Steric Effect Determines the Formation of Lactam-Lactam Dimers or Amide C.O···NH (Lactam) Chain Motifs in N-Phenyl-2-hydroxynicotinanilides

H. Liu; X. Yang; S. Cao; F. Yu; S. Long; J. Chen; M. Zhang; S. Parkin; T. Li; Z. Yang

doi:10.1021/acs.cgd.0c00023

Steric Effect Determines the Formation of Lactam-Lactam Dimers or Amide C.O···NH (Lactam) Chain Motifs in N-Phenyl-2-hydroxynicotinanilides

H. Liu, X. Yang, S. Cao, F. Yu, S. Long, J. Chen, M. Zhang, S. Parkin, T. Li, Z. Yang

Chemistry

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	4346-4357
Number of pages	12
Journal	Crystal Growth and Design
Volume	20
Issue number	7
DOIs	https://doi.org/10.1021/acs.cgd.0c00023
State	Published - Jul 1 2020

Bibliographical note

Funding 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).

Publisher Copyright:
© 2020 American Chemical Society.

ASJC Scopus subject areas

Chemistry (all)
Materials Science (all)
Condensed Matter Physics

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10.1021/acs.cgd.0c00023

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title = "Steric Effect Determines the Formation of Lactam-Lactam Dimers or Amide C.O···NH (Lactam) Chain Motifs in N-Phenyl-2-hydroxynicotinanilides",

abstract = "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.",

author = "H. Liu and X. Yang and S. Cao and F. Yu and S. Long and J. Chen and M. Zhang and S. Parkin and T. Li and Z. Yang",

note = "Funding 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). Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

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doi = "10.1021/acs.cgd.0c00023",

language = "English",

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AU - Liu, H.

AU - Yang, X.

AU - Cao, S.

AU - Yu, F.

AU - Long, S.

AU - Chen, J.

AU - Zhang, M.

AU - Parkin, S.

AU - Li, T.

AU - Yang, Z.

N1 - Funding 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). Publisher Copyright: © 2020 American Chemical Society.

PY - 2020/7/1

Y1 - 2020/7/1

N2 - 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.

AB - 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.

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Steric Effect Determines the Formation of Lactam-Lactam Dimers or Amide C.O···NH (Lactam) Chain Motifs in N-Phenyl-2-hydroxynicotinanilides

Abstract

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