Rate-controlling step of oxazolinone formation. Secondary and solvent kinetic isotope effects

MS Matta, ME Andracki

Index: Matta, Michael S.; Andracki, Mark E. Journal of the American Chemical Society, 1985 , vol. 107, # 21 p. 6036 - 6039

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Citation Number: 4

Abstract

Abstract: The p-deuterium secondary kinetic isotope effect for the formation of 2- phenyloxazolin-Sone in the alkaline hydrolysis of p-nitrophenyl N-benzoylglycinate (p- N02C6H402CCL2NHOCc6H5, L= H or D) was determined to be kH/kD= 1.03 f 0.02 at temperatures between 10.5 and 40.0" C; activation parameters for the protium ester are AH*= 21.7 f 0.4 kcal mol-'and AS* 298= 31.9 0.6 cal deg-'mol-'. These results, combined ...