Author(s)

Ikumi Otomo, Chiaki Kuroda^*

Department of Chemistry, Rikkyo University, Tokyo, Japan.

Amphipathic-type thioesters CH₃(CH₂)_mCOS(CH₂)_nCOONa (m + n = 12) were synthesized and their reaction with various alkylamines was examined. Compounds having thioester moiety close to carboxylate (m = 10, n = 2) afforded the corresponding amides in good yields, while the substrate having thioester moiety distant from carboxylate (m = 2, n = 10) afforded the amides in relatively low yield. In all cases, the difference in yield due to the chain length of amine was not observed. The results indicated that the reaction took place effectively near the surface of micelle. However, the reaction was found to occur not only on micelle surface but also in solution.

Hydrophobic Effect, Amides, Thioesters

Otomo, I. and Kuroda, C. (2015) Effect of the Position of Reaction-Site in Amphipathic-Type Thioester in Aqueous Amidation Reaction. Advances in Chemical Engineering and Science, 5, 311-316. doi: 10.4236/aces.2015.53032.