• Title/Summary/Keyword: Amides

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Effect of Dimethylformamide on Post-Thaw Motility, Acrosome Integrity, and DNA Structure of Frozen Boar Sperm

  • Hwang, You-Jin;Yang, Jae-Hun;Kim, Sang-Ok;Kim, Bo-Kyung;Choi, Seon-Kyu;Park, Choon-Keun;Kim, Dae-Young
    • Journal of Embryo Transfer
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    • v.24 no.4
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    • pp.275-279
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    • 2009
  • The beneficial effect of glycerol as a cryoprotectant, especially for sperm cryopreservation, has been shown in many studies. However, glycerol is toxic to living cells, and boar sperm in particular show greater sensitivity to glycerol than sperm from other domestic animals. Amides have been studied as alternative cryoprotectants for freezing stallion sperm. Sperm frozen in methylformamide or dimethylformamide as cryoprotectants show similar motility when thawed compared with sperm frozen in glycerol. We evaluated the cryoprotective effects of dimethylformamide on boar sperm freezing. To test the effect of amides, the concentration of boar semen was adjusted to $10^9sperm/mL$, and seminal plasma was removed using Hulsen solution. After centrifugation, the pellet was diluted in modified-Modena B extender. Lactose-egg yolk (LEY) extender was used as the cooling extender. The freezing extender was madeed aaddition of the optimal amount of glycerol and amides to LEY-Glycerol-Orvus ES Paste extender, and this extender was used for the second dilution. Diluted sperm were frozen in liquid nitrogen using the 0.5 mL straw method. Sperm frozen in extender with glycerol as a cderol were compared with those frozen in extender including the different amides. Sperm were tested for motility, viability, the sperm chromatin structure assay, and normal apical ridge after thawing. The percent of motile sperm diluted in glycerol was as high as that in the stallion study (61%). Dimethylformamide showed positive effects on sperm quality and was better than glycerol. Methylformamide provided similar sperm quality as glycerol. Therefore, dimethylformamide is useful for reducing cryoinjury in boar sperm and is expected to be useful as an alternative cryoprotectant.

Syntheses of Amide Bonds and Activations of N-C(sp3) Bonds

  • Hong, Jang-Hwan
    • Journal of Integrative Natural Science
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    • v.10 no.4
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    • pp.175-191
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    • 2017
  • In organic chemistry amide synthesis is performed through condensation of a carboxylic acid and an amine with releasing one equivalent of water via the corresponding ammonium carboxylate salt. This method is suffering from tedious processes and poor atom-economy due to the adverse thermodynamics of the equilibrium and the high activation barrier for direct coupling of a carboxylic acid and an amine. Most of the chemical approaches to amides formations have been therefore being developed, they are mainly focused on secondary amides. Direct carbonylations of tertiary amines to amides have been an exotic field unresolved, in particular direct carbonylation of trimethylamine in lack of commercial need has been attracted much interests due to the versatile product of N,N-dimethylacetamide in chemical industries and the activation of robust N-C($sp^3$) bond in tertiary amine academically. This review is focused mainly on carbonylation of trimethylamine as one of the typical tertiary amines by transition metals of cobalt, rhodium, platinum, and palladium including the role of methyl iodide as a promoter, the intermediate formation of acyl iodide, the coordination ability of trimethylamine to transition metal catalysts, and any possibility of CO insertion into the bond of Me-N in trimethylamine. In addition reactions of acyl halides as an activated form of acetic acid with amines are reviewed in brief since acyl iodide is suggested as a critical intermediate in those carbonylations of trimethylamine.

Effect of Some Amides on the Hindered Rotation of N-C(S) Bond of Thioacetamide in $CCl_4$ ($CCl_4$속에서 Thioacetamide의 N-C(S) 부자유회전에 미치는 몇가지 Amide의 영향)

  • Seong-Gu Ro;Young-Sang Choi;Chang-Ju Yoon
    • Journal of the Korean Chemical Society
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    • v.31 no.6
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    • pp.486-490
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    • 1987
  • The effect of the hydrogen-bonding between thioacetamide (TA) and amides (N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMA) and N,N-dimethylpropionamide (DMP)) on the hindered rotation of N-C(S) bond of TA was investigated by the nmr spectroscopy. The $^1H$-nmr spectrum of $NH_2$ group in TA was distinctly separated into two peaks with increasing the amount of $CCl_4$ and the effect of amides on the peak separation was in the order of DMF < DMA < DMP. Those phenomena were interpreted in terms of hydrogen-bonding between TA and amide.

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MO Studies on the Conformational Stabilities and the Rotational Barriers about C-N Bond in Amides (Amide류에서 형태안정화와 C-N결합의 회전장벽에 관한 분자궤도론적 연구)

  • Wang Ki Kim;Chang Kook Sohn;Ikchoon Lee
    • Journal of the Korean Chemical Society
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    • v.32 no.3
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    • pp.163-170
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    • 1988
  • The MNDO calculations were performed on the various rotamers of N-methyl formamide, N,N-dimethyl formamide, N-methyl acetamide, and N,N-dimethylacetamide in order to investigate the contribution of the one-electron and the steric effect on their rotational barriers about the C-N bond. Results show that while the conformational stabilities of formamides depend mainly on the one-electron factor, those of acetamides depend mainly on the steric factor. According to results obtained by calculations on the rotational barriers about C-N bond, for N-monosubstituted amides the steric effect is larger in the rotational ground state than in the transition state and for N,N-disubstituted amides the steric effect is larger in the rotational transition state.

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Synthesis of Vegetable-based Alkanol Amides for Improving Lubricating Properties of Diesel Fuel (경유의 윤활 성능 향상을 위한 식물유 기반 알칸올 아마이드의 합성)

  • Yuk, Jung-Suk;Kim, Young-Wun;Yoo, Seung-Hyun;Chung, Keun-Wo;Kim, Nam-Kyun;Lim, Dae-Jae
    • Applied Chemistry for Engineering
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    • v.23 no.4
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    • pp.421-427
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    • 2012
  • To improve the lubricity of ultra low sulfur diesel, vegetable oil-based alkanol amide derivatives were prepared and their lubricity properties were studied. To synthesize the alkanol amides, we conducted the amidation reaction of diethaolamine High Frequency Reciprocating Rig (HFRR) and the fatty acid methyl esters, obtained by the continuous transesterification of methanol and several vegetable oil, such as soybean oil, palm oil and coconut oil. The synthesized amides were soluble in ultra low sulfur diesel in the concentration range of ca. 1 wt%; the lubricating properties of ultra low sulfur diesel containing 120 ppm of amides were measured using an HFRR method. It was found that the wear scar diameter in the pure ultra low sulfur diesel decreased significantly from 581 ${\mu}m$ to 305~323 ${\mu}m$ upon the addition of the amides, indicating that lubricating properties of the diesel were improved. On the other hand, the types of vegetable oils did not affect the wear scar diameters, implying that lubricating properties of the diesel did not depend strongly on the structures of alkyl groups of alkanol amide derivatives. When we measured the lubricating properties of the one type of diesels containing various amounts of alkanol amide, we observed that the wear scar diameter decreased drastically with increasing the amide concentration, meaning that the lubricity improved with the amide concentration.