The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《FT-IR and FT-Raman spectroscopy study of the cyclic anhydride intermediates for the esterification of cellulose. Part 3. Cyclic anhydrides formed by the isomers of cyclohexanedicarboxylic acid》. Authors are Yang, Charles Q.; Zhang, Guobao.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 In Synthesis of cis-Cyclohexane-1,2-dicarboxylic acid. Through the article, more information about this compound (cas:610-09-3) is conveyed.
Multifunctional carboxylic acids were used as crosslinking agents for cotton and wood pulp cellulose. In the authors’ previous research, the authors found that a polycarboxylic acid esterifies cellulose through the formation of a 5-membered cyclic anhydride intermediate by the dehydration of 2 carboxyl groups. The authors studied the formation of those cyclic anhydride intermediates by different isomers of cyclohexanedicarboxylic acid (CHA) so that the authors can elucidate the effects of mol. structure on the formation of the anhydride intermediates. The authors found that both cis- and trans-1,2-CHA form 5-membered anhydride intermediates when temperature reaches their m.p. and that cis-1,2-CHA forms the cyclic anhydride at temperatures lower than does trans-1,2-CHA. 1,3-CHA forms 6-membered cyclic anhydride at temperatures much higher than its m.p. The formation of a 5-membered cyclic anhydride intermediates takes place at temperatures lower than that of a 6-membered anhydride. This is probably the main reason why those polycarboxylic acids with their carboxylic acid groups bonded to the adjacent carbons of the mol. backbones are more effective crosslinking agents for cellulose than those with their carboxylic groups bonded to the alternative carbons. No formation of cyclic anhydride was found for 1,4-CHA. The formation of a 5-membered cyclic anhydride was accelerated by monosodium phosphate, which is used as a catalyst for the esterification of cotton cellulose by polycarboxylic acids.
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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics