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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
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2-[2-(2-Pyrid-yl)eth-yl]isoindolinium perchlorate.

Ray J Butcher1, Yohannes T Tesema, Teshome B Yisgedu

  • 1Department of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary

This study details the crystal structure of a protonated isoindoline salt, revealing an intramolecular hydrogen bond and weak interactions between the cation and perchlorate anion. The perchlorate anion

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Published on: April 24, 2018

Area of Science:

  • Crystallography
  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Isoindoline derivatives are important scaffolds in medicinal chemistry.
  • Understanding the solid-state behavior of organic salts is crucial for drug formulation.
  • Perchlorate salts are commonly used counterions in organic synthesis.

Purpose of the Study:

  • To elucidate the crystal structure of a specific isoindoline perchlorate salt.
  • To investigate the nature of intermolecular interactions within the crystal lattice.
  • To characterize the disorder of the perchlorate anion.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Structural analysis included identification of hydrogen bonding and other weak interactions.
  • Disorder of the perchlorate anion was modeled and refined.

Main Results:

  • The crystal structure confirmed the protonation of the isoindoline nitrogen atom.
  • An intramolecular N-H⋯N hydrogen bond was identified within the cation.
  • Weak N-H⋯O and C-H⋯O interactions were observed between the cation and perchlorate anion.
  • The perchlorate anion exhibited significant positional disorder over four sites.

Conclusions:

  • The crystal packing is influenced by both intramolecular and intermolecular interactions.
  • The observed disorder of the perchlorate anion is a key structural feature.
  • This structural information contributes to the understanding of isoindoline salt behavior in the solid state.