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

Research output: Contribution to journalArticlepeer-review

7 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 languageEnglish
Pages (from-to)4346-4357
Number of pages12
JournalCrystal Growth and Design
Volume20
Issue number7
DOIs
StatePublished - Jul 1 2020

Bibliographical note

Publisher Copyright:
© 2020 American Chemical Society.

ASJC Scopus subject areas

  • General Chemistry
  • General Materials Science
  • Condensed Matter Physics

Fingerprint

Dive into the research topics of 'Steric Effect Determines the Formation of Lactam-Lactam Dimers or Amide C.O···NH (Lactam) Chain Motifs in N-Phenyl-2-hydroxynicotinanilides'. Together they form a unique fingerprint.

Cite this