OXIBASE SCALE AND DISPLACEMENT REACTIONS .17. REACTION OF NUCLEOPHILES WITH ETHYL TOSYLATE AND EXTENSION OF OXIBASE SCALE

The rate constants of ten nucleophiles reacting with ethyl tosylate have been measured in aqueous solution. From these rate constants the oxibase scale parameters for ethyl tosylate have been obtained; α = 1.48 and β = 0.03 at 25° in water. The nucleophilic constants of several nucleophiles have been obtained for the temperature range of 0-100° in water. The uses of the oxibase scale are extended to include the energetics of isotopic exchange reactions as well as the relationship between the oxidation potential and the basicity. © 1969, American Chemical Society. All rights reserved.