Thioamide

A thioamide (rarely, thionamide, but also known as thiourylenes) is a functional group with the general structure R¹−C(=S)−NR²R³, where R¹, R² and R³ 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.^[1]

^ Wiberg, Kenneth B.; Rablen, Paul R. (1995). "Why Does Thioformamide Have a Larger Rotational Barrier Than Formamide?". J. Am. Chem. Soc. 117 (8): 2201–2209. doi:10.1021/ja00113a009.

[1] Wiberg, Kenneth B.; Rablen, Paul R. (1995). "Why Does Thioformamide Have a Larger Rotational Barrier Than Formamide?". J. Am. Chem. Soc. 117 (8): 2201–2209. doi:10.1021/ja00113a009.

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