Catalysis of the enolization of acetone by mono-and dicarboxylate bases. The role of hydrogen bonding
S Venimadhavan, KP Shelly…
Index: Venimadhavan, S.; Shelly, Kevin P.; Stewart, Ross Journal of Organic Chemistry, 1989 , vol. 54, # 10 p. 2483 - 2485
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Citation Number: 8
Abstract
The enolization of acetone catalyzed by a series of aliphatic carboxylate bases (eq 1) was studied by Bell and Lidwell,'who reported a Bransted exponent@ of 0.88 for the four bases that comprised the series. As a part of a study of steric and other effects in proton-transfer reactions, 2 we have reexamined and greatly extended their series and have included in it a considerable number of dicarboxylic acid dianions.
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