The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Conformation and reactivity. I. Kinetics of the alkaline hydrolysis of the methyl cyclohexanemono- and -dicarboxylate and 4-tert-butylcyclohexanecarboxylates》. Authors are Cavell, E. A. S.; Chapman, N. B.; Johnson, M. D..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).Category: benzisoxazole. Through the article, more information about this compound (cas:610-09-3) is conveyed.
The preparation of pure cis- and trans-4-tert-butylcyclohexanecarboxylic acid and their Me esters was described. Heats and entropies of activation for the alk. hydrolysis of these esters in 1:1 dioxane-H2O, of Me cyclohexanecarboxylate in 1:1 and 1:3 dioxane-H2O, and of all the Me H and di-Me cyclohexanedicarboxylates in 1:3 dioxane-H2O were determined by the methods of Frost and Schwemer (CA 46, 6474h) and of Widequist (CA 46, 9954c) where necessary. Since Me trans-4-tert-butylcyclohexanecarboxylate adopted the diequatorial conformation exclusively, the reactivity in hydrolysis of an equatorial methoxycarbonyl group was characterized, also, with less certainty, that of an axial group, which was hydrolyzed at least 17 times more slowly at 30°. The methoxycarbonyl group was apparently more stable in the equatorial than in the axial conformation. The conformations of the various Me H and di-Me cyclohexanedicarboxylates were discussed in the light of the kinetics of their hydrolyses, and conformational, electrostatic, and primary steric effects in the hydrolyses were elucidated.
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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics