Bulletin of the Chemical Society of Japan - Vol. 78, No. 12 (December, 2005)

Bulletin of the Chemical Society of Japan
Vol. 78, No. 12 (December, 2005)

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Award Accounts

The Chemical Society of Japan Award for Young Chemists for 2004

Web Release Date: December 9, 2005

2083-2097 Synthesis of Highly Functional Nucleic Acids and Their Application to DNA Technology
A. Okamoto
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Several highly functional nucleic acids have been synthesized and applied to DNA technology. Synthetic functional bases have been spatially arranged in the DNA structure, and the various functions of these DNAs have been modulated by changes in their sequences and microenvironments.

Web Release Date: December 9, 2005

2098-2104 Multi-pH Monte Carlo Simulation of Coil–Globule Transition of Weak Polyelectrolyte
T. Yamaguchi,^* T. Kiuchi, T. Matsuoka, and S. Koda^*
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A multi-pH generalized ensemble simulation method is proposed; it is applied to the titration of the model weak polyelectrolyte. The first-order coil–globule transition is found in a poor solvent case. The conformation of the transition state is closely examined.

Web Release Date: December 9, 2005

2105-2113 Molecular-Dynamics Simulation of a Methane–Oxygen Mixture: Prediction of P–V–T Data and Evaluation of Effective Pair Potential Models
N. Seyed Matin^* and A. H. Jalili
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The results of molecular-dynamics simulation using various isotropic pair potential functions for pure methane, oxygen, and their binary mixtures in the temperature range of 200 to 600 K and densities up to about 1.5 times their critical density is presented. Considering the predicting capability of mentioned potential functions for pure methane and oxygen, two of them were selected for investigation of methane–oxygen binary mixtures.

Web Release Date: December 9, 2005

2114-2123 Paramagnetic Semiconductors: Hybrid Molecular Materials Based on Ethyl- and Methyl-pyridinium-Substituted Verdazyl Radical Cations and the Ni(dmit)₂ Anion (dmit = 1,3-Dithiol-2-thione-4,5-dithiolate)
K. Mukai,^* D. Shiba, K. Yoshida, K. Mukai, H. Hisatou, K. Ohara, Y. Hosokoshi, and N. Azuma
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Four kinds of 1:1 salts of 3-(3- and 4-alkyl-pyridinium)-1,5-diphenylverdazyl (alkyl = ethyl and methyl) radical cations with the Ni(dmit)₂ anion have been found to be new paramagnetic semiconductors.

Web Release Date: December 9, 2005

2124-2129 Theoretical Study on the Disproportionation Reaction of Nickel(II) Mixed-Ligand Complexes Containing N,N,N′,N′-Tetramethylethylenediamine, Benzoylacetonate, and a Halide Anion
K. Miyamoto, K. Takano,^* and Y. Fukuda^*
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DFT calculations were performed on a disproportionation reaction exhibited by Ni(II) mixed-ligand complexes. Two isomers of the intermediate 5-coordinate complex, having nearly the same thermodynamic stabilities, isomerize between square-pyramidal and trigonal-bipyramidal geometries via a TS structure.

Web Release Date: December 9, 2005

2130-2134 Detection of Hidden Mercury in Cosmetic Products by Partially Cross-Linked Poly(4-vinylpyridine)/Screen-Printed Electrode
Y. Shih,^* A. Senthil Kumar, J.-M. Zen,^* and J.-C. Hsu
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Disposable screen-printed electrode partially cross-linked with poly(4-vinylpyridine) (SPE/pcPVP) modified system has been demonstrated for the detection of the hidden toxic [Hg] as [HgCl₄]²⁻ form in skin-lightening cosmetics goods.

Web Release Date: December 9, 2005

2135-2141 Application of Supported Liquid Membranes in the Multi-Residue Extraction of Aminoglycoside Antibiotics in Milk and Urine
T. A. M. Msagati^* and M. M. Nindi
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This manuscript reports on the method development for the extraction of aminoglycosides from milk and urine matrices. A supported liquid membrane has been used as an enrichment technique. The separation and detection of the analytes was performed using LC-ESI-SIM-MS.

Web Release Date: December 9, 2005

2142-2145 Properties of Acid Sites Generated on Sol–Gel Derived Zn₂SiO₄
H. Nakabayashi,^* Y. Shino, and J. Kobayashi
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High catalytic activity and large amounts of strong acid sites were observed on sol–gel derived Zn₂SiO₄, which was just formed by the reaction between ZnO and SiO₂ particles at 1173 K.

Web Release Date: December 9, 2005

2146-2151 Steric Effect of 3,5-Bis(trifluoromethyl)phenol as Hydrogen-Bond Donor on Outer-Sphere Complexation in the Synergistic Extraction of Aluminium(III) and Gallium(III) with 2,4-Pentanedione
H. Imura,^* T. Namai, K.-i. Ishimori, S. Hayashi, A. Ohashi, and K. Ohashi
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A large enhancement of the extraction of metal(III) was ascribed to the formation of outer-sphere complexes through hydrogen bonds between metal(III) chelates and BTMP in heptane. The bulky trifluoromethyl-group caused a steric hindrance, which improved the separation of metals(III).

Web Release Date: December 9, 2005

2152-2158 Synthesis and Characterization of Ruthenium(II)–Nitrile Complexes with Bisamide-tpa Ligands (tpa = Tris(2-pyridylmethyl)amine)
T. Kojima,^* K.-i. Hayashi, Y. Shiota, Y. Tachi, Y. Naruta, T. Suzuki, K. Uezu, and K. Yoshizawa
[Full Text PDF(J-STAGE)] [Supporting Information]

Ru(II)–acetonitrile complexes of tris(2-pyridylmethyl)amine with aromatic and aliphatic amide groups were prepared and characterized by various spectroscopic methods, electrochemical measurements, and DFT calculations. Those complexes exhibited a fluxional thermal motion in solutions.

Web Release Date: December 9, 2005

2159-2160 Preparation and Structure of syn- and anti-Bis(μ-thioacetato-κ²S)bis[bis(dithioacetato-κS:κS′)iridium(III)]
M. Ebihara,^* N. Kanematsu, M. Yoshida, and T. Kawamura
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Iridium(III) dinuclear complexes with thioacetato bridges and dithioacetato chelates were prepared by the reaction of H₂IrCl₆·6H₂O with a mixture of Li₂CO₃, MeCOSH, MeCO₂H, and (MeCO)₂O under O₂. X-ray structures of two geometrical isomers for [{Ir(S₂CMe)₂}₂(μ-SOCMe)₂] were determined.

Web Release Date: December 9, 2005

2161-2163 Chiral Distortion of Di(μ-sulfido)bis[oxomolybdenum(V)] Complexes of a Hexadentate Ligand N,N,N′,N′-Tetrakis(2-pyridylmethyl)-R-propylenediamine and Its Analogs
H.-Y. Jin, R. Hazama, M. Yamasaki, K. Umakoshi,^* K. Tsuge, and Y. Sasaki^*
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Chiral distortion of the basal four pyridyl nitrogen donors of the titled complex [Mo₂(O)₂(μ-S)₂(μ-N,N,N′,N′-tetrakis(2-pyridylmethyl)-R-propylenediamine)]²⁺ has been found to be the reverse to that of the corresponding di-μ-oxo complex, on the basis of the inverse pattern of the circular dichroism spectra.

Web Release Date: December 9, 2005

2164-2170 Electronic Properties and Thermal Stability of Soluble Redox Proteins from a Thermophilic Purple Sulfur Photosynthetic Bacterium, Thermochromatium tepidum
M. Kobayashi,^* T. Saito, K. Takahashi, Z.-Y. Wang, and T. Nozawa
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Four soluble redox proteins have been isolated from T. tepidum and characterized. A new cytochrome c-552 with a lower potential (−15 mV) was found for the first time in T. tepidum. The midpoint redox potentials as well as electron-transfer experiments suggest that HiPIP is the possible electron carrier protein for the RC. The thermal stability of the protein also supports this conclusion.

Web Release Date: December 9, 2005

2171-2174 Synthesis of 11H-Indolo[3,2-c]quinoline Derivatives Carrying a Substituent at the 6-Position
K. Kobayashi,^* Y. Izumi, K. Hayashi, O. Morikawa, and H. Konishi
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The treatment of 2-(2-isocyanophenyl)-1-methyl-1H-indole with aldehydes, ketones, acetals (=E) (in the presence of a catalytic amount of a Lewis acid), or N,N-dimethyliminium salts afforded 6-(1-hydroxy- or alkoxyalkyl)- or 6-(1-dimethylaminoalkyl)-11H-indolo[3,2-c]quinolines in satisfactory yields.

Web Release Date: December 9, 2005

2175-2179 Synthesis of a Molecular Tweezer Containing Pentafluorophenyl Groups and Investigation of the π–π Stacking Interaction for a Pentafluorophenyl Group in a Polar Organic Solvent
T. Korenaga,^* Y. Kawauchi, T. Kosaki, T. Ema, and T. Sakai^*
[Full Text PDF(J-STAGE)] [Supporting Information]

A molecular tweezer having two bidentate pentafluorophenyl (C₆F₅) groups was synthesized, and the π–π stacking ability of the C₆F₅ group toward benzene derivatives in a polar organic solvent was evaluated.

Web Release Date: December 9, 2005

2180-2187 An Azacrowned Phthalimide as a Metal-Ion Sensitive and Solvatofluorochromic Fluorophore: Fluorescence Properties and a Mimic Integrated Logic Operation
H. Okamoto,^* M. Kohno, K. Satake, and M. Kimura
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A novel azacrowned phthalimide has been prepared and its fluorescence properties were studied. Color alternation and switching of the fluorescence of the phthalimide were achieved by addition of EtOH and Ag⁺, respectively. The potential logic operation was described.

Web Release Date: December 9, 2005

2188-2208 Nickel-Catalyzed Dimerization of [5]Cumulenes (Hexapentaenes)
Y. Kuwatani, G. Yamamoto, M. Oda, and M. Iyoda^*
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[5]Cumulenes (hexapentaenes) react with low-valent nickel complex at the second double bond to afford novel [4]radialene derivatives. Furthermore, the nickel-catalyzed dimerization of [5]cumulenes with bulky substituents produces [5]radialenones. The unique structures and interesting properties of [5]cumulene dimers are reported.

Web Release Date: December 9, 2005

2209-2213 Synthesis of Cyclic Ethers from 3- and 4-Hydroxyalkylphosphonium Salts
K. Okuma,^* O. Sakai, T. Hayano, K. Shioji, and H. Matsuyama
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The reaction of 6-methylene-1,3-dioxepanes derived from 3-hydroxyalkyltriphenylphosphonium salts and paraformaldehyde with trimethylsilyl trifluoromethanesulfonate in the presence of N,N-diisopropylethylamine yielded novel 4-formyltetrahydropyrans. 3-Methylenetetrahydropyrans were synthesized by the reaction of 4-hydroxyalkyltriphenylphosphonium iodides with DBU and paraformaldehyde.

Web Release Date: December 9, 2005

2214-2227 Chemistry of Anthracene–Acetylene Oligomers. II. Synthesis, Structure, and Properties of 1,8-Anthrylene–Ethynylene Cyclic Tetramers and Related Acyclic Oligomers
S. Toyota,^* M. Goichi, M. Kotani, and M. Takezaki
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The title π-conjugated oligomers were synthesized by Sonogashira coupling. The cyclic tetramer takes a diamond prism structure as revealed by X-ray analysis, and undergoes skeletal swing between two enantiomeric forms with a barrier of ca. 38 kJ mol⁻¹. The structural and spectral properties of the cyclic tetramer and the related acyclic oligomers are presented.

Web Release Date: December 9, 2005

2228-2234 Enantiomeric Resolution and Absolute Stereochemistry of Stable Rotamers of Dimethyl 6,6′-Dimethyl-9,9′-bitriptycyl-2,2′-dicarboxylate as a Stereochemical Analog of (R*,R*)- and (R,S)-Tartaric Acids
S. Toyota,^* A. Takau, Y. Hitaka, M. Ōki, and K. Wakamatsu
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Two rotamers of the (R*,R*) form of the title compound were isolated, and their stereochemistries were determined by X-ray analysis. The enantiomers of each rotamer were resolved by chiral HPLC. The absolute stereochemistry was predicted by the TDDFT method.

Web Release Date: December 9, 2005

2235-2237 Electrophilic Arylation of Phenols: Construction of a New Family of 1-Methyl-2-quinolones
M. Asahara, M. Ohtsutsumi, M. Tamura, N. Nishiwaki,^* and M. Ariga^*
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1-Methyl-3,6,8-trinitro-2-quinolone readily reacted with phenoxides to cause electrophilic arylation leading to (1,2-dihydro-4-quinolyl)phenols which constitute a new family of 1-methyl-2-quinolones.

Web Release Date: December 9, 2005

2238-2244 Synthesis, Characterization, and Catalytic Performance of a ZSM-5/Y Composite
B. Shen,^* H. Chen, J. Guo, and H. Pan
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A ZSM-5/Y composite zeolite was prepared from Y synthesis gel by using an in-situ two-step hydrothermal crystallization process. Optimized synthetic parameters made it practical to control the transformation of zeolite Y to P, or other undesired phases during ZSM-5/Y composite formation. A heavy oil catalytic cracking reaction suggested that the ZSM-5 and Y zeolite in the composite exhibited a synergy effect.

Web Release Date: December 9, 2005

2245-2250 Employment of ³¹P MAS NMR for the Identification of Amorphous Precipitation Products Obtained from the MAP Process
S. Sugiyama,^* M. Fujisawa, M. Yokoyama, K.-i. Sotowa, T. Tomida, and N. Shigemoto
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Solid-state ³¹P MAS NMR revealed that solids recovered after the immobilization of aqueous PO₄³⁻ and NH₄⁺ with MgO and MgCl₂ contained various phosphates together with MAP, even though single MAP phase was detected from the solids by X-ray diffraction.

Web Release Date: December 9, 2005

2251-2258 Effects of Axial Ligands on the Formation of a Layered Structure in Mono- and Di-Cationic Charged Tetraphenylporphyrinatoantimony(V)/Synthetic Clay Composites
T. Shiragami,^* K. Nabeshima, S. Nakashima, J. Matsumoto, S. Takagi, H. Inoue, and M. Yasuda
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Metalloporphyrin–clay composites were prepared from a synthetic clay (SSA) and cationic tetraphenylporphyrinatoantimony(V) (SbTPP) complexes. Both the crystal structure for their composites and the adsorption behavior of SbTPP into SSA sheets were investigated concerning the relation to an axial ligand structure at SbTPP.