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Issue 40, 2018
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Zwitterion formation and subsequent carboxylate–pyridinium NH synthon generation through isomerization of 2-anilinonicotinic acid

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Abstract

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.

Graphical abstract: Zwitterion formation and subsequent carboxylate–pyridinium NH synthon generation through isomerization of 2-anilinonicotinic acid

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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, 2018,20, 6126-6132
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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. Parkin, T. Li, C. Li, F. Yu and S. Long, CrystEngComm, 2018, 20, 6126
    DOI: 10.1039/C8CE01255E

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