• Title/Summary/Keyword: phthalimide

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A Study on Antimicrobial Activity of N-(fluorodichlomethylthio) Phthalimide-Ag Complex of Reclaimed Rubber Mat (리사이클 고무 매트의 N-(fluorodichlomethylthio) Phthalimide-Ag Complex에 관한 항미생물 활성 연구)

  • Kim, Ki-Jun;Lee, Joo-Youb;Park, Tae-Sul
    • Journal of the Korean Applied Science and Technology
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    • v.28 no.4
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    • pp.491-496
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    • 2011
  • N-(fluorodichlomethylthio) phthalimide-silver complexes were prepared and investigated the antimicrobial activity on rubber mat manufactured with waste rubber. We are exposed to harmful bacteria and fungi all the time. We manufactured antimicrobial mat to be imposed to mats that it can prevent generation of bacteria and microorganisms, and restrict their reproduction. Infection of medical devices causes significant morbidity and mortality. For aim of this study, we measured the antimicrobial mat manufactured with N-(fluorodichlomethylthio) phthalimide-Ag complex by CCD, FT-IR and NMR. The effect of mole ratio of N-(fluorodichlomethylthio) phthalimide-Ag complex on antibacterial activity to bacteria and fungi is investigated. Reduction rate is evaluated using the Quinn method. Escherichia Coli is effectively inhibited than Staphylococcus aureus by antimicrobial mat.

Electrical Behaviour of Some Phthalimide Derivatives and Their Complexes with Transition Metals

  • Mohamed Gamal Abd Ei Wahed;Kamel Ei Manakhly;Hamdy Hammad;Atiat Barakat
    • Bulletin of the Korean Chemical Society
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    • v.17 no.3
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    • pp.285-288
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    • 1996
  • The electrical conductivity of some phthalimide derivatives and their complexes with Co(II), Ni(II), Cu(II), or Zn(II) has been measured in the temperature range 290-435 K. Both the structure of phthalimide molecule and its complexes played an effective role in the conduction process. Conductometric titration and IR spectra were used to characterize the structure of studied samples.

The Synthesis of $\alpha$-lhnctionalized Benzykmine ($\alpha$-Functionalized Benzylamine의 합성)

  • Kim, Hyeung-Jae;Cho, Su-Dong;Ahn, Chul Jin;Joo, Woo-Hong;Shin, Dong Soo
    • Journal of the Korean Chemical Society
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    • v.44 no.5
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    • pp.442-447
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    • 2000
  • $\alpha$-Functionalized benzylamine(Nu=OAc, OMe, N$_3$) will be very usefud as a starting material or synton in organic synthesis. We have investigated the first synthetic methodology of phthalimide-ben-zylacetate from benzylphthalimide, which are prepared in NBS/NaOAc/HOAc in chlorobenzene at 137$^{\circ}C$ for 12 hr in good yield. Finally, amino(phenyl)methyl acetate (1) was synthesized from phthalimide-benzyl acetate under NH$_2$NH$_2$/HOAC.

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Photocyclization Reactions of N-(Trimethylsilylmethoxyalkyl)Phthalimides. Efficient and Regioselective Route to Heterocycles

  • Yoon Ung Chan;Oh Ju Hee;Lee, Sang Jin;Kim, Dong Uk;Lee, Jong Gun;Kang Kyung-Tae;Mariano Patrick S.
    • Bulletin of the Korean Chemical Society
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    • v.13 no.2
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    • pp.166-172
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    • 1992
  • Studies have been conducted to explore single electron transfer (SET) induced photocyclization reactions of N-(trimethylsilylmethoxyalkyl)phthalimides(alkyl=E thyl, n-propyl, n-butyl, n-pentyl, and n-octyl). Photocyclizations occur in methanol in high yields to produce cyclized products in which phthalimide carbonyl carbon is bonded to the carbon of side chain in place of the trimethylsilyl group. Mechanism for these photocyclizations involving intramolecular SET from oxygen in the $\alpha-silylmethoxy$ groups to the singlet excited state phthalimide moieties followed by desilylation of the intermediate $\alpha-silylmethoxy$ cation radicals and cyclization by radical coupling are proposed. In contrast, photoreaction of N-(trimethylsilylmethoxyethyl) phthalimide in acetone follows different reaction routes to produce two cyclized products in which carbon-carbon bond formation takes place between the phthalimide carbonyl carbon and the carbon $\alpha$ to silicon and oxygen atoms via triplet carbonyl hydrogen abstraction triplet carbonyl silyl group abstraction pathways. The normal singlet SET pathway dominates these triplet processes for photoreaction of this substance in methanol. The efficient and regioselective cyclization reactions observed for photolysis in methanol represent synthetically useful processes for construction of medium and large ring heterocyclic compounds.

A Study on Spin-Lattice Relaxation of Methyl Protons in 2,6-Dichlorotoluene and N-Methyl Phthalimide

  • Lee, Jo-Woong;Lim, Man-Ho;Rho, Jung-Rae
    • Bulletin of the Korean Chemical Society
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    • v.12 no.1
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    • pp.47-51
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    • 1991
  • Spin-lattice relaxation of methyl protons in 2,6-dichlorotoluene and N-methyl phthalimide, each dissolved in CDCl$_3$, has been studied at 34$^{\circ}$C and the contribution from spin-rotation interaction to the relaxation process has been separated from that due to dipole-dipole interactions among methyl protons. The results show that the spin-rotational contributions to the initial rate of relaxation in 2,6-dichlorotoluene and N-methyl phthalimide amount to 18 and 31%, respectively, of the total relaxation rate at 34$^{\circ}$C. The method of separating the spin-rotational contribution from that of dipolar interactions adopted in this paper is based on the well known fact that in an A$_3$ spin system such as methyl protons in liquid phase dipolar relaxation mechanism gives non-exponential decay of the z-component of total magnetization of protons while the random field fluctuation such as spin-rotational mechanism causes exponential decay.

Preparation of Poly(imide-aramid-sulfone)s and their Thermal Properties (폴리(이미드-아라미드-설폰)의 합성과 그들의 열적성질)

  • Park, Hyung-Seok;Gong, Myoung-Seon
    • Polymer(Korea)
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    • v.36 no.4
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    • pp.427-433
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    • 2012
  • A series of poly(imide-aramid-sulfone)s with alternatingly introduced imide/aramid groups were prepared by reacting divinyl sulfone (DVS) and $N^1,N^4$-bis(4-(vinylsulfonyl)phenyl)terephthalamide (2) with pyromellitic diimide. Three model compounds, N-[2-(p-aminophnenylsulfonyl)ethyl]phthalimide (3), 2,2'-(2,2'-sulfonylbis(ethane-2,1-diyl))diisoindoline-1,3-dione (4), and N,N-bis(4-(2-(1,3-dioxoisoindolin-2-yl)ethylsulfonyl)phenyl)terephthalamide (5), resembling polymers were prepared with good yields by reacting p-aminophenyl vinyl sulfone, DVS, and 2 with phthalimide. Condensation polymerization was carried out by Michael-type addition reaction of the difunctional phthalimide group with the DVS group in the presence of tetrabutylammonium hydroxide (TBAH), resulting in poly(imide-aramid-sulfone)s 6-12 with moderate molecular weights and good yields. They were highly soluble in polar solvents such as N,N-dimethylformamide, dimethylsulfoxide, N-methylpyrrolidinone and tetrahydrofuran. The ratios of DVS/2 were 1/0, 3/1, 2/1, 1/1, 1/2, 1/3, and 0/1. Molecular weight and physical properties such as solubility, viscosity, and thermal properties of the polymers were examined.

Exploratory Study of Photocyclization Reactions of N-(Trimethylsilylmethylthioalkyl)phthalimides

  • Ung Chan Yoon;Sang Jin Lee;Kyung Ja Lee;Sung Ju Cho;Chan Woo Lee;Patrick S. Mariano
    • Bulletin of the Korean Chemical Society
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    • v.15 no.2
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    • pp.154-161
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    • 1994
  • Studies have been conducted to explore single electron transfer (SET) induced photocyclization reactions of N-(trimethylsilylmethylthioalkyl)phthalimides (alkyl=ethyl, n-propyl, n-butyl, n-pentyl, and n-hexyl). Photocyclizations occur in methanol in modest to high yields to produce cyclized products in which phthalimide carbonyl carbon is bonded to the carbon of side chain in place of the trimethylsilyl group. Mechanism for these photocyclizations involving intramolecular SET from sulfur in the ${\alpha}$-silylmethylthioalkyl groups to the singlet excited state phthalimide moieties followed by desilylation of the intermediate ${\alpha}$ -silylmethylthio cation radicals and cyclization by radical coupling is proposed. In contrast, photoreactions of N-(trimethylsilylmethylthioalkyl)phthalimides in acetone follow different reaction routes to produce another cyclized products in which carbon-carbon bond formation takes place between the phthalimide carbonyl carbon and the carbon ${\alpha}$ to silicon and sulfur atoms via triplet carbonyl hydrogen abstraction pathway. The normal singlet SET pathway dominates this triplet process for photoreactions of these substances in methanol while the triplet process dominates the singlet SET pathway for those in acetone. The efficient and regioselective cyclization reactions observed for photolyses in methanol represent synthetically useful processes for construction of medium and large ring heterocyclic compounds.

Studies on the effect of phthalimido methyl-O,O-dimethyl-phosphorodithioate (Imidan) and its possible metabolites on the growth of rice plant (Phthalimido methyl-O,O-dimethyl phosphorodithioate (Imidan)과 그의 대사물질(代謝物質)이 수도(水稻) 생육(生育)에 미치는 영향(影響)에 관(關)한 연구(硏究))

  • Lee, Sung-Hwan;Lee, Dong-Suk;Lee, Jae-Koo
    • Applied Biological Chemistry
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    • v.7
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    • pp.105-117
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    • 1966
  • This experiment was conducted to investigate the effet of phthalimido-methyl-O,O-dimethyl-phosphorodithioate (Imidan) known as an acaricide and its possible metabolic products on the growth of plant, when sprayed on the leaves of rice plant. The results are summarized as follows. 1) Possible metabolic products of Imidan, the following compounds were synthesized or recrystallized for the present experiment a) N-Hydroxymethyl phthalimidem b) Phthalimide c) Phthalamidic acid d) Phthalic acid e) Anthranilic acid f) p-Amino benzoic acid g) p-Hydroxy benzoic acid h) Benzoic acid 2) Among the above materials, a), c), d), e), and Imidan were dissolved in a buffer solution respectively to be 10 and 20 p.p.m. and tested with the wheat coleoptile straight growth method. According to the results, Imidan inhibited the growth of coleoptile in both 10 and 20 p.p.m., whereas the others showed much better growth than the control, especially phthalamidic acid in 10 p.p.m. It appears that Imidan itself inhibits the coleoptile growth, whereas the metabolites derived from Imidan through various metabolisms, including hydrolysis in plant tissues show growth-regulating activity. (refer: Table 1, Fig. 1) 3) 20, 100 and 200 p.p.m. solutions of Imidall emulsion in xylene f·ere prepared. The lengths of shoot and root of rice seeds germinated on the re-respective media were measured after 12 days. The data showed that root was much more elongated in Imidan 20 p.p.m., whereas shoot in Imidan 100 p.p.m., respectively, than in the xylene control. An interesting finding was that xylene used as solvent had a tendency to inhibit seriously the root growth of rice seed. (refer: Table 2,5). 4) The emulsions of concentrations in 10, 25, 50 and 100 p.p.m's of control, Imidan, N-hydroxy methyl phthalimide, anthranilic acid, and phthalmide, respectively, were sprayed twice on the rice plant on pot. After a certain period of time lengths of rice culms were measured, showing that plots treated with Imidan and N-hydroxy methyl phthalimide exhibited much more growth than those of control and the others. 5) Loaves and stems of rice plant were sampled and extracted with dried acetone at the intervals of 3-, 5-, 7-, and 14 days after treated with Imidan 250 p.p.m. emulsion. This sample extracted with acetone was purified by means of prechromatographic purification method with acetonitrile and paperchromatographed to detect the following metabolic products. Imidan (Rf: 0.97-0,98), N-hydroxy-methyl phthalimide (Rf: 0.87) phthalimide (Rf: 0.86-0.87), phthalamidic acid (Rf: 0.13-0.14), phthalic acid (Rf: 0.02-0.03), benzoic acid (Rf: 0.42-0.43), p-amino benzoic acid or p-hydroxy benzoic acid (Rf: 0.08-0.09), and unidentified compounds (Rf: 0.73, 0.59, 0.33, 0.23. 0.07). In addition, in the early stages, such as 3- and 5 days nonhydrolyzed Imidan and its first hydrolytic product, N-hydroxymethyl phthalimide were detected in relatively large amounts, whereas in the last stages of 7- and 14 days due to further decomposition, the afore-mentioned two materials were reduced in the amount and p-hthalic, phthalamidic, benzoic, and p-Hydroxy benzoic, or p-Amino benzoic acids were detected in a considerably large amount. It is, therefore, believed that most of Imidan applied to the leaves of rice plant may be decomposed within almost 14 days. In the light of above observations it is considered that Imidan itself is not involved in plant growth regulating activity, whereas various phthaloyl derivatives produced in the course of metabolism (namelr, enzymic action) in plant tissues may have such effect.

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