Substrate Specificity in the Cyclodextrin-catalyzed Cleavage of Organic Phosphates and Monothiophosphates in Alkaline Solutions

Publisher Website
Google Scholar
Abstract
Cyclodextrin accelerates the phenol release from organic phosphates such as dialkyl 4-nitrophenyl phosphates, but it decelerates the reactions of the corresponding monothiophosphates in alkaline solutions. Each reaction proceeds via the prior formation of a cyclodextrin–substrate inclusion complex, followed by the nucleophilic attack of the cyclodextrin alkoxide ion or the hydroxide ion on the reaction site of the included substrate. The equilibrium and kinetic parameters involved in the reaction processes were determined and discussed in connection with the geometry of a cyclodextrin–substrate complex.