• Title/Summary/Keyword: Sulfonyl chloride

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The Synthesis of Pyrrolidone-N-sulfonyl Chloride and Its Catalytic Effect in Anionic Polymerization of Pyrrolidone (Pyrrolidone-N-sulfonyl Chloride의 합성 및 Pyrrolidone-N-sulfonyl Chloride / KOH 촉매작용에 의한 Pyrrolidone의 음이온 중합)

  • W.J. Chung;S.K. Choi
    • Journal of the Korean Chemical Society
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    • v.23 no.6
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    • pp.402-411
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    • 1979
  • The synthesis of pyrrolidone-N-sulfonyl chloride has been carried out by the reaction of pyrrolidone with sulfuryl chloride in benzene. It was attempted to study the catalytic effect of pyrroldone-N-sulfonyl chloride as an initiator for anionic polymerization of pyrrolidone. It was found that as a concentration of initiator decreased, inherent viscosity of the resulting polymer increased up to 1.8 dl/g. The highest rate of polymerization and equilibrium conversion was observed when mole ratio of PNSC to KOH was 0.25. In general, the observed value of polymerization and equilibrium conversion in circumstances using PNSC/KOH catalysis system were higher than using $CO_2$/KOH catalysis system.

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Determination of Amine Compounds Using 1-(N,N-Dimethylamino) pyrene-6-sulfonyl chloride as a New Fluorescent Derivatizing Reagent for HPLC (새로운 HPLC용 형광유도체화제인 1-(N,N-dimethylamino) pyrene-6-sulfonyl chloride를 이용한 아민화합물의 분석)

  • 이윤중;김용희;조정길
    • YAKHAK HOEJI
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    • v.35 no.4
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    • pp.288-294
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    • 1991
  • A new fluorescent derivatizing reagent was developed to be used in HPLC for the trace determination of primary and secondary amines. This new reagent, 1-(N,N-dimethylamino)pyrene-6-sulfonyl chloride, was synthesized by the chlorination of sodium 1-(N,N-dimethylamino)pyrene-6-sulfonate which was obtained from 1-(N,N-dimethylamino)pyrene after sulfonation. Ephedrine and norephedrine were derivatized quantitatively by this reagent. The optimum conditions for the derivatization such as pH, reagent concentration, reaction time and reaction temperature ware examined. The structures of derivatives were identified by IR, $^{1}$H-NMR and MS methods. The fluorescence properties and the stability of the derivatives were examined. The derivatives were separated on silica column with an isocratic elution using the mixture of n-hexane and ethylacetate and monitored by fluorescene detector. Linear calibration curves were obtained and detection limits in a 10 $\mu$l injection volume were 5 picomole for ephedrine and norephedrine.

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Nucleophilic Displacement at Sulfur Center (V). EHT Calculations on Sulfonyl Chlorides (황의 친핵치환 반응 (제5보). 각종 Sulfonyl Chloride에 대한 EHT 계산)

  • Lee Ikchoon;Kim, Ui Rak;Bae, Seon Ho
    • Journal of the Korean Chemical Society
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    • v.18 no.3
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    • pp.171-174
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    • 1974
  • The extended Huckel calculations have been conducted on sulfonyl chlorides $ RSO_2Cl,\;R=C6H_5-,\;CH3-,\;OCH3-$. Results are discussed using ground state electronic structures. $S_N$ reactivity has been discussed using calculated reactivity indices. Particularly, which the substitution of chlorine is take placed or not on $ROSO_2Cl$ in which is suggested by Buncel et al., is discussed by means of some basis on the MO theoretical ground.

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Investigation on Chain Transfer Reaction of Benzene Sulfonyl Chloride in Styrene Radical Polymerization

  • Li, Cuiping;Fu, Zhifeng;Shi, Yan
    • Macromolecular Research
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    • v.17 no.8
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    • pp.557-562
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    • 2009
  • The free radical polymerization of styrene was initiated with azobis(isobutyronitrile) in the presence of benzene sulfonyl chloride. Analysis of the terminal structures of the obtained polystyrene with $^1H$ NMR spectroscopy revealed the presence of a phenyl sulfonyl group at the ${\alpha}$-end and a chlorine atom at the ${\omega}$-end of each polystyrene chain. The terminal chlorine atom in the polystyrene chains was further confirmed through atom transfer radical polymerization (ATRP) of styrene and methyl acrylate using the obtained polystyrenes as macroinitiators and CuCl/2,2'-bipyridine as the catalyst system. GPC traces of the products obtained in ATRP at different reaction times were clearly shifted to higher molecular weight direction, indicating that nearly all the macroinitiator chains initiated ATRP of the second monomers. In addition, the number-average molecular weights of the polystyrenes increased directly proportional to the monomer conversions, and agreed well with the theoretical ones.

Reaction Intermediate of Organic Sulfur Compund Ⅱ. Nucleophilic Substitution Reaction of Disulfonyl Chloride Compounds

  • Dae-Dong Sung;Dae-Il Jung;Kyu-Chul Kim;Yang-Hee Kim;Soo-Dong Yoh
    • Bulletin of the Korean Chemical Society
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    • v.11 no.1
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    • pp.65-69
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    • 1990
  • The nucleophilic substitution reactions of naphthalene-1,5-disulfonyl chloride and 4-fluorosulfonylbenzenesulfonyl chloride with p-substituted anilines and methyl substituted pyridines in methanol-acetonitrile mixtures and hydrolyses of those disulfonyl halides have been studied by means of conductometric and polarographic methods. A large difference in the selective parameter, ${\rho}_N$ between mono-sulfonyl chloride and disulfonyl halide can be taken as an evidence that the second $SO_2Cl$ grolup of naphthalene-1,5-disulfonyl chloride also takes part in the reaction in contrast to sulfonyl fluoride in 4-fluorosulfonylbenzenesulfonyl chloride, which only acts as a substituent in the nucleophilic substitution reaction.

Synthesis and Photocharacteristics of Polysiloxane substituted Naphthoquinone-1,2-diazide sulfonyl group (Naphthoquinone-1,2-Diazaide-Sulfonyl기 치환 Polysiloxane의 합성과 그 감광특성)

  • Kang, Doo-Whan;Chung, Nag-Jin
    • Applied Chemistry for Engineering
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    • v.2 no.4
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    • pp.348-355
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    • 1991
  • Polysiloxane copolymers were prepared by copolymerizing hexamethylcyclotrisiloxane with tetramethylcyclotetrasiloxane, and then reacted with allyamine. Copolymers containing naphthoquinone-1,2-diazide-5-sulfonyl group were synthesized by reacting naphthoquinone-1,2-diazide-5-sulfonyl chloride with siloxane copolymers having amino group. Thermal decomposition temperatures of copolymers were $360{\sim}450^{\circ}C$, and photosensitive characteristics were dependent on the molecular weights of backbone resins and sensitizers. Sensitivity of copolymers was $50{\sim}120mJ/cm^2$ and contrast(${\gamma}$) was 1.4~2.1.

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Rate and Product Studies of 5-Dimethylamino-Naphthalene-1-Sulfonyl Chloride under Solvolytic Conditions

  • Koh, Han Joong;Kang, Suk Jin
    • Bulletin of the Korean Chemical Society
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    • v.35 no.8
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    • pp.2285-2289
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    • 2014
  • The solvolysis rate constants of 5-dimethylamino-naphthalene-1-sulfonyl chloride ($(CH_3)_2NC_{10}H_6SO_2Cl$, 1) in 31 different solvents are well correlated with the extended Grunwald-Winstein equation, using the $N_T$ solvent nucleophilicity scale and $Y_{Cl}$ solvent ionizing scale with sensitivity values of $0.96{\pm}0.09$ and $0.53{\pm}0.03$ for l and m, respectively; the correlation coefficient value was 0.955. These l and m values can be considered to support an $S_N2$ reaction pathway having a transition state (TS) structure similar to that of the benzenesulfonyl chloride reaction. This interpretation is further supported by the activation parameters, i.e., relatively small positive ${\Delta}H^{\neq}$ (12.0 to $15.9kcal{\cdot}mol^{-1}$) and large negative ${\Delta}S^{\neq}$ (-23.1 to $-36.3cal{\cdot}mol^{-1}{\cdot}K^{-1}$) values, and the solvent kinetic isotope effects (SKIEs, 1.34 to 1.88). Also, the selectivity values (S = 1.2 to 2.9) obtained in binary solvents are consistent with the proposed mechanism.

Convenient One-Pot Synthesis of Sulfonamides from Thiols and Disulfides Using 1,3-Dichloro-5,5-dimethylhydantoin (DCH)

  • Veisi, Hojat
    • Bulletin of the Korean Chemical Society
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    • v.33 no.2
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    • pp.383-386
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    • 2012
  • A convenient synthesis of sulfonamides from thiols and disulfides is described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with 1,3-dichloro-5,5-dimethylhydantoin (DCH) under Nbenzyl-trimethylammonium chloride and water. The sulfonyl chlorides are then further allowed to react with excess amine in the same reaction vessel.

Studies on the Synthesis of Yellow Coupler and Color Development (황색 발색제의 합성과 발색현상에 관한 연구)

  • Kim, Yeoung-Chan
    • Journal of the Korean Applied Science and Technology
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    • v.29 no.1
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    • pp.116-121
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    • 2012
  • In this paper, yellow coupler was prepared by the reaction of ${\alpha}$-pivaloyl- 2-chloro-5-aminoacetaniline hydrogen chloride with 1-hexadecane sulfonyl chloride in the presence of pyridine. The product was identified by using various analytical tools such as melting poin elemental analyzer, IR spectrophotometer, UV-Vis spectrophotometer, mass spectrometer. The reaction of yellow coupler with CD-3(color development agent) was shown yellow color.

Studies on Photosensitive Polymers (IX). Syntheses of Naphthoquinone-1,2-diazide-5-sulfonyl Esters with Backbone Resins (감광성 수지에 관한 연구 (제 9 보). Naphthoquinone-1,2-diazide-5-sulfonyl Esters의 합성)

  • Shim Jyong Sup;Kang Doo Whan
    • Journal of the Korean Chemical Society
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    • v.19 no.3
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    • pp.198-206
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    • 1975
  • Polymers with photosensitive functional groups, the naphthoquinone-1,2-diazide-5-sulfonyl esters(PGND, BEND and PVAND) of polyglyceryl phthalate(PG), bisphenol A-epichlorohydrin polycondensate(BE) and polyvinyl alcohol(PVA), were prepared. The molecular weights of the starting materials were determined by the cryoscopic method, i.e., in the range of 650${\sim}$1200 for PG and 780${\sim}$1320 for BE, PGND, BEND and PVAND were prepared by esterification of PG, BE and PVA with naphthoquinone-1,2-diazidie-5-sulfonyl chloride, and the replacements of such a functional groups were confirmed by the infrared absorption spectra and elemental analyses. The good agreement between the observed values of elemental analyses (PGND, BEND and PVAND) and the calculated values, indicated that the degree of polymerization did not change in the course of esterification of PG, BE and PVA.

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