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3-

Pavlovic1, Sosa

  • 1Chemistry Department, Laboratory of General and Inorganic Chemistry, Faculty of Science, University of Zagreb, Ul. kralja Zvonimira 8, 10000 Zagreb, Croatia. pavlovic@chem.pmf.hr.

Acta Crystallographica. Section C, Crystal Structure Communications
|September 15, 2000
PubMed
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This study reveals a ketoamino tautomer in a novel compound, featuring intramolecular hydrogen bonds and near-planar geometry. Intermolecular hydrogen bonds link molecules into infinite chains, offering insights into crystal structure and molecular interactions.

Area of Science:

  • Crystallography
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Understanding tautomerism is crucial for predicting chemical properties.
  • Intramolecular and intermolecular hydrogen bonding significantly influences molecular and crystal structures.

Purpose of the Study:

  • To elucidate the tautomeric form and hydrogen bonding network of the title compound, C(18)H(13)NO(3).
  • To analyze the molecular geometry and packing in the crystalline state.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of bond lengths, angles, and hydrogen bond distances provided structural insights.

Main Results:

  • The compound exists as a ketoamino tautomer with a short intramolecular N-H...O hydrogen bond (2.531 Å).

Related Experiment Videos

  • Pi-electron delocalization enhances the intramolecular hydrogen bond.
  • The molecule exhibits near-planar geometry with a dihedral angle of 4.41(7)° between the naphthaldimine and 3-carboxyphenyl fragments.
  • Infinite chains are formed via intermolecular O-H...O hydrogen bonds between carboxyl and keto oxygen atoms along twofold screw axes parallel to b.
  • Conclusions:

    • The ketoamino tautomer and extensive hydrogen bonding dictate the compound's solid-state structure.
    • The interplay of intramolecular and intermolecular forces governs the formation of extended supramolecular chains.