Intra- and inter-molecular hydron abstraction from allylic carbocation intermediates in aqueous solvent. Observation of a substantial deuterium isotope effect for 1,4-elimination of acetic acid from one of the ion-pair intermediates

1986 ◽  
pp. 321 ◽  
Author(s):  
Alf Thibblin
Keyword(s):  
Acetic Acid ◽  
Isotope Effect ◽  
Ion Pair ◽  
Deuterium Isotope Effect ◽  
Aqueous Solvent

Studies on the Decomposition of Tetra-alkylammonium Salts in Solution. IV. The α-Deuterium Secondary Isotope Effect

1971 ◽  
Vol 49 (1) ◽  
pp. 129-132 ◽  
Author(s):  
E. C. F. Ko ◽  
K. T. Leffek
Keyword(s):  
Isotope Effect ◽  
Ion Pair ◽  
Deuterium Isotope Effect ◽  
Solvent Interaction ◽  
Temperature Range ◽  
Carbonium Ion ◽  
Alkylammonium Salts ◽  
Rate Ratios

The secondary deuterium isotope effect is reported for the decomposition of benzyl-α-d2-phenyldimethylammonium bromide in both chloroform and acetone solvent, over a temperature range of 25 to 30°. The magnitudes of the rate ratios are compared to literature values for SN1 reactions, from which it is concluded that the mechanism of the decomposition involves a carbonium ion or ion-pair. The variation of the isotope effect with solvent is rationalized in terms of specific solvent interaction with the benzyl group.

Partial kinetic ‘resolution’ resulting from a deuterium isotope effect

1991 ◽  
Vol 0 (12) ◽  
pp. 801-802 ◽  
Author(s):  
Panayiotis Anastasis ◽  
Raymond Duffin ◽  
Christopher Gilmore ◽  
Karl Overton
Keyword(s):  
Isotope Effect ◽  
Kinetic Resolution ◽  
Deuterium Isotope Effect
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