A series of N-phenyl-2-hydroxynicotinanilides (PHNAs) have been synthesized, and their crystal structures have been investigated. The identity of these compounds is revealed to be the tautomer of PHNAs, i.e., 2-oxo-1,2-dihydropyridine-3-carboxylic acid phenylamides, compounds with both amide and lactam functionalities. Among these compounds, those with no or negligible steric hindrance take a near planar conformation and form lactam-lactam dimers, not the widely observed amide NH···O=C hydrogen bond chains, while those with steric hindrance take a twisted conformation and form an amide NH···O=C (lactam) hydrogen bond. A succinct theoretic study combining conformational analysis and molecular electrostatic potential surfaces (MEPS) survey provided a reasonable explanation of the formation of these two different hydrogen bond motifs.
|Number of pages||12|
|Journal||Crystal Growth and Design|
|State||Published - Jul 1 2020|
Bibliographical noteFunding Information:
H.L. and S.L. thank Natural Science Foundation of Hubei Province for financial support (2014CFB787). X.Y. is grateful for the sponsorship from Innovation Fund of the Graduate School of WIT (CX2019018). Z.Y. thanks the National Natural Science Foundation of China for providing financial support (81172965 and 81321004).
© 2020 American Chemical Society.
ASJC Scopus subject areas
- Chemistry (all)
- Materials Science (all)
- Condensed Matter Physics