The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Silica sol assisted chromatographic NMR spectroscopy for resolution of trans- and cis-isomers》. Authors are Yang, Ying; Wu, Rui; Huang, Shaohua; Bai, Zhengwu.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).SDS of cas: 610-09-3. Through the article, more information about this compound (cas:610-09-3) is conveyed.
Chromatog. NMR spectroscopy can seperate the mixtures of species with significantly different mol. size, but generally fails for isomeric species. Herein, we reported the resolution of trans- and cis-isomers and their structural analog, which are different in mol. shapes, but similar in mass, were greatly enhanced in the presence of silica soluble The mixtures of maleic acid, fumaric acid and succinic acid, and the mixtures of trans- and cis-1,2-cyclohexanedicarboxylic acids, were distinguished by virtue of their different degrees of interaction with silica soluble Moreover, we found mixed solvents could improve the spectral resolution of DOSY spectra of mixtures
In addition to the literature in the link below, there is a lot of literature about this compound(cis-Cyclohexane-1,2-dicarboxylic acid)SDS of cas: 610-09-3, illustrating the importance and wide applicability of this compound(610-09-3).
Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics