• Title/Summary/Keyword: Carboxylic Acids

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Reaction of Lithium Cyanoaluminum Hydride with Selected Organic Compounds Containing Representative Functional Groups. Comparison of Reducing Characteristics between Lithium and Sodium Cyanoaluminum Hydrides

  • Cha, Jin-Soon;Yu, Se-Jin
    • Bulletin of the Korean Chemical Society
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    • v.30 no.7
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    • pp.1588-1592
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    • 2009
  • Lithium cyanoaluminum hydride (LCAH) was prepared by the metal cation exchange reaction of sodium cyanoaluminum hydride with lithium chloride in tetrahydrofuran. The reducing characteristics of LCAH were explored systematically by the reaction with selected organic compounds containing representative functional groups under the standardized conditions (tetrahydrofuran, 0 ${^{\circ}C}$). The reducing ability of LCAH was also compared with of the sodium derivative, sodium cyanoaluminum hydride (SCAH). Generally, the reducing behavior of LCAH resembles that of SCAH closely, but the reactivity of LCAH toward representative organic functional groups appeared to be stronger than that of SCAH. Thus, the regent reduces carbonyl compounds, epoxides, amides, nitriles, disulfides, carboxylic acids and their acyl derivatives to the corresponding alcohols or amines, at a relatively faster rate than that of SCAH. The cyano substitution, a strong election-withdrawing group, diminishes the reducing power of the parent metal aluminum hydrides and hence effects the alteration of their reducing characteristics.

Design, Synthesis and Antibacterial Activity Studies of Novel Quinoline Carboxamide Derivatives

  • Shivaraj, Yellappa;Naveen, Malenahalli H.;Vijayakumar, Giriyapura R.;Kumar, Doyijode B. Aruna
    • Journal of the Korean Chemical Society
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    • v.57 no.2
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    • pp.241-245
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    • 2013
  • A series of novel quinoline-6-carboxamides and 2-chloroquinoline-4-carboxamides were synthesized by the reaction of their analogous carboxylic acids with various amine derivatives in the presence of base TEA and protecting agent BOP at room temperature. Synthesized compounds were confirmed by spectral characterization viz IR, $^1H$-NMR, and MS. Antibacterial activity carried out against Escherichia coli and Staphyllococcus aureus indicated that the synthesized compounds were active against these microorganisms.

Analysis of Phenolic Components in Korean Red Ginseng by GC/MS (홍삼 페놀성 성분의 GC/MS분석)

  • Wee, Jae-Joon;Heo, Jeong-Nam;Kim, Man-Wook
    • Journal of Ginseng Research
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    • v.20 no.3
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    • pp.284-290
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    • 1996
  • To Identify phenolic components known to exist in Korean ginseng (Panax ginseng C.A. Meyer) by GC/MS, three derivatization methods were employed for their analyses. First, phenolic components in ether soluble acidic fraction prepared from Korean red ginseng powder were taimethylsilylated. Secondly, phenolic acids in the same fraction were esterified with diazomethane followed by trlmethylsilylation. Thirdly, acidic components in ginseng powder were extracted and esterified concurrently by methanolic sulfuric acid, followed by fractionation of phenolic components with Silica Sep-Paka and trimethylsilylatlon. All phenolic components found in ginseng except gen tisic acid were identified by retention times and mass spectrums of standards. Besides, 5 phenolic components including salicyl alcohol and 1-H-indole-2-carboxylic acid were first identified from Korea an red ginseng by GC/MS.

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Synthesis and Lubrication Properties of Semi-Fluorinated Polyol Esters (불소계 폴리올에스테르의 합성과 윤활 특성)

  • 백진욱;정근우;김영운
    • Proceedings of the Korean Society of Tribologists and Lubrication Engineers Conference
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    • 2001.06a
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    • pp.149-155
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    • 2001
  • New semi-fluorinated polyol esters were synthesized by condensation reaction of polyols (NPG and TMP) and carboxylic acids such as 2-ethylhexanoic acid, stearic acid and perfluorooctanoic acid. The structures of polyol esters were confirmed by FT-IR and H-NMR etc. And, the fluorinated polyol esters were insoluble in several oils, however, the semi-fluorinated polyol esters were soluble in several oils depended on the structure of polyol esters. The physical properties such as 4-ball wear property and extreme-pressure (EP) properties were characterized by measuring wear scar diameter through ASTM D2266 and by determining the load-carrying through ASTM D2783 method, respectively. As the results, wear scar diameters of oils in which the semi-fluorinated polyol esters were added were not changed compared to those of not added oils. While extreme-pressure properties remarkably Increased with fluorine contents of the esters depended on the structure of acid moiety and polyol moiety. Also, the extreme-pressure property of semi-fluorinated NPG polyol ester in gasoline engine oil was better than that of commercial Teflon coating additive.

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Selective Reduction by Lithium Bis- or Tris(dialkylamino)aluminum Hydrides. Ⅶ. Reaction of Lithium Tris(dihexylamino)aluminum Hydride with Selected Organic Compounds Containing Representative Functional Groups$^1$

  • Cha, Jin-Soon;Kwon, Oh-Oun;Lee, Jae-Cheol
    • Bulletin of the Korean Chemical Society
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    • v.14 no.6
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    • pp.743-749
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    • 1993
  • The approximate rates and stoichiometry of the reaction of excess lithium tris(dihexylamino)aluminum hydride(LTDHA) with selected organic compounds containing representative functional groups under the standardized conditions (tetrahydrofuran, 0$^{\circ}$C) were studied in order to define the reducing characteristics of the reagent for selective reductions. The reducing ability of LTDHA was also compared with those of the parent lithium aluminum hydride(LAH), lithium tris(diethylamino)aluminum hydride(LTDEA), and lithium tris(dibutylamino)aluminum hydride(LTDBA). In general, the reactivity toward organic functionalities is in order of $LAH{\gg}LTDEA{\geq}LTDBA>LTDHA$. LTDHA shows a unique reducing characteristics. Thus, the reagent reduces aldehydes, ketones, esters, epoxides, and tertiary amides readily. Anthraquinone is cleanly reduced to 9,10-dihydro-9,10-anthracenediol without hydrogen evolution, whereas p-benzoquinone in inert to LTDHA. In addition to that, disulfides are also readily reduced to thiols without hydrogen evolution. However, carboxylic acids, anhydrides, nitriles, and primary amides are reduced slowly. Especially, this reagent reduces aromatic nitriles to the corresponding aldehydes in good yields.

Cupric Complexes Produced from the Reaction of Cupric Nitrate Trihydrate with S-2-Pyridyl Thioates

  • Choi, Young-Nam;So, Hyun-Soo;Lee, Jae-In;Kim, Sung-Gak
    • Bulletin of the Korean Chemical Society
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    • v.7 no.5
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    • pp.385-388
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    • 1986
  • The reaction of cupric nitrate trihydrate with S-2-pyridyl thioates in acetonitrile was studied. The major products were the corresponding carboxylic acids and $[Cu(NO_3)(C_5H_4NS)(C_5H_5NS$)] (Complex A). Sometimes $[Cu(NO_3)(C_5H_4NS)(H_2O$)] was also obtained in addition to Complex A. When Complex A was recrystallized in dimethylsulfoxide, $[Cu(NO_3)(C_5H_4NS)(C_5H_5NS)$ {$(CH_3)_2SO$}$_2]{\cdot}2H_2O$ was crystallized. The structures of these copper complexes and the role of cupric nitrate in the hydrolysis of S-2-pyridyl thioates are discussed.

Benzotriazol-1-yl Diethyl Phosphate and Benzotriazol-1-yl Diphenyl Phosphate. New Convenient Reagents for the Peptide Synthesis

  • Kim, Sung-Gak;Chang, He-Ung;Ko, Young-Kwan
    • Bulletin of the Korean Chemical Society
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    • v.8 no.6
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    • pp.471-475
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    • 1987
  • Benzotriazol-1-yl Diethyl phosphate and benzotriazol-1-yl diphenyl phosphate were conveniently prepared in essentially quantitative yields by the reaction of diethyl chlorophosphate and diphenyl chlorophosphate with equal amounts of 1-hydroxybenzotriazole and triethylamine in tetrahydrofuran at room temperature, respectively. Benzotriazol-1-yl diethylphosphate was effective for the preparation of amides from carboxylic acids amines. Young test and Anderson test for racemization studies using benzotriazol-1-yl diethyl phosphate were investigated and practically no racemization occurred. However, racemization occurred to some extent during coupling of Z-Phe-Val-OH with Pro-OBu. Several dipeptides and tripeptides were prepared without little racemization using benzotriazol-1-yl diethyl phosphate. Benzotriazol-1-yl diphenyl phosphate was less effective than benzotriazol-1-yl diethyl phosphate in terms of the degree of racemization.

Substituent Effects on the Reactivity of the Pyridines$^{1,2}$

  • 정덕영;권정민;여수동;박성식;이오석
    • Bulletin of the Korean Chemical Society
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    • v.16 no.7
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    • pp.604-609
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    • 1995
  • The relative dissociation constants of 4-substituted bicyclo[2,2,2]octane-1-carboxylic acids, 4-substituted quinuclidines, and 3-and 4-substituted pyridines were collected from a number of sources. In order to understand the actual substituent effects with a combination of inductive effect (σI) and resonance effect (σR) components. The DSP correlation has been employed statistically for each of the p-and m-series. The inductive effect from the m-position was 1.2 times more effective than that from the p-position and the requirement of σR+ for the best-fit led to the conclusion that pyridine system belongs to the σ+-class reactivity. Also compared with results from Yukawa-Tsuno's LArSR treatment and relevant treatment.

Reaction of 2,2'-Biphenoxyborane in Tetrahydrofuran with Selected Organic Compounds Containing Representative Functional Groups

  • Cha, Jin-Soon;Kim, Jong-Mi;Lee, Ja-Cheol;Lee, Hyung-Soo
    • Bulletin of the Korean Chemical Society
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    • v.12 no.6
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    • pp.612-617
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    • 1991
  • The approximate rates and stoichiometry of the reaction of excess 1,3,2-biphenyldioxaborepin [2,2'-biphenoxyborane (BPB)] with selected organic compounds containing representative functional groups under the standardized conditions (tetrahydrofuran, hydride to compound being 4 : 1, room temperature) was examined in order to define the characteristics of the reagent for selective reductions and compare its reducing power with those of other substituted boranes. The results indicate that BPB is unique and the reducing power is much stronger than that of other dialkoxyboranes, such as catecholborane and di-s-butoxyborane. BPB reduces aldehydes, ketones, quinones, lactones, tertiary amides, and sulfoxides readily. Carboxylic acids, anhydrides, esters, and nitriles are also reduced slowly. However, the reactions of acid chlorides, epoxides, primary amides, nitro compounds, and disulfides with this reagent proceed only sluggishly.