A Thermodynamic and Structural Study of the Interactions of Pyridino- and Diketopyridino-18-Crown-6 Ligands with some Primary Organic Ammonium Cations

Abstract

Equilibrium constant (K), enthalpy change (AH). and entropy change (AS) values have been determined calorimetrically at 25 degC in 90%MeOH-l0%H20 (v/v) for the interactions of pyridino-18crown-6 (Pl8C6) and diketopyridino-18- crown-6 (K2P18C6) with perchlorate salts of ammonium, benzylammonium. Alpha- Phenylethylammonium, Beta-phenylethylammonium, and Alpha(1-naphthyl) ethylstructure of the complex or P18C6 with benzylammonium perchlorate was determined by X-ray crystallography. The 1H 1D and 2D NMR spectra of some of these complexes were used to elucidate their structural features in solution. The log K values for the interaction of the ammonium rations with P18C6 arc larger than those with K2Pl8C6, probably due to the higher degree of structural flexibility of P18C6. Ligand K2Pl8C6 displays appreciable Pi-Pi interaction with Alpha-(1-naphthyl) ethylammonium cation, but not with Alpha-phenylethylammonium cation.

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Document Details

Document Type
Technical Report
Publication Date
Mar 15, 1992
Accession Number
ADA248056

Entities

People

  • C. Y. Zhu
  • J. S. Bradshaw
  • N. K. Dalley
  • Reed Izatt

Organizations

  • Brigham Young University

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  • Air Platforms
  • C4I

DTIC Thesaurus Topics

  • Chemical Shifts
  • Chemical Synthesis
  • Chemistry
  • Classification
  • Crown Ethers
  • Crystal Structure
  • Crystals
  • Diseases And Disorders
  • Hydrogen Bonds
  • Materials
  • Military Research
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  • Chemistry

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  • Organic Chemistry