The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《The kinetics of the acid-catalyzed hydrolysis of the methyl esters of cyclohexanedicarboxylic acids》. Authors are Smith, Hilton A.; Scrogham, Kenneth G.; Stump, Billy L..The article about the compound:cis-Cyclohexane-1,2-dicarboxylic acidcas:610-09-3,SMILESS:O=C([C@H]1[C@@H](C(O)=O)CCCC1)O).Application of 610-09-3. Through the article, more information about this compound (cas:610-09-3) is conveyed.
Isomeric cyclohexane dicarboxylic acids (I) were made by reduction of phthalic acids: cis-1,2 (II), m. 194°; trans-1,2 (III), m. 227.5-9.4°; cis-1,3 (IV), m. 167.2-8.2°; cis-1,4 (V), m. 170-2°; and trans-1,4 (VI), m. 312-13°. Di-Me esters made by acid-catalyzed esterification with MeOH were: II, b12 124.4°; III, m. 30.2-30.8°; V, b10 131°; and VI, m. 69°. IV di-Me ester, b10 130.6°, was made from the Ag salt and MeI, whereas trans-1,3-di-Me ester (VII), b20 140°, was made from H and 1,3-C6H4(CO2Me)2 with Adams Pt catalyst. Mono-Me derivative of II, m. 68.5-9.0°, was made similarly from 2-HO2CC6H4CO2Me and H. Mono-Me derivative of III, m. 94.5-95°, was made from the acid and MeOH. Mono-Me derivative of IV, m. 66.2-7.0°, was made from the acid chloride and MeOH. By treatment of the di-Me esters with 1 equivalent KOH, mono-Me derivative of V, m. 106.6-8.6°, mono-Me derivative of VI, m. 125.6-6.8°, and mono-Me derivative of trans-1,3-I were prepared Acid-catalyzed rate constants for these esters were determined at 25°, 35°, 45°, and 55° and the heats of activation calculated Me and di-Me esters of II and III hydrolyzed most slowly, those of IV and VI most rapidly, and those of V and VII at an intermediate rate.
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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics