• Title/Summary/Keyword: Thioamides

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Direct and Efficient Conversion of Tertiary Thioamides to S-2-Oxo Thioesters under Solvent-free Conditions

  • Boeini, Hassan Zali;Khajeh, Aida
    • Bulletin of the Korean Chemical Society
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    • v.32 no.4
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    • pp.1201-1203
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    • 2011

  • A one-pot conversion of tertiary thioamides to S-2-oxo thioesters is reported. Hence, tertiary thioamides were reacted with ${\alpha}$-halo ketones or acids under solvent-free conditions to produce the corresponding oxo-thioesters in good to excellent yields.

  • https://doi.org/10.5012/bkcs.2011.32.4.1201 인용 PDF KSCI

Synthesis of Amide from Thioamide by Treatment of SiO2 or SeO2

  • Jung, Dai-Il;Lee, Jin-A;Lee, Do-Hun;Kwak, Moon-Jung;Lee, Soo-Jin;Park, You-Mi;Park, Soon-Kyu;Kim, Hyun-Sook
    • Journal of Life Science
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    • v.9 no.2
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    • pp.49-51
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    • 1999

  • Reactions of 2,6-Lutidine with active methyl group anilines in the presence of sulfur gave the desired thioamides 1. Reactions of synthesized thioamides 1 with sulfur and SiO2 or SeO2 gave the corresponding amide 2. We now report conversion of thioamide to amide by using oxidzing inorganic reagant

Ab-inito and NMR Studies on the Rotational Barrier for Thioacetamide and Acetamide

  • 최영기;송근일;최영상;윤창주
    • 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.

  • https://doi.org/10.5012/bkcs.1997.18.10.1094 인용 PDF

Hydrogen Bonding between Thioamides and Dimethylsulfoxide (DMSO) in $CCl_4$ ($CCl_4$속에서 Thioamides 와 Dimethyl Sulfoxide (DMSO) 사이의 수소 결합에 대한 연구)

  • Young-Lac Do;Seon-Jin Kim;Chang-Ju Yun;Young-Sang Choi
    • Journal of the Korean Chemical Society
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    • v.36 no.2
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    • pp.185-190
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    • 1992

  • Near-IR spectra for $ν_{\alpha}$+ Amide Ⅱ combination band of thioamides, and very dilute thioamide-DMSO solution in CCl4 were recorded in the temperature range of $5^{\circ}C$ to $55^{\circ}C$. This combination band was resolved by the computer program into two Lorentzian-Gaussian product function which have been identified with monomeric thioamide and thioamide-DMSO 1 : 1 complex. Equilibrium constants and thermodynamic parameters for the thioamide-DMSO hydrogen bonding were elucidated by the analysis of conce ntration and temperature dependent spectra. The hydrogen bonding strength between thioacetamide (TA) and DMSO in $CCl_4$ is stronger than that between thiopropionamide (TPA) and DMSO in CCl4. The ${\Delta}H^{\circ}$ for the TA-DMSO and TPA-DMSO 1 : 1 complex in CCl4 were -15.3 kJ${\cdot}$$mol^{-1}$ and -14.2 kj${\cdot}$$mol^{-1}$, respectively.

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