• Title/Summary/Keyword: Primary amines

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Ion Pair Extraction of Aliphatic Amines and Quaternary Ammonium Salts by Picric Acid (Picric Acid에 의한 지방족 아민류와 4급 암모늄 염류의 이온쌍 추출)

  • 김박광;이종숙;장성기;나운용;옥치환
    • YAKHAK HOEJI
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    • v.35 no.3
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    • pp.182-189
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    • 1991
  • Systematic study on the extraction of ion pair by the use of picric acid (PCA) as an ion pair forming reagent to the aliphatic amines has not be done by spectrophotometric method. The extraction of ion pair by the use of PCA and 23 kinds of the aliphatic amines was examined. The procedure is as follows; Elving's buffer solution (pH 1.3~10, ionic strength 0.5) each amine solution, and PCA solution were taken into a test tube. The mixture was shaken mechanically with chlorform. The organic phase was filtered through a filter paper to remove water droplets. The absorbance was examined at $\lambda_{max}$ against a reagent blank. Primary and secondary whose carbon number were more than 7 or 6, respectively, are extractable as ion pairs with PCA, while tertiary amines and quaternary ammonium salts are also extractable without the correlation of carbon number. It was considered that the ion pair extraction of primary and secondary amines was affected by the number of carbon of amines, but its extraction of tertiary amines or quaternary ammonium salts was affected by kind of aliphatic amines rather than pKa values or carbon number of amines.

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Dissociation Constant of the Primary Amines and Quaternary Ammonium-methylorange Salts.

  • Kim, Bak-Kwang
    • YAKHAK HOEJI
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    • v.18 no.3
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    • pp.197-202
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    • 1974
  • The data pf dosspcoatopm cpmstamts for aliphatic amines and quaternary ammonium-methylorange salts are based on the electrosatic theory of conductance. Dissociation constants for primary amines nad quaternary ammonium-methylorange salts (1$\times$10$^{-5}$~1$\times$10$^{-3}$ M) in nitrobenzene solution or water solution was evaluated from the relation of the concentration and the electric conduction and the electric conductance at $25^{\circ}C$ Plots of ${\delta}C$ against reciprocal conductance were linear ; hence the center-to-center distance of this salt was 1.75 $\AA$ in nitrobenzene solution.

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An Efficient Method for N-Formylation of Amines Using Natural HEU Zeolite at Room Temperature Under Solvent-Free Conditions

  • Bahari, Siavash;Mohammadi-Aghdam, Babak;Mohammad Sajadi, S.;Zeidali, Fereshteh
    • Bulletin of the Korean Chemical Society
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    • v.33 no.7
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    • pp.2251-2254
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    • 2012
  • A rapid and practical green route for N-formylation of primary and secondary amines with formic acid at room temperature under the solvent-free conditions using HEU zeolite as a heterogeneous, reusable and highly efficient catalyst is described. The process is remarkably simple and environmentally benign. Excellent chemoselectivity was observed for the conversion of primary amines in the presence of secondary amines.

Synthesis of N-Substituted Isoindolin-1-ones via Palladium-Catalyzed Carbonylative Heterocyclization of o-Bromobenzylbromide with Carbon Monoxide and Primary Amines

  • 심상철;Li Hong Jiang;이동엽;조찬식
    • Bulletin of the Korean Chemical Society
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    • v.16 no.11
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    • pp.1064-1067
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    • 1995
  • A convenient method for the synthesis of N-substituted isoindolin-1-ones is disclosed in palladium(0)-catalyzed heterocyclization of o-bromobenzylbromide with carbon monoxide (CO) and primary amines in DMF at 100 ℃.

Ruthenium Catalyzed Synthesis of 1-Substituted Perhydroazocines from Primary Amines and 1,7-Heptanediol

  • Shim, Sang-Chul;Doh, Chil-Hoon;Yoon, Jeum-Ho;Lee, Dong-Yub;Youn, Young-Zoo
    • Bulletin of the Korean Chemical Society
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    • v.12 no.6
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    • pp.649-652
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    • 1991
  • The reaction of primary aromatic amines with 1,7-heptanediol in the presence of a catalytic amount of ruthenium complex in dioxane at $180^{\circ}C$ for 24 hours gave the corresponding 1-substituted perhydroazocines in moderate yield.

Promotion of Asexual Development and Inhibition of Sexual Development of Aspergillus nidulans by Short-Chain Primary Amines

  • Song, Myung-Hoon;Kuppusamy Selvam;Park, Chang-Jun;Jahng, Kwang-Yeop;Han, Dong-Min;Chae, Keon-Sang
    • Journal of Microbiology
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    • v.40 no.3
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    • pp.230-233
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    • 2002
  • Effects of short-chain primary amines on Aspergillus nidulans development were analyzed. Propylamine induced asexual development and inhibited sexual development. Even on medium containing lactose as the sole carbon source, on which little conidial heads are formed and sexual structures are formed preferentially, or when sexual development was induced, propylamine induced asexual development and inhibited sexual development. These effects of propylamine seemed to be due to accumulation of mRNA of the brlA gene, which has been identified as a positive regulator of asexual development, and due to the reduction of the veA mRNA level. The veA gene has been identified as an activator of sexual development and also as an inhibitor of asexual development. Other primary amines, methylamine and ethylamine, showed identical effects on development where short-chain primary amino also promoted asexual development and inhibited sexual development.

Solvent Free N-Heterocyclization of Primary Amines to N-Substituted Azacyclopentanes Using Hydrotalcite as Solid Base Catalyst

  • Dixit, Manish;Mishra, Manish;Joshi, P.A.;Shah, D.O.
    • Bulletin of the Korean Chemical Society
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    • v.33 no.5
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    • pp.1457-1464
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    • 2012
  • An ecofriendly catalytic route for selective synthesis of $N$-substituted azacyclopentanes, nitrogen-containing heterocyclic intermediates for many bioactive compounds, was established by carrying out $N$-heterocyclization (di $N$-alkylation) of primary amines with 1,4-dichloro butane (as dialkylating agent) using catalytic amount of hydrotalcite as solid base catalyst. The hydrotalcite was found to be efficient solid base catalyst for di $N$-alkylation of different primary amines (aniline, benzyl amine, cyclohexyl amine and n-butyl amine) giving 82 to 96% conversion (at optimized reaction condition) of 1,4-dichloro butane and > 99% selectivity of respective $N$-substituted azacyclopentanes within 30 min. under solvent free condition. The reaction parameters significantly influence the conversion of 1,4-dichloro butane to $N$-substituted azacyclopentanes. The nature of substituent present on amino group affects the reactivity of amine substrates for di $N$-alkylation reaction with 1,4-dichloro butane. The 1,4-dichloro butane was found to be highly reactive alkylating agent for di $N$-alkylation of amines as compared to 1,4-dihydroxy butane. The reusability of the catalyst and its chemical stability in the reaction was demonstrated.

Liquid Phase Adsorption Equilibria of Amines onto High Silica Zeolite, Macroreticular Resin and Granular Activated Carbon (고시리카제올라이트, 거대망상수지 및 입상활성탄에 의한 아민류의 액상흡착평형)

  • Lee, Sung-Sik;Kim, Hyung-Jun;Yu, Myung-Ho
    • Applied Chemistry for Engineering
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    • v.9 no.5
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    • pp.661-666
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    • 1998
  • Liquid phase adsorption equilibria of amines in an aqueous solution onto high silica zeolite pellets (HSZ), macroreticular resin particles (MR) and granular activated carbon (GAC) were determined using a batch bottle technique at 298K. The isotherm curves of HSZ-amines and GAC-amines indicate the nonlinear relationship of unfavorable adsorption type of HSZ-amines and favourable one of GAC-amines. However the curves of MR-amines represent the linear pattern of an adsorption isotherm. Among various equilibrium isotherms, the three parameters of the Redlich-Peterson equation and the two parameters of the Freundlich equation are found to be the most satisfactory within the range of this study. The two parameters of the Langmuir isotherm were not applicable to the present adsorption systems. The amines were adsorbed on the HSZ, MR and GAC in the following sequence of adsorptivity; aromatic amines > primary amines > secondary amines. The product of the Freundlich constants, k and n, proportionally increased with the boiling point, molar volume and dissociation constants of amines adsorbed on HSZ, MR and GAC.

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Synthesis and Characterization of a Hydroxylated Dendrimeric Gene Delivery Carrier

  • Kim, Tae-Il;Bai, Cheng-Zhe;Park, Jong-Sang
    • Bulletin of the Korean Chemical Society
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    • v.28 no.8
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    • pp.1317-1321
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    • 2007
  • Arginine conjugated PAMAM dendrimer, PAMAM-R was modified with propylene oxide via hydroxylation of primary amines of arginine residues. About 49 amines were detected to be converted to amino alcohols by 1H NMR. The newly synthesized polymer, PAMAM-R-PO was able to completely retard pDNA from a charge ratio of 2. The average diameter of PAMAM-R-PO polyplex was found to be 242 nm at a charge ratio of 30. The Zeta-potential value of PAMAM-R-PO polyplex was able to reach 20-30 mV over a charge ratio of 10. PAMAM-R-PO indicated higher cell viability than unmodified PAMAM-R on HeLa and 293 cells because of its hydroxylated amines. Transfection experiments on 293 cells showed that the transfection efficiency of PAMAM-R-PO was found to be 1.5-1.9 times higher than that of PEI25kDa at a charge ratio of 30. The polymer eventually displayed about 2 times greater transfection efficiency than PAMAM-R at the same charge ratio in the absence of serum. Therefore, we concluded that the modification of primary amines of PAMAMR to amino alcohols gives positive effects such as reduced cytotoxicity and enhanced transfection efficiency on 293 cells for gene delivery potency of PAMAM-R.

Four-Component Synthesis of 2-(N,N-Dialkylamino)-2,4,6-Cycloheptatrien-1-One Derivatives from Tropolone, an Isocyanide, a Primary Amine and an Aldehyde via Ugi-Smiles Coupling Reaction

  • Massoudi, Abdolhossain;Amini, Issa;Ramazani, Ali;Nasrabadi, Fatemeh Zeinali;Ahmadi, Yavar
    • Bulletin of the Korean Chemical Society
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    • v.33 no.1
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    • pp.39-42
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    • 2012
  • The use of Smiles rearrangement in Ugi-type couplings with tropolone allows very straightforward multicomponent formation of 2-(N,N-dialkylamino)-2,4,6-cycloheptatrien-1-one derivatives. The Ugi four-component reaction of isocyanides with tropolone (2-hydroxy-2,4,6-cycloheptatrien-1-one), primary amines and aldehydes proceeds smoothly and cleanly under mild conditions to afford 2-(N,N-dialkylamino)-2,4,6-cycloheptatrien-1-one derivatives in fairly good yields.