.27<0.30<0.35) from the second harmonic AC polarogram.
  • Mutsuo Kodama
    1974 Volume 47 Issue 10 Pages 2490-2492
    Published: 1974
    Released: March 27, 2006
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    The rates and the mechanisms of the dissociation reactions of the Co(II)-EDMA complex in a phosphate buffer solution and the Ni(II)-EDDA complex in an ethylenediaminediacetate solution were studied by analyzing their kinetic waves by means of conventional DC polarography. The dissociation of the Co(II)-EDMA complex gave this rate law: −d[Co(II)-EDMA]⁄dt=kp·[Co(edma)+]·[H2PO4]. On the other hand, the dissociation of the Ni(II)-EDDA complex was found to proceed through a reaction mechanism which involves ligandolysis, corresponding to this rate law: −d[Ni(edda)0]⁄dt=k0×[Ni(edda)0]. On the basis of the relative rate constant, the detailed reaction mechanism was discussed. In the dissociation of the Co(II)-EDMA complex, the phosphate anion acts just as a proton donor. In the case of the Ni(II)-EDDA complex, the ligandolysis of the coordinated water has a profound effect on the dissociation rate of the edda2− anion from the nickel (II) ion.
  • Akira Kishioka, Masanori Haba, Michio Amagasa
    1974 Volume 47 Issue 10 Pages 2493-2496
    Published: 1974
    Released: March 27, 2006
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    Glass formation was investigated in the Na2O–TiO2–P2O5, K2O–TiO2–P2O5, BaO–TiO2–P2O5,Na2O–BaO–P2O5, and Na2O–BaO–TiO2–P2O5 systems. In the Na2O–TiO2–P2O5 system, glass containing up to 45.5 mol% TiO2 was found to be formed at the composition of Na2O/P2O5=1, whereas in the K2O–TiO2–P2O5 system the glass formation was observed in a narrow region along the composition of K2O/P2O5=1 in a three-component diagram. In the BaO–TiO2–P2O5 system, only the glass containing about 10 mol% TiO2 as a maximum was obtained. In the Na2O–BaO–TiO2-P2O5 system, the region of glass formation extended with an increase of Na2O up to 30 mol%. These results suggested that a certain amount of Na2O is necessary for the formation of glass containing a large amount of TiO2 in the presence of BaO. The three-component diagrams of the Na2O–TiO2–P2O5 and Na2O–BaO–P2O5 systems indicated that the most favorable amount of Na2O for the glass formation in this four-component system is 27 to 28 mol%.
  • Hiromu Imai, Tadamasa Ota
    1974 Volume 47 Issue 10 Pages 2497-2501
    Published: 1974
    Released: March 27, 2006
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    Physical and chemical properties of manganese(II), cobalt(II), nickel(II), copper(II) and zinc(II) chelates of acetoacetylferrocene were investigated. The solubility decreased in the order CHCl3>CH2Cl2>C6H5Cl>C6H4(CH3)2>C6H6, the chelates being more soluble in pyridine. It was found from magnetic data that the configuration is octahedral for the aquo or pyridine adduct of manganese(II), cobalt(II) and nickel(II) chelates, square planar for anhydride of copper(II) chelate, distorted octahedral for its pyridine adduct, and quasi-tetrahedral for the anhydride of manganese(II) chelate. The d-d transition of electronic spectra was analysed by Ohsymmetry for cobalt(II) and nickel(II) chelates, and by C2h symmetry for copper(II) chelate. Assignment of the d-d transition for manganese(II) chelate was difficult.
  • Hitoshi Shoji, Hisao Mabughi, Nobufusa Saito
    1974 Volume 47 Issue 10 Pages 2502-2507
    Published: 1974
    Released: March 27, 2006
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    The hydrolysis of antimony(III) ions was investigated through solvent extraction with dithizone–carbon tetrachloride solutions. In a 3 M (H, Na)ClO4 solution, a tracer concentration of antimony(III) (<10−8M) was found in the form of a monovalent cation, Sb(OH)2+ or SbO+, and a neutral species, Sb(OH)3 or SbO(OH). The former is predominant in strongly acidic media, while the latter becomes abundant in the weakly acidicto-neutral region. One of the constants of successive hydrolysis, K1=[Sb(OH)2+][Sb(OH)3]−1[H+]]−1, was calculated from the distribution ratios, giving the result: logK1=1.236±0.06. The chemical composition of the extracted species was estimated to be Sb(HDz)3.
  • Akihiko Yamashita, Katsuo Hara, Shigeko Aizawa, Minoru Hirota
    1974 Volume 47 Issue 10 Pages 2508-2510
    Published: 1974
    Released: March 27, 2006
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    The stable conformations of α-alkyl- and α,α-dialkyl-o-methoxybenzyl alcohols were deduced by measurement of their infrared and PMR spectra. Population of these conformations was estimated from the intensities of the O–H stretching bands of the free and the hydrogen-bonded species. The O–H chemical shifts at infinite dilution (δOH) of the free and the hydrogen-bonded species were determined by plotting the δOH values against population obtained from the infrared spectra. An anomalous behavior was observed with the α-alkyl-α-t-butyl alcohols, which might be due to a buttressing effect.
  • Akira Arase, Yuzuru Masuda, Akira Suzuki
    1974 Volume 47 Issue 10 Pages 2511-2514
    Published: 1974
    Released: March 27, 2006
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    The reactions of trialkylboranes with ferric chloride and thiocyanate in an aqueous tetrahydrofuran solution give the corresponding alkyl chlorides and thiocyanates in good yields. It was found that two equivalents of ferric salts per alkyl group of organoborane are required, and not only the first alkyl group of trialkylborane but other alkyl groups are also used.
  • Kazuo Sakane, Shinichi Oda, Eiichi Haruki, Yoshio Otsuji, Eiji Imoto
    1974 Volume 47 Issue 10 Pages 2515-2518
    Published: 1974
    Released: March 27, 2006
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    The Birch reduction of acenaphthene (1) followed by treatment of the reduction product with sodium ethoxide gave 2a,3-dihydroacenaphthene (3). The oxidation of 3 with hydrogen peroxide gave 2a,3,4,5-tetrahydroacenaphthene-4,5-diol (5). Further oxidation of 5 afforded various 1,7-disubstituted indan derivatives including 7-carboxyindan-1 -acetic acid (7). Two tricyclic N-heterocyclic compounds, 3,3a-dihydrocyclopent[de]quinolin-2(1H)-one (13) and 3,3a-dihydrocydopent[de]isoquinolin-1(2H)-one (17), were synthesized from 7.
  • Kikumasa Sato, Seiichi Inoue, Masao Ohashi
    1974 Volume 47 Issue 10 Pages 2519-2522
    Published: 1974
    Released: March 27, 2006
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    A New synthesis of 2-hydroxy-3-methyl-2-cyclohexen-1-one (Ia), a flavor component of coffee aroma, is described. The selenium dioxide oxidation of ethyl 1-methyl-2-oxocyclohexanecarboxylate (IIa) gave α-diketone (IIIa), which was then hydrolyzed and decarboxylated to afford Ia. The treatment of IIa with cupric chloride in 50% acetic acid also yielded Ia. The dimethyl sulfoxide oxidation of ethyl 3-bromo-1-methyl-2-oxocyclohexanecarboxylate (IV) afforded IIIa, along with 3-bromo-6-ethoxycarbonyl-2-hydroxy-6-methyl-2-cyclohexen-1-one (V). The halogenation of IIa produced dihalogeno ketoesters (VIa) (VIIa), which also yielded Ia in a pure state by means of a direct acidic hydrolysis or by a two-step hydrolysis using morpholine. Other allied compounds are also described.
  • Jitsuo Kiji, Satoshi Nishimura, Susumu Yoshikawa, Eiichi Sasakawa, Jun ...
    1974 Volume 47 Issue 10 Pages 2523-2525
    Published: 1974
    Released: March 27, 2006
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    The reactions of norbornadiene in amine by the use of nickel, palladium and rhodium complexes have been studied in the presence of protic acid. A catalytic system of Ni(COD)2 (1)-n-Bu3P gives a mixture of 5-exo-(o-tolyl)-2-norbornene (3) and 5-exo-(N-amino)-2-norbornene (4). Bis(triphenylphosphine)(maleic anhydride)palladium (5) gives 3-(N-amino)nortricyclene (6). Dichlorotetrakis(cyclooctene)dirhodium (10) gives a [2+4] cycloaddition product (11). All these reactions mechanisms are discussed from the point of view of an acid-promoted reaction on low-valent transition metal complexes.
  • Akira Kasahara, Taeko Izumi, Masatoshi Ooshima
    1974 Volume 47 Issue 10 Pages 2526-2528
    Published: 1974
    Released: March 27, 2006
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    The reaction of the sodium salt of 2′-hydroxychalcones with palladium(II) salt led to the formation of flavones, accompanied by a small amount of flavanones. The reaction proceeds via a phenoxypalladation, followed by the elimination of a hydridopalladium(II).
  • Hiroaki Taguchi, Katsuichi Shimoji, Hisashi Yamamoto, Hitosi Nozaki
    1974 Volume 47 Issue 10 Pages 2529-2531
    Published: 1974
    Released: March 27, 2006
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    The key step of the title synthesis involves the conversion of ethyl trimethylsilylacetate to the corresponding enolate, 1, by treatment with lithium dicyclohexylamide in tetrahydrofuran at −78 °C. The condensation of 1 with aldehydes and ketones proceeds smoothly to afford the desired two carbon homologated unsaturated esters in excellent yields. The new process is extended with success to readily-enolizable carbonyl compounds and also to chalcone, which gives no trace of the Michael adduct in the present reaction.
  • Kosaku Kishi, Shigero Ikeda
    1974 Volume 47 Issue 10 Pages 2532-2536
    Published: 1974
    Released: March 27, 2006
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    The reaction of the evaporated iron, nickel, and palladium with NO was investigated by X-ray photoelectron spectroscopy. On both iron and nickel larger part of NO dissociates to give two or more N(1s) and O(1s) photoelectron peaks which are ascribable to the surface oxide, nitride, and NO species. The proportion of these species is estimated roughly from the intensity ratios of the N(1s) and O(1s) peaks at 15 NO: 65 O: 20 N (iron) and 7 NO: 65 O: 28 N (nickel) when the metals are exposed to 5 Torr of NO gasfor 1 s, and 35 NO: 55 O: 10 N (iron) and 10 NO: 75 O: 15 N (nickel) when exposed to 10 Torr of NO for 10 min. On palladium the N(1s) for chemisorbed NO is observed. The N(1s) binding energies of the surface NO are compared with the N(1s) binding energies and the infrared NO frequencies of the corresponding transition metal nitrosyls.
  • Hiromu Sugeta, Yoshio Adachi, Tatsuo Miyazawa
    1974 Volume 47 Issue 10 Pages 2537-2544
    Published: 1974
    Released: March 27, 2006
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    Far infrared spectra were measured of ethyl fluoride CH3CH2F and deuterated species CH3CD2F, CD3CH2F, and CD3CD2F in the gaseous state. The potential barriers hindering the internal rotation were calculated with various models. Possibly because of isotope effects on structure relaxations due to torsional motion and to zeropoint motion of other vibrational modes, the observed potential barriers are slightly different among isotopic molecules; the threefold barrier is lowered on the deuteration of the methyl group. The absorption intensities of the four isotopic species were also measured. The intensity of the torsional vibration of the methyl group is nearly doubled on deuteration of the methyl group but is reduced on deuteration of the methylene group. The observed intensity ratios among isotopic species were in good agreement with the ratios calculated with the intensity theory of our previous study.
  • Kazutoshi Tanabe, Shinnosuke Saëki
    1974 Volume 47 Issue 10 Pages 2545-2548
    Published: 1974
    Released: March 27, 2006
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    Infrared absorption intensities of trans- and cis-dichloroethylene were measured in the vapor phase, and interpreted in terms of intensity parameters common to the isomers. In order to obtain L matrices, force constants common to the isomers were determined so as to attain the best fit between the observed and calculated frequencies of CHCl=CHCl, CDCl=CDCl and CHCl=CDCl. Using the L matrices thus obtained, intensity parameters were determined so as to attain the best fit between the observed and calculated intensities of CHCl=CHCl. As a result, the observed frequencies and intensities were satisfactorily represented in terms of the force constants and the intensity parameters common to the isomers.
  • Yoshihisa Suzuki
    1974 Volume 47 Issue 10 Pages 2549-2550
    Published: 1974
    Released: March 27, 2006
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    The solubilities of anhydrous inosine crystals in the α-form and in the β-form in water were determined in the temperature range between 20 °C and 60 °C. The results may be formulated as follows:
    & α-form & logS=0.0190 t-0.065
    & β-form & logS=0.0198 t-0.161
    These data indicate that the β-crystals are more stable than the α-crystals over the whole temperature range examined. However, the difference in solubility is too small to induce the transition without seed crystals in the β-form, so that the α-crystals themselves are practically stable in water. The rate of the transition from the α-form to the β-form varies in proportion to the amount of the seed β-crystals. At low temperatures the dihydrate form of inosine is more stable than both of these two anhydrous forms. The solubility may be formulated as follows:
    dihydrate-form logS=0.0314 t-0.276
  • Yoshihisa Suzuki, Kentaro Hara
    1974 Volume 47 Issue 10 Pages 2551-2552
    Published: 1974
    Released: March 27, 2006
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    The phase diagram for the inosine–dimethyl sulfoxide–water system was determined at 30 °C. Inosine in the α-form is more soluble than that in the β-form in aqueous DMSO. The difference in the solubilities between the two forms is small when the concentration of DMSO is below 50%. However, it becomes several times larger in 70% DMSO than in water. This is the reason why inosine in the β-form is often obtainable with ease from 70% DMSO in the absence of seed β-crystals, while it is with difficulty obtained only from water. When the concentration of DMSO becomes higher than 82%, a new solid phase is obtained. It consists of inosine with two mol of DMSO of crystallization. Inosine in the β-form is also obtainable with ease through the decomposition of these new crystals.
  • Yoshihisa Suzuki, Yasuichi Nomura
    1974 Volume 47 Issue 10 Pages 2553-2555
    Published: 1974
    Released: March 27, 2006
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    Solubility data have been obtained for the inosine–Ca(OH)2–H2O and inosine–Sr(OH)2–H2O systems at 10 °C. Three different solid phases of the calcium salt of inosine were found in the former system. The first is the normal hemi-calcium salt, (inosine) 2·Ca·2H2O; the second, an abnormal salt, (inosine)3·Ca·3H2O, and the third, another abnormal salt, (inosine)4·Ca·9H2O. The former two salts have stable regions in the system, while the last one does not. The system including Sr(OH)2 is simple, and no other salt-formation was found except for that of normal hemi-strontium salt, (inosine)2·Sr·2H2O. The X-ray powder diffraction data of the above four salts are given. The solubilities of the two normal hemi-alkaline-earth-metal salts of inosine in water were determined at 10—60 °C and formulated as follows:
    Ca-salt, logS & = 0.00406·t - 0.4725
    Sr-salt, logS & = 0.00551·t - 0.4116
    where S represents the gram weight of anhydrous salt per 100 g of water.
  • Yoshihisa Suzuki, Tadao Toki
    1974 Volume 47 Issue 10 Pages 2556-2558
    Published: 1974
    Released: March 27, 2006
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    Solubility data have been obtained for the inosine–NaOH–H2O and inosine–KOH–H2O systems at 30 °C. Two different solid phases of the potassium salt of inosine (C10H11N4O5·K·H2O and C10H11.5N4O5·0.5 K·0.5 H2O) were found in the latter system, while only one solid phase of the sodium salt of inosine (C10H11N4O5·Na·2.5 H2O) was found in the former system. The hemi-potassium salt of inosine is incongruent and is decomposed by pure water, whereas the mono-alkaline-metal salts are stable. The solubilities of the two mono-alkaline-metal salts of inosine in water were determined at 0–50 °C and formulated as follows:
    Na-salt, logS & = 0.01359·t+0.3997
    K-salt, logS & = 0.00733·t+1.6513
    where S represents the gram weight of the anhydrous salt per 100 g of water. The X-ray powder diffraction data of the above three salts are given.
  • Masahiro Imura, Hiroyasu Nomura, Fumio Kawaizumi, Yutaka Miyahara
    1974 Volume 47 Issue 10 Pages 2559-2562
    Published: 1974
    Released: March 27, 2006
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    The vapor-pressure depressions of solutions of four tetraalkylammonium halides in acetone were determined by means of a vapor-pressure osmometer. The experimental results were discussed by analyzing the relationship between the h(=1000lna1M1m+1) function and the concentration. The following conclusions are obtained: tetraalkylammonium salts are dissociated in acetone, and the thermodynamic behavior of the dissociated species is described by the Debye-Hückel-Onsager limiting formula with sufficient accuracy, where the undissociated species are assumed to behave ideally.
    Except for (n-Bu)4NCl, the dissociation constants determined by the present work are in good agreement with those found in the literature, which were determined conductometrically.
  • Tsunetoshi Kobayashi, Saburo Nagakura
    1974 Volume 47 Issue 10 Pages 2563-2572
    Published: 1974
    Released: March 27, 2006
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    Photoelectron spectra were measured in the region between 6 and 21 eV for aniline, N,N-dimethylaniline, phenol, anisole, benzonitrile, acetophenone, nitrobenzene, and their methyl derivatives. The observed spectra were interpreted in terms of their MO’s obtained by the CNDO/2 and EHMO methods, the methyl-substituent effect and the steric hindrance effect being considered. Both effects are essential for the reliable assignment of the observed photoelectron spectra. We found a general tendency that the interaction of the doubly degenerate highest occupied orbitals (e1g) of the benzene ring with the highest occupied orbital of a substituent group is important for the interpretation of the observed lower energy (7∼12 eV) bands. The only exceptional case is the nitrobenzenes in which the lowest vacant orbital of the substituent group is rather close to the highest occupied orbitals of the benzene ring and the interaction between them is important. The effects of the substituent groups upon the observed photoelectron spectra are classified into four types.
  • Takemasa Shibata, Tsutomu Fukuyama, Kozo Kuchitsu
    1974 Volume 47 Issue 10 Pages 2573-2575
    Published: 1974
    Released: March 27, 2006
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    Long-lived excited states of hydrogen, carbon and nitrogen atoms (H**, C** and N**) produced by the electron bombardment of CH3CN in the energy range from 20 to 100 eV were detected as H+, C+ and N+ ions as a result of collisions with H2O. The appearance potential of H+ was observed to be about 3 eV lower than the threshold energy for He+ formed from He** with H2O (about 24.6eV). The C+ threshold energy was about the same as that for He+, while that for N+ appeared to be a few eV higher. This suggests that the H** species is mainly responsible for the formation of CH3CN due to the electron bombardment of CH3CN observed by Sugiura and Arakawa, at least in the energy region below the He** threshold energy.
  • R. Abu-Eittah, M. M. Hamed
    1974 Volume 47 Issue 10 Pages 2576-2579
    Published: 1974
    Released: March 27, 2006
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    The electronic absorption spectra of some ketimines have been investigated using different solvents. Assignment of the obtained transitions was attempted. The N-substituted ketimines did not show a discrete band for the n–π* transition as was obtained with the unsubstituted molecules. Molecular orbital calculations were carried out using the PPP variant of the SCF-MO theory. Agreement between the calculated and experimental transition energies was satisfactory.
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