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Zwitterion Formation and Subsequent Carboxylate-Pyridinium NH Synthon Generation through Isomerization of 2-Anilinonicotinic Acid

Abstract

Through structural modification of 2-anilinonicotinic acid by isomerization, the △pKa between the carboxylic acid and pyridinium NH increased dramatically over the threshold to form zwitterion in the newly designed 4-anilinonicotinic acids, which led to the formation of hydrogen bond between carboxylate and pyridinium NH, and the two commonly observed synthons, i.e. the acid-acid homosynthon and acid-pyridine heterosynthon were no longer observed. The new synthon has a stronger hydrogen-bond strength than that of the acid-acid homosynthon and the acid-pyridine heterosynthon, as suggested by theoretical calculations, which, together with the much larger △pKa, explains its formation.

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Publication details

The article was received on 28 Jul 2018, accepted on 11 Sep 2018 and first published on 12 Sep 2018


Article type: Communication
DOI: 10.1039/C8CE01255E
Citation: CrystEngComm, 2018, Accepted Manuscript
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    Zwitterion Formation and Subsequent Carboxylate-Pyridinium NH Synthon Generation through Isomerization of 2-Anilinonicotinic Acid

    P. Yue, C. Dong, M. Zhang, D. Xu, S. R. Parkin, T. Li, C. Li, F. Yu and S. Long, CrystEngComm, 2018, Accepted Manuscript , DOI: 10.1039/C8CE01255E

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