Journal of the Chemical Society. Perkin transactions II p. 373 - 379 (1980)
Update date:2022-08-05
Topics:
Lazarus, Robert A.
Benkovic, Patricia A.
Benkovic, Stephen J.
Intramolecular displacement reactions at phosphorus have been examined in a series of N-alkyl-O-arylphosphorylethanolamines in water at 35 deg C.The examination of the pH-rate profiles and the direct observation by 31P n.m.r. of the reaction products implicate a nucleophilic role for the amine.A rate enhancement of 1E6-1E7 is observed.Structure-reactivity correlations derived by changing the pKa of the amine and leaving group yield values for βnuc<*> 0.7 and βlg<*> -1.25 and support an uncoupled concerted mechanism.A discussion of the mechanisms of nucleophilic reactions involving amines and oxyanions with inter- and intra-molecular phosphate di- and tri-esters is presented.
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