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Equilibrium, kinetics, and mechanism of the malonic acid–iodine reaction

✍ Scribed by Kenneth R. Leopold; Albert Haim

Publisher
John Wiley and Sons
Year
1977
Tongue
English
Weight
615 KB
Volume
9
Category
Article
ISSN
0538-8066

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✦ Synopsis

The equilibrium constant for the reaction CH,(COOH), + I J -@ CHI(CO0H)Z + 21-+ H+, measured spectrophotometrically at 25OC and ionic strength 1.00M (NaC104), is (2.79 f 0.48) X 10-'M2. Stopped-flow kinetic measurements a t 25OC and ionic strength 1.OOM with [H+] = (2.09-95.0) X lO-3M and [I-] = (1.23-26.1) X l O -3 N indicate that the rate of the forward reaction is given by (kl[12] + k3[13-]) [HOOCCHzCOO-]

The values of the rate constants kl-kg are (1.21 f 0.31) X lo2, (2.41 f 0.15) X lo1, (1.16 f 0.33) X lo1, (8.7 f 4.5) X 10-lM-l-sec-l, and (3.20 f 0.56) X 10IM-2.sec-1, respectively. The rate of enolization of malonic wid, measured by the bromine scavenging technique, is given by k.,[CHz(COOH)2], with ken = 2.0 X An intramolecular mechanism, featuring a sixmember cyclic transition state, is postulated to account for the results on the enolization of malonic acid. The reactions of the enol, enolate ion, and protonated enol with iodine and/or triodide ion are proposed to account for the various rate terms.

  • 1.0 X 10- [CH,(COOH),].

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