Parallel behavior in kinetic and NMR effects: secondary deuterium isotope effects on the alkaline hydrolysis of esters

MS Matta, DE Broadway, MK Stroot

Index: Matta, Michael S.; Broadway, Dale E.; Stroot, Michele K. Journal of the American Chemical Society, 1987 , vol. 109, # 16 p. 4916 - 4918

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Citation Number: 5

Abstract

Abstract: p-Deuterium secondary kinetic isotope effects (pD KIEs) on the alkaline hydrolysis of the p-nitrophenyl esters of acetic, propanoic, butanoic, and pentanoic acids in pH 10.70, 0.20 M carbonate buffer at 25" C tend to increase with increasing chain length of the esters up to the pentanoate. The pD KIEs are respectively 0.975 f 0.004, 0.960 f 0.002, 0.940 f 0.001, and 0.948 f 0.004. The activation energies of the esterolyses of the isotopically light ...