The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《The configuration of polymethylenedicarboxylic acids. I. The dissociation constants of the cyclohexanedicarboxylic acids》. Authors are Kuhn, Richard; Wassermann, Albert.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).HPLC of Formula: 610-09-3. Through the article, more information about this compound (cas:610-09-3) is conveyed.
The 1st and 2nd dissociation constants for the cyclohexanedicarboxylic acids in water and in 50% MeOH are given as follows (-log K, -log K2 and K1/K2, resp.): In H2O: o-cis, 4.34 (19°), 6.76 (19°), 267; o-trans, 4.18 (18°), 5.93 (19°), 56; m-cis, 4.10 (16°), 5.46 (16°), 23; m-trans, 4.31 (19°), 5.73 (19°), 26; p-cis, 4.44 (20°), 5.79 (19°), 22; p-trans, 4.18 (16°), 5.42 (19°), 17. In 50% MeOH: o-cis, 5.26 (18°), 8.20 (18°), 885; o-trans, 5.38 (18°), 7.31 (18°), 85; m-cis, 5.25 (17°), 6.83 (17°), 38; m-trans, 5.48 (19°), 7.40 (19°), 83; p-cis, 5.59 (19°), 7.15 (19°), 36; p-trans, 5.32 (18°), 6.81 18°), 30. The configurations of the various isomeric forms of the hexahydrophthalic acids are graphically presented.
Although many compounds look similar to this compound(610-09-3)HPLC of Formula: 610-09-3, numerous studies have shown that this compound(SMILES:O=C([C@H]1[C@@H](C(O)=O)CCCC1)O), has unique advantages. If you want to know more about similar compounds, you can read my other articles.
Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics