Catalysis of Hydrogen-Deuterium Exchange Reactions by 4-Substituted Proline Derivatives.

ABSTRACT: The identification and understanding of structure-activity relationships is vital for rational catalyst design. A kinetic study of the hydrogen-deuterium exchange reaction of cyclohexanone in aqueous solution, as catalyzed by proline derivatives, has revealed valuable structure-activity relationships. In phosphate-buffered solution, cis-4-fluoroproline is more active than the trans isomer, a distinction that appears to originate from a destabilizing interaction between the fluorine atom and phosphate anion during general acid-catalyzed dehydration of the carbinolamine intermediate. trans-4-Ammoniumprolines are exceptionally active catalysts owing to favorable Coulombic interactions involving the ammonium group and the alkoxide moiety formed upon 1,2-addition of the proline derivative to th

SUBMITTER: Myers EL 

PROVIDER: S-EPMC6486814 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature