Zwitterion formation and subsequent carboxylate–pyridinium NH synthon generation through isomerization of 2-anilinonicotinic acid
| Autor: | Danrui Xu, Pengyun Yue, Sihui Long, Sean Parkin, Caiqiao Dong, Mingtao Zhang, Tonglei Li, Faquan Yu, Conggang Li |
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| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Hydrogen bond Carboxylic acid Synthon General Chemistry 010402 general chemistry Condensed Matter Physics 01 natural sciences Medicinal chemistry 0104 chemical sciences Turn (biochemistry) chemistry.chemical_compound chemistry Zwitterion General Materials Science Carboxylate Pyridinium Isomerization |
| Zdroj: | CrystEngComm. 20:6126-6132 |
| ISSN: | 1466-8033 |
| DOI: | 10.1039/c8ce01255e |
| Popis: | Through structural modification of 2-anilinonicotinic acid by isomerization, the ΔpKa between the carboxylic acid and pyridinium NH increased dramatically over the threshold to form zwitterions in the newly designed 4-anilinonicotinic acids. This in turn led to the formation of a hydrogen bond between carboxylate and pyridinium NH, and the absence of two commonly observed synthons, i.e., the acid–acid homosynthon and acid–pyridine heterosynthon. The new synthon has a stronger hydrogen bond than the acid–acid homosynthon and the acid–pyridine heterosynthon, as suggested by theoretical calculations. This, together with the much larger ΔpKa, explains its formation. |
| Databáze: | OpenAIRE |
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