thioamide
Sign in to saveAlso known as thioamides, thionamide, thiourylene
thumb|right|150px|class=skin-invert-image|General structure of a thioamide A thioamide (rarely, thionamide, but also known as thiourylenes) is a functional group with the general structure , where are any groups (typically organyl groups or hydrogen). Analogous to amides, thioamides exhibit greater multiple bond character along the C-N bond, resulting in a larger rotational barrier.
Research
3,549 papers- Ynamide-Mediated Thioamide and Primary Thioamide Syntheses.The Journal of organic chemistry · 2022
- Thioamide Analogues of MHC I Antigen Peptides.Journal of the American Chemical Society · 2023
- Thioamide-based fluorescent sensors for dipeptidyl peptidase 4.Chemical communications (Cambridge, England) · 2024
- Backbone thioamide directed macrocyclisation: lactam stapling of peptides.Organic & biomolecular chemistry · 2022
- Construction of Thioamide Peptides from Chiral Amino Acids.Angewandte Chemie (International ed. in English) · 2023
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7 sectionsContents
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- In biochemistry and medicine
- Related compounds
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thumb|right|150px|class=skin-invert-image|General structure of a thioamide A thioamide (rarely, thionamide, but also known as thiourylenes) is a functional group with the general structure {{chem2|R^{1}\sC(\dS)\sNR^{2}R^{3}|}}, where {{chem2|R^{1}, R^{2} and R^{3}|}} are any groups (typically organyl groups or hydrogen). Analogous to amides, thioamides exhibit greater multiple bond character along the C-N bond, resulting in a larger rotational barrier.
==Synthesis== Thioamides are typically prepared by treating amides with phosphorus pentasulfide, a reaction first described in the 1870s. An alternative to P2S5 is its more soluble analogue Lawesson's reagent. These transformations can be seen in the synthesis of tolrestat. 700px