Comparative kinetic studies on the alkaline hydrolysis of halogen substituted isocoumarins

Authors

HAFIZ BADARUDDIN AHMAD
MUHAMMAD ASLAM MALANA
MUHAMMAD YOUSAF
MUHAMMAD REHAN
MAZHAR ABBAS

DOI

10.3906/kim-0906-75

Abstract

Kinetics of the hydrolysis of 3-(2'-chloro-6'-fluorobenzyl) isocoumarin (1), 3-(4'-fluorophenyl)isocoumarin (3), 3-(2'- fluorophenyl)isocoumarin (5), 3-(2'-chlorophenyl)isocoumarin (7), and 3-(4'-chlorophenyl)isocoumarin (9) were studied spectrophotometrically in the presence of aqueous solution of potassium hydroxide. The rates of hydrolyses for these isocoumarins were compared. The data for isocoumarin (1) were further investigated to probe the reaction mechanism. The dependence of pseudo-first order rate constant k_{obs} on hydroxide ion concentration is fitted by the expression k_{obs} = k_o + k_1[OH] + k_2 [OH]^2, showing the formation of monoanionic and dianionic tetrahedral intermediates during the course of reaction. The magnitude of k_o shows significant participation of solvent in the reaction mechanism.

Keywords

Hydrolysis, isocoumarin, kinetics.

First Page

381

Last Page

386

Recommended Citation

AHMAD, HAFIZ BADARUDDIN; MALANA, MUHAMMAD ASLAM; YOUSAF, MUHAMMAD; REHAN, MUHAMMAD; and ABBAS, MAZHAR (2010) "Comparative kinetic studies on the alkaline hydrolysis of halogen substituted isocoumarins," Turkish Journal of Chemistry: Vol. 34: No. 3, Article 7. https://doi.org/10.3906/kim-0906-75
Available at: https://journals.tubitak.gov.tr/chem/vol34/iss3/7