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Kinetics and mechanism for oxime formation from benzoylformic acid: Electrostatic interactions in the dehydration of carbinolamines

✍ Scribed by A. Malpica; M. Calzadilla; I. Mejias

Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
140 KB
Volume
40
Category
Article
ISSN
0538-8066

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✦ Synopsis

Abstract

The evidence establishes that oxime formation from benzoylformic acid in the pH range from 0.25 to 5.5 occurs with acid‐catalyzed dehydration of carbinolamines derived from the acid and its anion. The pH‐rate profile shows in order of decreasing pH in two regions: (1) In the pH range from 5.5 to ∼2.2 the second‐order rate constants are linearly dependent on the concentration of hydronium ion and (2) from pH ∼2.2 to 0.25 the rate constants deviate slightly from the line of slope = −1. This slight deviation is a consequence of the very similar values of limiting rate constants of the two forms of the substrate. Electrostatic interactions between charged carbinolamines and hydronium ions are analyzed. © 2008 Wiley Periodicals, Inc. Int J Chem Kinet 40: 554–558, 2008

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