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
via PubMed
~4 min read
Encyclopedic overview
7 sectionsContents
- Synthesis
- Specialized methods
- Reactions
- Structure
- In biochemistry and medicine
- Related compounds
- References
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
Excerpted from Wikipedia’s “thioamide” article, available under the CC BY-SA 4.0 licence.