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Isonicotinamide-2-naphthoic acid (1/1).

Lee G Madeley1, Demetrius C Levendis, Andreas Lemmerer

  • 1Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Johannesburg, PO Wits 2050, South Africa.

Acta Crystallographica. Section E, Structure Reports Online
|December 27, 2011
PubMed
Summary
This summary is machine-generated.

This study details the crystal structure of a 1:1 adduct between isonicotinamide and 2-naphthoic acid. It reveals specific hydrogen bonding patterns and molecular conformations, forming a unique four-molecule chain structure.

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Area of Science:

  • Crystal engineering
  • Supramolecular chemistry
  • Organic solid-state chemistry

Background:

  • Understanding intermolecular interactions is crucial for designing novel materials.
  • Hydrogen bonding plays a key role in the self-assembly of organic molecules.
  • The specific interactions of isonicotinamide and 2-naphthoic acid have not been fully elucidated in a 1:1 adduct.

Purpose of the Study:

  • To determine the crystal structure of the 1:1 adduct of isonicotinamide and 2-naphthoic acid.
  • To analyze the hydrogen bonding network and molecular conformation within the adduct.
  • To investigate the self-assembly behavior driven by specific intermolecular forces.

Main Methods:

  • Single-crystal X-ray diffraction was employed to obtain the precise molecular structure.
  • Analysis of torsion angles (C-C-C-N and C-C-C-O) provided insights into molecular geometry.
  • Hydrogen bond analysis (N-H⋯O and O-H⋯N) identified the specific intermolecular interactions.

Main Results:

  • The 1:1 adduct exhibits a unique crystal structure with specific torsion angles: C-C-C-N (25.11°) and C-C-C-O (10.9°).
  • Isonicotinamide molecules form dimers through N-H⋯O hydrogen bonds.
  • A centrosymmetric four-molecule chain is formed via O-H⋯N hydrogen bonds between 2-naphthoic acid and isonicotinamide, further cross-linked by N-H⋯O bonds.

Conclusions:

  • The study elucidates the detailed supramolecular architecture of the isonicotinamide-2-naphthoic acid 1:1 adduct.
  • Specific hydrogen bonding interactions dictate the formation of a complex, centrosymmetric chain structure.
  • This detailed structural understanding contributes to the field of crystal engineering and rational design of organic materials.