• Title/Summary/Keyword: azomethine group

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Electrochemical Behavior and Differential Pulse Polarographic Determination of Rifampicin in the Pharmaceutical Preparations

  • Hahn, Young-Hee;Shin, Sun-Mi
    • Archives of Pharmacal Research
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    • v.24 no.2
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    • pp.100-104
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    • 2001
  • Differential pulse polarographic(DPP) analytical procedure for the rifampicin antibiotic, which can be applied to monitor its synthetic process from the starting antibiotic of rifamycin B or rifamycin SV has been developed based on the electrochemical reduction of an azomethine group. Rifampicin exhibited a cathodic peak due to the azomethine group in the side chain of 3-[(4-methyl-1-piperazinyl)imino]methyl moiety and another cathodic peak due to the carbonyl group in rifamycin SV by DPP. The experimental peak potential shift of an azomethine reduction was -73 mV/pH in the pH range between 3.0 and 7.5, agreeing with involvement of 4 e-and 5 $H^5$ in its reduction. By the cyclic voltammetric(CV) studies, the azomethine and the carbonyl reductions in rifampicin were processed irreversibly on the mercury electrode. The plot of peak currents vs. concentrations of rifampicin ranging $1.0{\times}10^{-7} M~$1.0{\times}10^{-5} M yielded a straight line with a correlation coefficient of 0.9996. The detection limit was $1.0{\times}10^{-8} M with a modulation amplitude of 50 mV DPP has been successfully applied for the determination of rifampicin in the pharmaceutical preparations.

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Dipole-Forming Photochemical Group Transfer Reactions of Phthalimides and ${\alpha}-Ketoamides$

  • Yoon, Ung-Chan;Mariano Patrick S.
    • Journal of Photoscience
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    • v.12 no.3
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    • pp.155-162
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    • 2005
  • Results of studies of SET-promoted dipole-forming photochemical group transfer reactions of phthalimide and ${\alpha}-ketoamide$ derivatives are discussed. Azomethine ylide forming photochemical reactions, which are initiated by intramolecular SET from tethered silylmethyl-, carboxymethyl-, and ${\beta}-hydroxyethyl$ containing electron donors to excited states of phthalimides, related maleimides, and conjugated imides, are presented first. Following this, investigations of regioselective 1,4-dipole forming photochemical reactions of N-trialkylsilylmethyl- and N-trialkylstannyl-${\alpha}$-ketoamides are described.

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Synthesis of Conjugated Copolymers with phenothiazine and Azomethine Units and their Electro-Optic Properties

  • Seo, Hyeon-Jin;Jang, Byeung-Jo;Chang, Jin-Gyu;Park, Lee-Soon
    • Journal of Information Display
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    • v.2 no.4
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    • pp.8-14
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    • 2001
  • Three types of conjugated polymers, poly(PZ-Pi), poly(PZ-BPI) and poly(PZ-NPI) were synthesized by Schiff-base reaction. These new conjugated polymers exhibited improved solubility in common organic solvents due to the presence of alkyl side chains as well as azomethine groups, Double layer LEDs made with the synthesized polymers as emitting layer and $Alq_3$, as electron transporting layer exhibited enhanced EL emission and efficiency compared to those of single layer LEDs. Double layer LEDs exhibited gradual shift in the emission peak th the single layer LED, made of only $Alq_3$ as the emitting layer as the thickness of $Alq_3$ layer increased.

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Synthesis of Poly(enaryloxynitriles) Containing Schiff Bases and Their Thermal Properties

  • 김상곤;한양규;공명선
    • Bulletin of the Korean Chemical Society
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    • v.16 no.4
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    • pp.326-331
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    • 1995
  • Poly(enaryloxynitriles) containing Schiff bases were prepared from p-bis(1-chloro-2,2-dicyanovinyl)benzene (2) and various aromatic diols having Schiff base moiety by interfacial polymerization. The chemical structure of the polymers was confirmed through synthesis of their corresponding model compounds. All the polymers were soluble in polar aprotic solvents and their brittle films were cast from DMF solution. They showed a large exotherm around 340 ℃ attributable to the chemical change of dicyanovinyl group. Especially, curing of azomethine group was observed to occur at 390 ℃ by differential scanning calorimetry. According to the thermogravimetric analyses, they exhibited excellent thermal stability with 60-90% residual weight at 500 ℃ in nitrogen.

Mechanism of the Hydrolysis of Phenyl N-(p-chlorobenzoyl)Chloroformimidate Derivatives in Acid Media (산성용액 중에서 Phenyl N-(p-chlorobenzoyl)chloroformimidate 유도체의 가수분해 반응 메카니즘)

  • Nack-Do Sung;Young-Gu Cheun;Ki-Sung Kwon;Tae-Rin Kim
    • Journal of the Korean Chemical Society
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    • v.31 no.4
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    • pp.352-358
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    • 1987
  • Rate constants for the hydrolysis of para-substituted phenyl N-(p-chlorobenzoyl)chloroformimidate (I) derivatives in 1 : 4 dioxane-water at $25^{\circ}C$ have been determined. Rate data, substituent effect $(\rho\>{\rho}^+)$, product analysis and MO calculation indicate that the uncatalyzed reaction proceeds through an $S_N1$ mechanism involving the formation of azocarbonium ion (II) below pH 3.0, and the base-catalyzed reaction proceeds through an $S_N2$ mechanism via transition state (III) above pH 4.0. The relative stability of four peri planar conformational isomers were (E-ap) > (Z-ap) > (E-sp) > (Z-ap), respectively, and the most stable stereo structures shows that the Y-substituted phenyl group $(C_6H_4-Y)$ occupy vertical $(90^{\circ})$ position on the plane of the benzimidochloroformyl group in (E-ap) conformer. The nucleophilic substitution of water molecule occurs by sigma attack to the activatived azomethine carbon atom of (I) derivatives.

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Investigation of Diazepam by Pulsed Rotation Voltammetry

  • Blaedel, W.J.;Hahn, Young-Hee
    • Archives of Pharmacal Research
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    • v.2 no.2
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    • pp.111-114
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    • 1979
  • Diazepam was investigated in aqueous buffer media using pulsed rotation voltammetry. The dependence of half-wave potentials on pH indicated a two proton involvement in a two electron transfer reduction in the pH range 3-10. Dizaepam at micromolar concentration levels may be determined by measurement of the limiting difference current.

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Kinetics and Mechanism of the Hydrolysis of N-Arylsulfonylbenzimidothiophenyl ester (N-Arylsulfonylbenzimidothiophenyl Ester 유도체의 가수분해에 대한 반응속도론적 연구)

  • Tae-Seong Huh;Tae-Rin Kim
    • Journal of the Korean Chemical Society
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    • v.20 no.1
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    • pp.73-86
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    • 1976
  • Four unreported derivatives of N-arylsulfonylbenzamide and six derivatives of N-arylsulfonylbenzimidothiophenyl ester were prepared. These were; p-methyl-N-(arylsulfonyl)benzamide, m-methyl-N-(arylsulfonyl)benzamide, m-nitro-N-(arylsulfonyl)benzamide, p-methoxy-N-(arylsulfonyl)benzamide, p-methyl-N-(arylsulfonyl)benzimidothiophenyl esters, p-chloro-N-(arylsulfonyl)benzimidothiophenyl ester, m-methyl-N-(arylsulfonyl)benzimidothiophenyl ester, p-nitro-N-(arylsulfonyl)benzimidothiophenyl ester, m-nitro-(arylsulfonyl)benzimidothiophenyl ester and p-methoxy-N-(arylsulfonyl)benzimidothiophenyl ester. The rate constants of the hydrolysis of N-arylsulfonylbenzimidothiophenyl esters were determined by ultraviolet spectrophotometry at various pH and rate equations which can be applied over a wide pH range were obtained. From the rate equation and substituent effects, one can conclude that above pH 11, the hydrolysis of N-arylsulfonylbenzimidothiophenyl esters are initiated by the attack of hydroxide ion, however, below pH 9, started by the addition of a water molecule on the azomethine group. At pH 9∼11, the competitive reaction between a water molecule and hydroxide ion is anticipated to occur.

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Structure activity relationships on the herbicidal activities of 5-(2,3-dihydro-2,2-dimethylbenzothiophene-7-yl)-2-(1-(alkoxyimino)butyl)-3-hydroxy-2-cyclohexene-1-one derivatives (5-(2,3-dihydro-2,2-dimethylbenzothiophene-7-yl)-2-(1-(alkoxyimino)butyl)-3-hydroxy-2-cyclohexene-1-one 유도체의 구조와 살초활성 관계)

  • Sung, Nack-Do;Song, Jong-Whan
    • The Korean Journal of Pesticide Science
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    • v.4 no.2
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    • pp.69-71
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    • 2000
  • The herbicidal activities ($pI_{50}$) with alkoxy (RO-) groups on the azomethine nitrogen atom in 5-(2,3-dihydro-2,2-dimethylbenzothiophene-7-yl)-2-(1-(alkoxyimino)butyl)-3-hydroxy-2-cyclohexene-1-one derivatives against various weeds were measured in the flooded and in the paddy conditions. Particularly, i-propoxy subsutuent, 5 of them showed excellent herbicidal activity at a rate of 4kg/ha with pre-emergence against barnyard grass (Echinochloa crus-galli) with good selectivity on rice plant (Oryza sativa). The results of the structure-activity relationships (SAR) analyses are shown that the alkyl subsituents with higher hydrophobicity (logp>0) and electron donating (${\sigma}^*<0$) group as a new substrate rather than alkoxy substituents seems to be contribute to the herbicidal activity with pre-emergence.

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1,2,4-Triazole Fused Heterocycles; Part 3. Preparation of 1-(1-Phenylethenyl)-5-(N-substituted amino)-1,2,4-triazoles and 4H-1,2,4-Triazolo[1,5-c][1,3,5]oxadiazines

  • 이기정;이유석;송동혁
    • Bulletin of the Korean Chemical Society
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    • v.16 no.11
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    • pp.1037-1042
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    • 1995
  • The reaction of acetophenone 1-ureidoethylidenehydrazones 6 with a mixture of triphenylphosphine, carbon tetrachloride, and triethylamine in dichloromethane provides a general route to 1-(1-phenylethenyl)-5-(N-substituted amino)-1,2,4-triazoles 11 via the electrocyclization of the expected azino carbodiimide intermediates 9 to give the resonance stabilized azomethine imine 10a followed by a proton abstraction from the methyl group by amide anion. However, the same reaction of benzaldehyde 1-ureidoethylidenehydrazones 5 was unsuccessful. Under the same conditions, the reactions of benzaldehyde 1-N-acylureidoethylidenehydrazones 7 or acetophenone 1-N-acylureidoethylidenehydrazones 8 afforded 4H-1,2,4-triazolo[1,5-c][1,3,5]oxadiazines 16 or 17 via the zwitterionic species 15, or a [4+2] intramolecular cycloaddition from the carbodiimide intermediates 14, respectively.

Preparation and Thermal Properties of Enaryloxynitriles End-Capped Polymer Precursors

  • Gil, Dae Su;Gong, Myeong Seon
    • Bulletin of the Korean Chemical Society
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    • v.21 no.6
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    • pp.557-561
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    • 2000
  • Various enaryloxynitriles-terminated reactive polymer precursors containing rigid aromatic units were prepared from various diamines and 1-(p-formylphenyl)-1-phenyl-2,2-dicyanoethene (1). Arylate end-capped model compounds linked with azomethine bond were also prepared by reacting p-formylphenyl benzoate with diamines to compare the curing ability. The oligomers were highly soluble in polar aprotic solvents such as N,N-dimethylformamide, dimethylsulfoxide and N-methyl-2 -pyrrolidinone. They generally showed an exothermic curing process between $280-350^{\circ}C$, attributable to the thermal crosslinking of the dicyanovinyl group in DSC analysis, and no weight loss at curing temperature. Upon heating the polymer precursors, heat-resistant and insoluble network polymers were obtained. Thermogravimetric analyses of the precursors containing rigid aromatic units showed thermal stability with a 77-92% residual weight at $500^{\circ}C$ under nitrogen.