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Factors influencing enantiomeric recognition of primary alkylammonium salts by pyridino-18-crown-6 type ligands

  • Reed M. Izatt
  • Tingmin Wang
  • Jon K. Hathaway
  • Xian X. Zhang
  • Janet C. Curtis
  • Jerald S. Bradshaw
  • Cheng Y. Zhu
  • Peter Huszthy
Research Communication

Abstract

Equilibrium constant (K), enthalpy change (ΔH), and entropy change (ΔS) values were determined for the interactions of a series of chiral pyridino-18-crown-6 type ligands with enantiomers of several primary alkylammonium salts in various solvents. Good enantiomeric recognition in terms of Δ logK was observed in many systems with Δ logK values greater than 0.4. The extent of enantiomeric recognition and the stabilities of the chiral crown ether-ammonium salt complexes were found to depend on the rigidity of the macrocyclic frame of the ligand, the type and arrangement of the donor atoms on the ligand, the bulkiness of the substituents on the ligand's chiral centers, the location of the chiral centers on the ligand, and the solvent. The effects of these factors on the extent of enantiomeric recognition and on the stabilities of the complexes were examined for the systems studied.

Key words

Enantiomeric recognition pyridino-18-crown-6 type ligands primary alkylammonium salts equilibrium constant (Kenthalpy change (ΔHentropy change (ΔSNMR titration calorimetry 

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Copyright information

© Kluwer Academic Publishers 1994

Authors and Affiliations

  • Reed M. Izatt
    • 1
  • Tingmin Wang
    • 1
  • Jon K. Hathaway
    • 1
  • Xian X. Zhang
    • 1
  • Janet C. Curtis
    • 1
  • Jerald S. Bradshaw
    • 2
  • Cheng Y. Zhu
    • 1
  • Peter Huszthy
    • 3
  1. 1.Analytical ChemistryMarion Merrell Dow, Inc.Kansas CityUSA
  2. 2.Department of ChemistryBrigham Young UniversityProvoUSA
  3. 3.Institute of Organic ChemistryTechnical UniversityBudapestHungary

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