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A Novel Reaction of Some Enolisable Ketones not involving the Rate-determining Enolisation Step. Kinetics of the Reaction of Ketones with Trichloroisocyanuric Acid in the Presence of Added Chloride Ion in Acid Medium

DOI: 10.1039/P29870000517

Source and publish data:

Journal of the Chemical Society. Perkin transactions II p. 517 - 522 (1987)

Update date:2022-08-11

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Authors:

Radhakrishnamurti, Patapati SubuRadhakrishnamurti, Patapati Subu

Rath, Nabeen KumarRath, Nabeen Kumar

Panda, Rama KrushnaPanda, Rama Krushna

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Article abstract of DOI:10.1039/P29870000517

Kinetics of the reaction between some enolisable ketones (S) and trichloroisocyanuric acid (TCICA) in aqueous acid-acetic acid medium at 35 deg C follow pseudo-zero-order and pseudo-first-order disappearance of 0 in the absence and the presence of added Cl-, respectively.The rate constants for the latter system exhibit a linear dependence each on 0 and +>, and an increasing and limiting dependence on added ->.The results are interpreted in terms of probable mechanisms involving (i) rate-determining enol formation from the conjugate acid of the ketone (SH+) in the absence of added Cl- and (ii) rate-determining interaction of SH+ with the most effective molecular chlorine species produced by the hydrolysis of TCICA (rather than a rate-determining interaction of enol with Cl2) in the presence of added Cl-, prior to the rapid steps of product formation.

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