• Journal of the Korean Chemical Society
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• v.62 no.3
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• pp.187-190
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• 2018

A three-component coupling reaction of phenylacetylene, p-toluenesulfonyl azide, and water through copper catalysis is described to provide knowledge of spectroscopy and catalytic reactions and to introduce current research topics in organic chemistry for second-year undergraduate students. In the presence of stoichiometric amounts of phenylacetylene, p-toluenesulfonyl azide, and triethylamine, the reaction was performed with 4 mol% CuCl in water as the sole solvent and was completed in 1.5 h. A practical purification method and recrystallization of the crude reaction mixture resulted in the rapid isolation of the desired product with yields of 42~65%. Students characterized 4-methyl-N-(phenylacetyl)benzenesulfonamide by using melting-point determination, infrared spectroscopy, and nuclear magnetic resonance (NMR) spectroscopy. This experimental procedure and spectroscopic data analysis will serve as a platform for students to apply classroom knowledge in practical state-of-the-art research.

• Journal of the Korean Chemical Society
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• v.41 no.9
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• pp.465-470
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• 1997

A chiral pentadentate ligand, 1,9-bis(S)-prolyl-1,9-dioxo-2,5,8-triaza-nonane, (S,S-prochen) which shows the stereospecific reaction was synthesized from the reaction of S-proline and diethylenetriamine (dien). The red-violet $[Co(SS-prodien)H_2O]ClO_4$ was prepared by the oxidation of the aqueous solution dissolving $CoCl_2{\cdot}6H_2O$ and S,S-prodien. Elemental analysis, electronic absorption spectroscopy, and $^{13}C-NMR$ spectroscopy suggest that the geometrical structure of the Co(III) complex to be an ${\alpha}{\beta}$ (ffm) form, where the dien moiety of the ligand chelates the metal center to comprise a facial isomer, and an aqua ligand coordinates a cis site to the secondary nitrogens of the dien. Based upon the CD spectroscopic analysis, it seems that the absolute configuration of the ${\alpha}{\beta}$(ffm)-$[Co(SS-prodien)H_2O]ClO_4$ has the ${\Lambda}$-form.

• The Korean Journal of Food And Nutrition
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• v.27 no.3
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• pp.532-537
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• 2014

Cortex Phellodendri (CP) is derived from the dried bark of Phellodendron amurense. It has been widely used as a drug in traditional Korea medicine for treating diarrhea, jaundice, swelling pains in the knees and feet, urinary tract infections, and infections of the body surface. Many analytical methods have been used to study oriental herbal medicines, such as thin-layer chromatography, column liquid chromatography, and high performance liquid chromatography (HPLC). In this study, preparative centrifugal partition chromatography (CPC) was successfully carried out in order to separate pure compounds from a CP methanol extract. The optimum two-phase CPC solvent system was composed of n-butanol: acetic acid: water (4:1:5 v/v/v). The flow rate of the mobile phase was 3 mL/min in ascending mode with rotation at 1,000 rpm. The CPC-separated fraction and purification procedures were carried out by preparatory HPLC. The $^1H$ NMR spectrum revealed that the resonances at ${\delta}$ 4.10 and 4.20 ppm corresponded to three protons ($-OCH_3$), whereas those at ${\delta}$ 6.10 ppm corresponded to two protons ($-OCH_2O-$). Further, two aromatic protons (H-11 and H-12) conveys a doublet-doublet pattern. The H-11 doublet and H-12 doublet appear at ${\delta}$ 7.98 and 8.11, respectively. The $^{13}C$ NMR. spectrum showed a tetrasubstituted with a methylenedioxy group at C2 and C3, and two methoxy groups at C9 and C10. The chemical structure of the berberine was identified by $^1H$, $^{13}C$-nuclear magnetic resonance and electrospray ionization-mass spectroscopy spectral data analysis.

• Applied Chemistry for Engineering
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• v.8 no.3
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• pp.425-429
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• 1997

Polyisobutenylsuccinic anhydride(PIBSA), an intermediate for the lubricating oil additive, was prepared by the reaction of polyisobutylene(PIB) with maleic anhydride (MA). The functionality, which indicates the extent of reaction of PIB-a and MA, was determined in the various reaction conditions : fuctionality was 0.98 under the reaction conditions of no solvent for 12 hours at $190^{\circ}C$, 0.21 in benzyl alcohol solvent for 12 hours at $190^{\circ}C$, and 0.03~0.20 with various Lewis acids such as $AlCl_3$, $SnCl_4$, $Et_2AlCl$, and $TiCl_4$. The fuctionality also depended on the structure of PIBs. As ${\alpha}$-olefin content (exo-form) in PIB increased, the fuctionality had a higher value. The structure of PIBSA prepared from PIB and MA was determined with FT IR and $^1H$ NMR spectroscopy. Two strong anhydride IR bands at 1782 and $1855cm^{-1}$ were obserbed and two IR bands at 1639 and $897cm^{-1}$ for unsaturated groups of PIB disappeared. The presence of the anhydride was difficult to find by $^1H$ NMR spectroscopy because the anhydride protons gave relatively small peaks over a 2.0~3.0 range. Polyisobutenylsccinimide (PIBSI), a lublicating oil additive, was prepared by the reaction of PIBSA with diaminoethane.

• Journal of the Korean Wood Science and Technology
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• v.37 no.1
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• pp.73-77
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• 2009

This study was carried out to investigate the valuable antioxidative compound from extracts of Alnus hirsuta Turcz. which has a nationwide distribution. The bark (2 kg) was extracted with 70% aqueous acetone and fractionated, and the ethyl acetate and $H_2O$ fractions, separately, were chromatographed on a Sephadex LH-20 column to purify the mixture and to give two diarylheptanoid compounds. The isolated compounds were analyzed by NMR spectroscopy, including $^1H$, $^{13}C$ and two-dimensional NMR, and identified as oregonin (1) and 1,7-bis-(3,4-dihydroxyphenyl)-heptane-5-O-${\beta}$-D-xylopyranoside (2). The antioxidative activity was evaluated by DPPH method using two diarylheptanoids and acid-hydrolyzed oregonin derivative which indicated higher activity potential. Of those the acid-hydrolyzed oregonin derivative showed highly active potential with the value of 2.6 of $IC_{50}$.

• Bulletin of the Korean Chemical Society
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• v.31 no.5
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• pp.1219-1222
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• 2010

A simple and efficient method has been developed for conversion of arenecarbaldehyde-3-methylquinoxalin-2-ylhydrazones to 3-(2-methylquinoxalin-3-yl)-2-(substitutedphenyl)thiazolidin-4-ones in good yields using microwave irradiation technique on silica as solid support under solvent free conditions. The synthesized compounds were characterized by elemental microanalysis, infrared spectroscopy, $^1H$ NMR, and mass spectroscopy. All the synthesized thiazolidinones were investigated for their antimicrobial and antifungal activities. The results of the biological activities revealed that the compounds 3b, 3d, 3f and 3h exhibited excellent antibacterial activities while 3d and 3h exhibited good antifungal activity.

• Journal of the Korean Magnetic Resonance Society
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• v.21 no.4
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• pp.119-125
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• 2017

The plucking season of green tea leaves is one of the important parameters that decide their metabolic diversity, quality, and prices. The effects of plucking sghlwleasons on green tea metabolites were investigated through metabolite profiling by $^1H$ NMR spectroscopy. The orthogonal projection on latent structure-discriminant analysis (OPLS-DA) showed clear discriminations of green teas by three different grades depending on plucking seasons: Ujeon, Sejak, and Jungjak. These results suggested that the nine peak groups could be used for diagnostics for identification of high quality Ujeon grade of green tea.

• Journal of the Korean Magnetic Resonance Society
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• v.14 no.2
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• pp.127-133
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• 2010

Redox-dependent conformational change of human 8-kDa Dynein light chain (LC8) plays important role in regulating NF-${\kappa}B$ signaling pathway. In this study we characterized the structural states of the oxidized and reduced forms of LC8 by using NMR spectroscopy. The $^1H-^{15}N$ 2D HSQC spectra of oxidized LC8 indicated that no significant change in tertiary structure of LC8 occurred upon oxidation. The chemical shift perturbations of LC8 upon oxidation suggest a redox-dependent quaternary structural change.

• Bulletin of the Korean Chemical Society
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• v.18 no.10
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• pp.1094-1099
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• 1997

The rotational barriers of thioacetamide (TA) and acetamide (AA) were studied using the ab-initio molecular orbital theory and NMR spectroscopy. The calculated rotational barriers using MP2/6-31G**//MP2/6-31G** for TA was 72.26 kJ/mol and 58.19 kJ/mol for AA, respectively. These results are good agreement with the experimental data. The tendency for the change of structural parameters is consistent with the result of formamide. In both amides, the rotational barrier arises from the pyramidalization of nitrogen. The chemical shifts of both amides are shifted upfield when temperature is raised, which confirms pyramidalization of nitrogen. The lineshape of 1H-NMR spectra of TA shows quintet which is contributed from two triplet spectra. This means that the distribution of electrons around the nitrogen is rather symmetric. Ab-initio calculations of electric field gradient for both amides confirm the above results. The above experimental results are well understood by Keith's view on thioamides, which excludes the contribution of resonance structure and considers the origin of rotational barrier to be the same in both thioamides and in corresponding amides.

• Journal of the Korean Magnetic Resonance Society
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• v.22 no.4
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• pp.132-138
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• 2018

The plucking season of green tea leaves is one of the important parameters that decide their metabolic quality. Here, we performed the identification and quantity analysis of the metabolites of the green tea using NMR spectroscopy. We assigned the $^1H$ resonances for sixteen metabolites. This analysis found that four metabolites, gallic acid, quinic acid, theobromine and ECG, exhibited clear discrimination of green teas by the three different grades, Ujeon, Sejak and Jungjak. Our results suggest that these four metabolites could be used for diagnostics for quality control of green tea.