Bulletin of the Chemical Society of Japan

Hydrophobic Effect and Substrate Specificity in Reaction of Thioester and Amine in Water

A Torihata, C Kuroda

Index: Torihata, Atsushi; Kuroda, Chiaki Bulletin of the Chemical Society of Japan, 2010 , vol. 83, # 12 p. 1534 - 1538

Full Text: HTML

Citation Number: 2

Abstract

The extent of hydrophobic effect in amidation reaction of alkyl thioester with alkylamine in water was studied. The yield of the products was primarily dependent on the alkyl group of amine. For example, the reaction of S-dodecyl dodecanethioate with dodecylamine proceeded in good yield, while the reaction did not occur with cyclohexylamine, piperidine, and dipropylamine. The effect of chain length of n-alkylamine was studied to suggest the ...