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

8 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

Publisher Copyright:
© 2020 American Chemical Society.

ASJC Scopus subject areas

General Chemistry
General Materials Science
Condensed Matter Physics

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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",

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year = "2020",

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

language = "English",

volume = "20",

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T1 - Steric Effect Determines the Formation of Lactam-Lactam Dimers or Amide C.O···NH (Lactam) Chain Motifs in N-Phenyl-2-hydroxynicotinanilides

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.

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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U2 - 10.1021/acs.cgd.0c00023

DO - 10.1021/acs.cgd.0c00023

M3 - Article

AN - SCOPUS:85087612782

SN - 1528-7483

VL - 20

SP - 4346

EP - 4357

JO - Crystal Growth and Design

JF - Crystal Growth and Design

IS - 7

ER -

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

Abstract

Bibliographical note

ASJC Scopus subject areas

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