• Title/Summary/Keyword: Nitro group

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EXPLORATORY PHOTOCHEMICAL STUDY ON THE o-NITROBENZYLSULFONYL DERIVATIVES

  • Chang, Sun-Ki
    • Journal of Photoscience
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    • v.1 no.1
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    • pp.67-68
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    • 1994
  • INTRODUCTION : The photochemistry of nitro chromophore has been the subject of intense study only in recent years. Unlike the carbonyl functional group, of which the photochemistry has been quite extensively studied and fairly well understood, as a result of excellent work done by numerous physical and organic photochemists alike, the nature of photochemistry of nitro group has only recently been systematically explored. The photochemistry of nitro group exhibits general features of the photochemistry of the carbonyl groups such as hydrogen abstraction by the diradical species generated from the n-$\pi$$^*$ excited state of the nitro group. Other photochemical pathways common to the carbonyl group such as the biradical intermidiate formation, photocycloelimination, and cydoaddition reactions are also open for the nitro group. Of all the photochemical reactions of the nitro group mentioned above, hydrogen abstraction by the n-$\pi$$^*$ excited state of the nitro group has drawn much attention by synthetic organic chemists and polymer chemists. In the field of organic synthesis, above mintioned photochemical reaction has been utilized in the photoprotection-deprotection chemistry.

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The Frequency-Dependent First-, Second-, and Third-Order Polarizabilities of Thiophene-, Furan-, Pyrrole-Nitro Polyene Systems

  • Choe, Yu Seong
    • Bulletin of the Korean Chemical Society
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    • v.17 no.1
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    • pp.61-65
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    • 1996
  • The semiempirical time-dependent Hartree-Fock PM3 calculations have been performed on three polyene systems. In order to study the nonlinear optical properties, we calculated the frequency-dependent first-, second-, and third-order polarizabilities of thiophene-, furan-, pyrrole-nitro polyene systems. The PM3 predicted average and longitudinal polarizabilties increase in the order: thiophene- > pyrrole- > furan-nitro polyene systems. The PM3 predicted limiting average second-order polarizabilities show the order: pyrrole- > furan- > thiophene-nitro polyene systems. The average and longitudinal third-order polarizabilties have the following order: pyrrole- > thiophene- > furan-nitro polyene systems. In these trends, we sugest that pyrrole group is the best donor group among the three polyene systems.

Catalytic Hydrogenation of Aromatic Nitro Compounds over Borohydride Exchange Resin Supported Pd (BER-Pd) Catalyst

  • Yoon, Nung-Min;Lee, Hyang-Won;Choi, Jae-Sung;Lee, Hyun-Ju
    • Bulletin of the Korean Chemical Society
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    • v.14 no.2
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    • pp.281-283
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    • 1993
  • Aromatic nitro compounds are selectively hydrogenated to the corresponding amines in high yields at room temperature and atmospheric pressure using BER-Pd catalyst without affecting ketone, ether, ester, nitrile or chloro groups also present. Especially the nitro group in 4-nitrobenzyl alcohol, methyl 4-nitrobenzyl ether and N-N-dimethyl 4-nitrobenzylamine is selectively hydrogenated with this catalyst to give the corresponding amines without hydrogenolysis of benzylic groups. And aromatic nitro compound can be reduced selectively in the presence of aliphatic nitro compound.

The Effects of Sonic Waves on the Reduction of Aromatic Nitro Groups Using Iron, Hydrazine Hydrate and Activated Carbon (유기 초음파화학. 초음파가 히드라진, 철, 활성탄을 이용한 방향족 니트로기의 환원반응에 미치는 영향)

  • Dae Hyun Shin;Byung Hee Han;Sung Yun Cho
    • Journal of the Korean Chemical Society
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    • v.30 no.1
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    • pp.105-108
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    • 1986
  • Ultrasound(50KHz) accelerated the reduction reaction of aromatic nitro group to aromatic amino group in high yield with mild condition using iron, hydrazine hydrate and activated carbon under room temperature and atmospheric pressure. The activated carbon has been used as a mixing material to highly active metals. However, aromatic nitro group does not reduce at all only with iron-hydrazine witliout adding activated carbon even under ultrasonic irradiation. We also discovered that the conversion yield from nitro group to amino group is directly proportional to the amount of activated carbon.

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Synthesis and Characterizations of Bis-Spiropyran Derivatives

  • Lee, Sungmin;Ji, Seungwook;Kang, Youngjong
    • Bulletin of the Korean Chemical Society
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    • v.33 no.11
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    • pp.3740-3744
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    • 2012
  • We synthesized three different derivatives of bis-spiropyran using simple organic reactions with high yields. BSP1, a derivative of bis-spiropyran having a connection at the position 6' and BSP2, a derivative of bis-spiropyran having a connection at the position 5 and BSP3, a derivative of bis-spiropyran containing a dithienylethene group between two spiropyran moieties were synthesized. The optical properties of BSPs were characterized. UV-Vis spectra showed that BSPs exhibit reversible photo-isomerization and the efficiency of photo-isomerization is highly dependent on the position of nitro group. BSPs having nitro group at para position of hydroxy group showed the higher efficiency of photo-isomerization that the one having nitro group at ortho position. The optical microscope images obtained under ultraviolet or visible light exposure demonstrated that the formation of nanorods can be reversibly controlled by optical signal.

Viologen-mediated Reductive Transformations of gem-Bromonitro Compounds and $\alpha$-Nitro Ketones by Sodium Dithionite

  • Kwanghee Koh Park;Won Kyou Joung;Sook Young Choi
    • Bulletin of the Korean Chemical Society
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    • v.14 no.4
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    • pp.461-465
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    • 1993
  • Reductive transformations of gem-bromonitro compounds and ${\alpha}$-nitro ketones were carried out conveniently with sodium dithionite by using dioctyl viologen as an electron-transfer catalyst in dichloromethane-water two-phase system:the bromine atom in gem-bromonitro compounds and the nitro group in ${\alpha}$-nitro ketones are replaced by hydrogen.

Solution Phase Photolyses of Substituted Diphenyl Ether Herbicides under Simulated Environmental Conditions (모조(模造) 환경조건하(環境條件下)에서의 치환(置換) Diphenyl Ether 제초제(除草劑)의 광분해(光分解)에 관(關)한 연구(硏究))

  • Lee, Jae-Koo
    • Applied Biological Chemistry
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    • v.17 no.3
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    • pp.149-176
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    • 1974
  • Eight substituted diphenyl ether herbicides and some of their photoproducts were studied in terms of solution phase photolysis under simulated environmental conditions by using a Rayonet photochemical reactor. The test compounds absorbed sufficient light energy at the wavelength of 300 nm to undergo various photoreactions. All the photoproducts were confirmed by means of tlc, glc, ir, ms, and/or nmr spectrometry. The results obtained are summarized as follows: Solution phase photolysis of C-6989: An exceedingly large amount of p-nitrophenol formed strongly indicates the readiness of the ether linkage cleavage of this compound as the main reaction in all solvents used. Photoreduction of nitro to amino group(s) and photooxidation of trifluoromethyl to carboxyl group were recognized as minor reactions. Aqueous photolysis of p-nitrophenol: Quinone(0.28%), hydroquinone (0.66%), and p-aminophenol (0.42%) were confirmed as photoproducts, in addition to a relatively small amount of an unknown compound. The mechanisms of formation of these products were proposed to be the nitro-nitrite rearrangement via $n{\rightarrow}{\pi}^*$ excitation and the photoreduction through hydrogen abstractions by radicals, respectively. Solution phase photolysis of Nitrofen: Photochemical reduction leading to the p-amino derivative was the main reaction in n-hexane. In aqueous solution, the photoreduction of nitro to amino group and hydroxylation predominated over the ether linkage cleavage. Nucleophilic displacement of the nitro group by hydroxide ion and replacement of chlorine substituents by hydroxyl group or, to a lesser extent, hydrogen were also observed as minor reactoins. Solution phase photolysis of MO-338: Photoreduction of the nitro to amino group was marked in the n-hexane solution photolysis. In the aqueous solution, photoreduction of the nitro substituent and hydroxylation were the main reactions with replacement of chlorine substituents by the hydroxyl group and hydrogen, and cleavage of the ether linkage as minor reactions. Photolyses of MC-4379, MC-3761, MC-5127, MC-6063, and MC-7181 in n-hexane and cyclohexane: Photoreduction of the nitro group leading to the corresponding amino derivative and replacement of one of the halogen substituents by hydrogen from the solvent used were the key reactions in each compound. Aqueous photolysis of MC-4379: Cleavage of the ether linkage, replacement of the carboxymethyl by hydroxyl group, hydroxylation, and replacement of the nitro by hydroxy group were prominent with photoreduction and dechlorination as minor reactions. Aqueous photolysis of MC-3761: Cleavage of the ether linkage, replacement of the carboxymethyl by hydroxyl group, and photoreduction followed by hydroxylation were the main reactions. Aqueous photolysis of MC-5127: Replacement of carboxyethyl by hydrogen was predominant with ether linkage cleavage, photoreduction, and dechlorination as minor reactions. It was obvious that the decarboxyethylation proceeded more readily than decarboxymethylation occurring in the other compounds. Aqueous photolysis of MC-6063: Cleavage of the ether linkage and photodechlorination were the main reactions. Aqueous photolysis of MC-7181: Replacement of the carboxymethyl group by hydrogen and monodechlorination were the remarkable reactions. Cleavage of the ether linkage and hydroxylation were thought to be the minor reactions. Aqueous photolysis of 3-carboxymethyl-4-nitrophenol: The photo-induced Fries rearrangement common to aromatic esters did not appear to occur in the carboxymethyl group of this type of compound. Conversion of nitro to nitroso group was the main reaction.

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Antituberculosis Agents X. Synthesis and Evaluation of In Vitro Antituberculosis Activity of 2-(5-Nitro-2-furyl)-and 2-(1-Methyl-5-nitro-1H-imidazol-2-yl)-1 ,3,4-thiadiazole Derivatives

  • Alireza-Foroumadi;Fatemeh-Soltani;Raheleh-Jabini;Moshafi, Mohammad-Hasan;Rasnani, Fatemeh-Mohammadian
    • Archives of Pharmacal Research
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    • v.27 no.5
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    • pp.502-506
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    • 2004
  • Two series of 2-(5-nitro-2-furyl)- and 2-(1-methyl-5-nitro-1H-imidazol-2-yl)-5-propyl, allyl and propargyl)thio-1,3,4-thiadiazoles (6a-f) and 2-(5-nitro-2-furyl)- and 2-(1-methyl-5-nitro-1 H-imidazol-2-yl)-5-(nitrobenzyl)thio-1,3,4-thiadiazole derivatives (8a-f) have been synthesized and evaluated against Mycobacterium tuberculosis, as part of the TAACF TB screening program under direction of the US National Institute of Health, the NIAID division. Primary screening was conducted at a single concentration, 6.25 $\mu\textrm{g}$mL$^{-1}$ , against M. tuberculosis H$_{37}$ Rv in BACTEC 12B medium, using the Microplate Alamar Blue Assay (MABA). The minimum inhibitory concentration (MIC) was determined for the compounds that demonstrated $\geq$90% growth inhibition in the primary screening. A varying degree of antituberculosis activity (from 0-97% of growth inhibition) was observed with the alkylthio series (6a-f), and the nitroimidazole derivative with a propylthio group (6b) and the nitrofuran derivative with a propargylthio group (6e), were the most active compounds (MIC=3.13 and 1.56 /$\mu\textrm{g}$mL$^{-1}$ , respectively). Among the nitrobenzylthio derivatives (8a-f), all the ortho, meta and para nitrobenzyl isomers in the nitrofuran series exhibited good antituberculosis activity (MIC=3.13 $\mu\textrm{g}$mL$^{-1}$ ), while the corresponding nitroimidazole analogues were completely inactive (Inhibition=0%).

Enhancement of Adenovirus Type 12 Transformation by N-Methyl-N'-Nitro-N-Nitrosoguanidine (N-Methyl-N'-Nitro-N-Nitrosoguanidine에 의한 Adenovirus Type 12 Transformation의 증진)

  • Choi, Sung-Bae
    • The Journal of Korean Society of Virology
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    • v.27 no.2
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    • pp.257-260
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    • 1997
  • Adenoviruses are icosahedral virions containing double-stranded linea DNA. They are 70 nm to 90 nm in diameter and capsid is composed of 252 capsomeres. Several members of this group, including types commonly associated with respiratory disease in man, are capable of producing malignant tumors in young hamsters and a few types have been shown to be oncogenic in young rat. Previous report involving effect of caffein on transformation induced by Adenovirus type 12 [9] has been carried out. The present report represents a continuation of previous study. To obtain evidence concerning the effect of MNNG (N-methyl-N'-nitro-N-nitroguanidine) on transformation, investigation of adenovirus type 12 of this group was undertaken. For practical consideration it was desirable to investigate the effect of MNNG on the adenovirus type 12 induced transformation in L cell. Results were as following 1. Adeno virus type 12 induced transformation was enhanced in the presence of MNNG. 2. Yields of adeno type 12 virus in L cell were slightly inhibited by treatment of MNNG.

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