Rate of enolate formation is not very sensitive to the hydrogen bonding ability of donors to carboxyl oxygen lone pair acceptors; a ramification of the principle of non- …

…, TS Snowden, MD Best, EV Anslyn

Index: Zhong, Zhenlin; Snowden, Timothy S.; Best, Michael D.; Anslyn, Eric V. Journal of the American Chemical Society, 2004 , vol. 126, # 11 p. 3488 - 3495

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Citation Number: 24

Abstract

Two series of structures (1 and 2) possessing intramolecular hydrogen bonds to the lone- pair electrons of carbonyl oxygens have been examined to reveal the influence of the p K a of the hydrogen-bond donor on the rate of general-base-catalyzed enolate formation. The geometry of the hydrogen bonds is well accepted to be appropriate for intramolecular hydrogen-bond formation. Yet, as revealed by Brønsted plots, both series show very little ...