PMID: 1195105Nov 1, 1975Paper

Solvolytic reactions of cyclic anhydrides in anhydrous acetic acid

Journal of Pharmaceutical Sciences
M J HaddadinV Stella

Abstract

The reversible reactions of several cyclic anhydrides with acetic acid to form acetic anhydride and the corresponding dicarboxylic acid, catalyzed by perchloric acid at 25degree, were studied. The equilibrium constants, calculated from spectral data, were 4.85 X 10-4, 1.08 X 10-1, and 4.6 X 10-1 M for succinic, trans-1,2-cyclohexanedicarboxylic, and glutaric anhydrides, respectively. Maleic, phthalic, and cis-1,2-cyclohexanedicarboxylic anhydrides did not undergo any detectable reaction with acetic acid under these conditions, suggesting still higher stability. The reverse rate constants were found to be relatively independent of the structure of the attacking diacid, while the forward rate constants were found to parrallel the equilibrium constants. The rate-determining step for the forward reaction appears to be the breakdown of the tetrahedral intermediate formed by the attack of an acetic acid molecule on the protonated cyclic anhydride.

Citations

Jul 31, 2019·Chemical Communications : Chem Comm·Taeyang AnYan Lee
Oct 28, 2006·Journal of Natural Products·Muhammad Iqbal Choudhary Atta-ur-Rahman
Aug 20, 2004·Journal of Medicinal Chemistry·Aberra FuraW Griffith Humphreys
Jun 15, 2007·Journal of Natural Products·Didier BuissonGuy Lewin
Jan 5, 2001·Journal of Natural Products·K Y Orabi
Apr 11, 2000·Journal of Natural Products·K Y OrabiC D Hufford
Mar 28, 2006·Journal of Natural Products·Shuvendu Das, John P N Rosazza
Jul 30, 1999·Journal of Natural Products·K Y OrabiC D Hufford

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