• Title/Summary/Keyword: Nitro groups

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Selective Reduction by Lithium Bis- or Tris(dialkylamino)aluminum Hydrides. VIII. Reaction of Lithium Tripiperidinoaluminum Hydride in Tetrahydrofuran with Selected Organic Compounds Containing Representative Functional Groups

  • 차진순;이재철;주영철
    • Bulletin of the Korean Chemical Society
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    • v.18 no.8
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    • pp.890-895
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    • 1997
  • The approximate rates and stoichiometry of the reaction of excess lithium tripiperidinoaluminum hydride (LTPDA), an alicyclic aminoaluminum hydride, with selected organic compounds containing representative functional groups under the standardized conditions (tetrahydrofuran, 25°) were examined in order to define the reducing characteristics of the reagent for selective reductions. The reducing ability of LTPDA was also compared with those of the parent lithium aluminum hydride (LAH) and lithium tris(diethylamino)aluminum hydride (LTDEA), a representative aliphatic aminoaluminum hydride. In general, the reactivity of LTPDA toward organic functionalities is weaker than LTDEA and much weaker than LAH. LTPDA shows a unique reducing characteristics. Thus, benzyl alcohol, phenol and thiols evolve a quantitative amount of hydrogen rapidly. The rate of hydrogen evolution of primary, secondary and tertiary alcohols is distinctive. LTPDA reduces aldehydes, ketones, esters, acid chlorides and epoxides readily to the corresponding alcohols. Quinones, such as p-benzoquinone and anthraquinone, are reduced to the corresponding diols without hydrogen evolution. Tertiary amides and nitriles are also reduced readily to the corresponding amines. The reagent reduces nitro compounds and azobenzene to the amine stages. Disulfides are reduced to thiols, and sulfoxides and sulfones are converted to sulfides. Additionally, the reagent appears to be a good partial reducing agent to convert primary carboxamides into the corresponding aldehydes.

Reaction of Lithium Gallium Hydride with Selected Organic Compounds Containing Representative Functional Groups

  • Choe, Jeong Hun;Yun, Mun Yeong;Yun, Jong Hun;Jeong, Dong Won
    • Bulletin of the Korean Chemical Society
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    • v.16 no.5
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    • pp.416-421
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    • 1995
  • The approximate rates and stoichiometry of the reaction of excess lithium gallium hydride with selected organic compounds containing representative functional groups were examined under the standard conditions (diethyl ether, 0 $^{\circ}C)$ in order to compare its reducing characteristics with lithium aluminum hydride and lithium borohydride previously reported, and enlarge the scope of its applicability as a reducing agent. Alcohols, phenol, and amines evolve hydrogen rapidly and quantitatively. However lithium gallium hydride reacts with only one active hydrogen of primary amine. Aldehydes and ketones of diverse structure are rapidly reduced to the corresponding alcohols. Conjugated aldehyde and ketone such as cinnamaldehyde and methyl vinyl ketone are rapidly reduced to the corresponding saturated alcohols. p-Benzoquinone is mainly reduces to hydroquinone. Caproic acid and benzoic acid liberate hydrogen rapidly and quantitatively, but reduction proceeds slowly. The acid chlorides and esters tested are all rapidly reduced to the corresponding alcohols. Alkyl halides and epoxides are reduced rapidly with an uptake of 1 equiv of hydride. Styrene oxide is reduced to give 1-phenylethanol quantitatively. Primary amides are reduced slowly. Benzonitrile consumes 2.0 equiv of hydride rapidly, whereas capronitrile is reduced slowly. Nitro compounds consumed 2.9 equiv of hydride, of which 1.9 equiv is for reduction, whereas azobenzene, and azoxybenzene are inert toward this reagent. Cyclohexanone oxime is reduced consuming 2.0 equiv of hydride for reduction at a moderate rate. Pyridine is inert toward this reagent. Disulfides and sulfoxides are reduced slowly, whereas sulfide, sulfone, and sulfonate are inert under these reaction conditions. Sulfonic acid evolves 1 equiv of hydrogen instantly, but reduction is not proceeded.

Performance of Cement Paste Incorporating Oxidized MWCNT after Nitro-Sulfuric Acid treatment (질산 처리 후 산화된 MWCNT를 혼입한 시멘트 페이스트의 성능)

  • Tugelbayev, Aidyn;Kim, Ji-Hyun;Chung, Chul-Woo
    • Proceedings of the Korean Institute of Building Construction Conference
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    • 2022.04a
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    • pp.243-244
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    • 2022
  • Recently, the utilization of carbon nanotubes (CNT) in cement paste has been widely investigated in terms of improving the dispersion quality and enhancing the cement paste mechanical performance. While methods of functionalizing the CNT using surfactants to disperse the nanoparticles have been studied to some extent, the literature on the effects of chemical covalent functionalization is still scarce. This work focuses on chemical functionalization of multiwall carbon nanotubes (MWCNT) using acid treatment, and a consequent addition of the modified MWCNT to the cement paste. The microstructural observation and degree of the MWCNT functionalization are examined using FE-SEM. The compressive strength is measured at an age of 28 days. The results of the study suggest that the acid-functionalized MWCNT are dispersed better compared to the pristine MWCNT due to presence of functional groups. The better dispersion of the nanotubes and the attached functional groups may contribute to the refinement of the microstructure of the cement paste and hence, increase its mechanical strength.

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Standoff Raman Spectroscopic Detection of Explosive Molecules

  • Chung, Jin Hyuk;Cho, Soo Gyeong
    • Bulletin of the Korean Chemical Society
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    • v.34 no.6
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    • pp.1668-1672
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    • 2013
  • We developed a standoff Raman detection system for explosive molecules (EMs). Our system was composed of reflective telescope with 310 mm diameter lens, 532 nm pulse laser, and Intensified Charge-Coupled Device (ICCD) camera. In order to remove huge background noise coming from ambient light, laser pulses with nanosecond time width were fired to target sample and ICCD was gated to open only during the time when the scattered Raman signal from the sample arrived at ICCD camera. We performed standoff experiments with military EMs by putting the detector at 10, 20 and 30 m away from the source. The standoff results were compared with the confocal Raman results. Based on our standoff experiments, we were able to observe the peaks in the range of 1200 and $1600cm^{-1}$, where vibrational modes of nitro groups were appeared. The wave numbers and shapes of these peaks may serve as good references in detecting and identifying various EMs.

프탈로시아닌 유도체 합성 및 광학응답특성 연구

  • Lee, Jun-Hui;Wang, Sheng;Son, Yeong-A
    • Proceedings of the Korean Society of Dyers and Finishers Conference
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    • 2011.03a
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    • pp.67-67
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    • 2011
  • Recently, Phthalocyanine dye has attentions due to their excellent photochemical properties and used to optical applications such as chemical sensors. And azo groups can change photochemical properties in the UV irradiation because their molecualr structure reverse cis-trans isomer and changes cooperative motion, aggregation and so on. In this study, we synthesized the azo compound between amino pyridine and phenol. this azo derivative used the combination with 3-nitro phthalonitrile and makes phthalocyanine structure through the synthesis with 1,8-diazabicyclo[5.4.0]undec-7-ene(DBU), zinc acetate. Finally, we synthesized a new photoswiching dye zinc-phthalocyanine azo compound. This compound was studied by phothoswichiing phenomenon by UV irradiation and analyzed molecular aggregation through the SEM images.

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SEM Images of Naphthalic Amide Derivatives Appearing by the Substituent Effect of Ending Group

  • Phung, Doan Minh;Jeong, Woo-Chul;Choi, Chang-Shik;Lee, Ki-Hwan
    • Rapid Communication in Photoscience
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    • v.1 no.1
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    • pp.11-12
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    • 2012
  • The naphthalic amide derivatives were synthesized by simple condensation and were crystallized by acetonitrile solution. The SEM images of products with methyl group and nitro group, respectively, showed rod shape while the SEM images of products with other groups ($N(CH_3)_2$, $OCH_3$, H, F, and Cl), respectively, showed plate shape. We were known from these results that the substituent of ending group played an important role in the crystallization of single molecule and the morphology of naphthalic derivatives could be controlled by only change of ending group in single molecule.

Inhibitory Activity of 8-Aminowogonin Analogues Against Prostaglandin $E_2$ Production (8-아미노우고닌 유도체의 Prostaglandin $E_2$ 생성에 대한 저해작용)

  • Jang, Jin-Hee;Sin, Kwan-Seog;Kim, Hyun-Pyo;Park, Hae-Il
    • YAKHAK HOEJI
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    • v.52 no.1
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    • pp.85-91
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    • 2008
  • 8-Acyl and 8-sulfonylamidowogonin analogues were synthesized as potential anti-inflammatory agents. Nitration of 5,7-dihydroxyflavone (chrysin) followed by methylation of phenol groups and reduction of nitro group yielded 8-aminowogonin analogues. Acylation and sufonylation of 8-aminowogonin followed by demethylation reactions gave the title compunds. The synthesized wogonin analogues showed much reduced inhibitory activity on prostaglandin $E_2\;(PGE_2)$ production.

Studies of 8-Hydroxyquinoline Derivatives (Part I) Synthesis of 7-Nitroso-8-Hydroxyquinoline-5-Sulfonate and its Acid Dissociation Constants (8-Hydroxyquinoline 誘導體에 關한 硏究 (第 1 報) 7-Nitroso-8-Hydroxyquinoline-5-Sulfonate 의 合成과 그 酸解離定數)

  • Lee, Dong-Hyung
    • Journal of the Korean Chemical Society
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    • v.9 no.1
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    • pp.37-40
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    • 1965
  • 7-Nitro-8-hydoxyquinoline-5-sulfonate (NHQS) have been synthesized from 8-hydroxyquinoline-5-sulfonic acid by nitrosation in alkaline medium at temperature below $10^{\circ}C$ and the acid dissociation constants of NHQS have been determined by spectrophotometric and potentiometric methods. Almost same values are obtained by both methods but the values are lower than the corresponding 8-hydroxyquinoline. The lower basicity of NHQS is considered as the effect of electron withdrawing groups, especially adjacent nitroso group.

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A Predictive Study on Molecular and Explosive Properties of 1-Aminoimidazole Derivatives

  • Cho, Soo-Gyeong
    • Bulletin of the Korean Chemical Society
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    • v.32 no.7
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    • pp.2319-2324
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    • 2011
  • Molecular structures and chemical properties of 1-aminoimidazole derivatives have been investigated at high levels of density functional theories. Heat of formation, density, explosive performances and impact sensitivities have been estimated at the global minimum of potential energy surface. As more nitro groups are introduced, the explosive performances of 1-aminoimidazole derivatives are enhanced, while the impact sensitivity becomes more sensitive. A two-dimensional plot between explosive performance and impact sensitivity has been utilized to comprehend the technical status of new explosive candidates. Based on locations in the two-dimensional plot, 1-aminodinitroimidzole isomers appears to have a potential to be good candidates for insensitive explosives, and 1-aminotrinitroimidazole may become a powerful explosive molecule whose behavior is quite close to HMX.

5-Arylidene-2(5H)-Furanone Derivatives: Synthesis and Structure-Activity Relationship for Cytotoxicity

  • Bang, Seong-Cheol;Kim, Yong;Yun, Mi-Young;Ahn, Byung-Zun
    • Archives of Pharmacal Research
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    • v.27 no.5
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    • pp.485-494
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    • 2004
  • Thirty-eight 5-arylidene-2(5H)-furanone derivatives possessing halo-, methoxy-, oxo-, dioxo-, and thiophenyl groups as well as anthraquinone and naphthquinone moieties were synthesized, and their cytotoxicity was evaluated against various cancer cell lines. The introduction of halogen atoms or nitro group at aromatic ring of 5-arylidene-2(5H)-furanone was shown to increase the cytotoxicity with 5-(3-nitrobenzylidene )-2(5H)-furanone (21) being the most potent. Among anthracenyl or naphthalenyl derivatives, (E)-5-[2-(1 ,4-dimethoxy-9, 10-dioxo) anthracenyl]-2(5H)-furanone (34) showed the most potent cytotoxic activity.